347
Pathway
Retinol Metabolism
Retinol is part of the vitamin A family, and is known as vitamin A1, and in a dietary context it is a type of preformed vitamin A. As with other preformed vitamin A's, it can be obtained from animal sources, with the highest concentrations coming from animal liver, with other sources being fish and dairy products. Other forms of vitamin A include retinal, its aldehyde form, retinoic acid, its acid form, and reinyl ester, its ester form. Additionally, herbivores and omnivores can obtain provitamin A from things such as alpha-, beta- and gamma-carotene, which can be converted to retinol as needed by the body.
Retinol can be used in the body to form retinyl ester via diacylglycerol O-acyltransferase 1 and acyl-CoA wax akcohol acyltransferase 1 which both use acetyl-CoA as a reactant and produce CoA in addition to the retinyl ester. IT can also be produced by lecithin retinol acyltransferase, which uses a phosphatidylcholine molecule, and produces glycerophosphocholine. All of these reactions take place in the endoplasmic reticulum. Retinyl ester can also be converted back to retinol by patatin-like phospholipase domain-containing protein 4 as the enzyme in a reaction that also converts a diacylglycerol to a triacylglycerol. Alternately, retinyl ester can interact with retinoid isomerohydrolase to form 11-cis-retinol.
11-cis-retinol can be converted to retinyl palmitate by either diacylglycerol O-acyltransferase 1 or acyl-CoA wax alcohol acyltransferase 1 in the endoplasmic reticulum, which both add the acetyl group onto 11-cis-retinol, forming CoA as a side product. Alternatively, retinyl palmitate can be formed by lecithin retinol acyltransferase, which takes a molecule of phosphatidylcholine, and produces glycerophosphocholine in addition to the retinyl palmitate.
Rhodopsin, a photosensitive protein found in the retina, can be converted to bathorhodopsin, which has previously been known as prelumirhodopsin. This conversion is caused by the absorption of light into the retinal portion of the protein complex, which then isomerizes, forcing the protein to change shape to accomodate this. Bathorhodopsin almost immediately converts to lumirhodopsin, which then converts to metarhodopsin, and at this point, the retinal is in its all-trans configuration. All-trans retinal can also be formed from 11-cis-retinaldehyde, also known as 11-cis-retinal, via dehydrogenase/reductase SDR family member 4 or retinol dehydrogenase 12 in the cell, as well as retinol dehydrogenases 8 and 16, short-chain dehydrogenase/reductase 3 or dehydrogenase/reductase SRD family member 9 in the endoplasmic reticulum. Two molecules of retinal can also be formed from beta-carotene, after its interaction with betabeta-carotene 15,15'-monooxygenase, or from retinol via retinol dehydrogenase 11 in the endoplasmic reticulum. Additionally, 11-cis-retinaldehyde can reversibly form all-trans retinal via interaction with alcohol dehydrogenase 1A. 11-cis-retinaldehyde is also in the conformation found in rhodopsin, and can be used to create more rhodopsin complexes. 11-cis-retinaldehyde can also be converted to 11-cis-retinol by retinol dehydrogenase in the endoplasmic reticulum.
Retinol can also isomerize and form 9-cis-retinol, which can then be reversibly oxidized to form 9-cis-retinal by interacting with either retinol dehydrogenase 11 or dehydrogenase/reductase SDR family member 4. 9-cis-retinal can then be further oxidized to 9-cis-retinoic acid by retinal dehydrogenase 1 or 2. 9-cis-retinoic acid can also be formed from the isomerization of all-trans retinoic acid, which in turn is formed by the oxidation of retinol by either of retinal dehydrogenase 1 or 2.
All-trans retinoic acid can also be glucuronidated to form retinoyl b-glucuronide, in a reaction catalyzed by a multiprotein chaperone complex including UDP-glucuronosyltransferase 1-1 in the endoplasmic reticulum.
Finally, in the endoplasmic reticulum, all-trans-retinoic acid can undergo epoxidation to form all-trans-5,6-epoxyretinoic acid by interaction with a complex of cytochrome P450 proteins, or hydroxylated to either 4-hydroxyretinoic acid or all-trans-18-hydroxyretinoic acid by cytochrome P450 26A1. In one last reqction, 4-hydroxyretinoic acid can be oxidized once again by cytochrome P450 26A1 to form 4-oxo-retinoic acid.
Metabolic
PW000164
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347
Retinol Metabolism
Retinol is part of the vitamin A family, and is known as vitamin A1, and in a dietary context it is a type of preformed vitamin A. As with other preformed vitamin A's, it can be obtained from animal sources, with the highest concentrations coming from animal liver, with other sources being fish and dairy products. Other forms of vitamin A include retinal, its aldehyde form, retinoic acid, its acid form, and reinyl ester, its ester form. Additionally, herbivores and omnivores can obtain provitamin A from things such as alpha-, beta- and gamma-carotene, which can be converted to retinol as needed by the body.
Retinol can be used in the body to form retinyl ester via diacylglycerol O-acyltransferase 1 and acyl-CoA wax akcohol acyltransferase 1 which both use acetyl-CoA as a reactant and produce CoA in addition to the retinyl ester. IT can also be produced by lecithin retinol acyltransferase, which uses a phosphatidylcholine molecule, and produces glycerophosphocholine. All of these reactions take place in the endoplasmic reticulum. Retinyl ester can also be converted back to retinol by patatin-like phospholipase domain-containing protein 4 as the enzyme in a reaction that also converts a diacylglycerol to a triacylglycerol. Alternately, retinyl ester can interact with retinoid isomerohydrolase to form 11-cis-retinol.
11-cis-retinol can be converted to retinyl palmitate by either diacylglycerol O-acyltransferase 1 or acyl-CoA wax alcohol acyltransferase 1 in the endoplasmic reticulum, which both add the acetyl group onto 11-cis-retinol, forming CoA as a side product. Alternatively, retinyl palmitate can be formed by lecithin retinol acyltransferase, which takes a molecule of phosphatidylcholine, and produces glycerophosphocholine in addition to the retinyl palmitate.
Rhodopsin, a photosensitive protein found in the retina, can be converted to bathorhodopsin, which has previously been known as prelumirhodopsin. This conversion is caused by the absorption of light into the retinal portion of the protein complex, which then isomerizes, forcing the protein to change shape to accomodate this. Bathorhodopsin almost immediately converts to lumirhodopsin, which then converts to metarhodopsin, and at this point, the retinal is in its all-trans configuration. All-trans retinal can also be formed from 11-cis-retinaldehyde, also known as 11-cis-retinal, via dehydrogenase/reductase SDR family member 4 or retinol dehydrogenase 12 in the cell, as well as retinol dehydrogenases 8 and 16, short-chain dehydrogenase/reductase 3 or dehydrogenase/reductase SRD family member 9 in the endoplasmic reticulum. Two molecules of retinal can also be formed from beta-carotene, after its interaction with betabeta-carotene 15,15'-monooxygenase, or from retinol via retinol dehydrogenase 11 in the endoplasmic reticulum. Additionally, 11-cis-retinaldehyde can reversibly form all-trans retinal via interaction with alcohol dehydrogenase 1A. 11-cis-retinaldehyde is also in the conformation found in rhodopsin, and can be used to create more rhodopsin complexes. 11-cis-retinaldehyde can also be converted to 11-cis-retinol by retinol dehydrogenase in the endoplasmic reticulum.
Retinol can also isomerize and form 9-cis-retinol, which can then be reversibly oxidized to form 9-cis-retinal by interacting with either retinol dehydrogenase 11 or dehydrogenase/reductase SDR family member 4. 9-cis-retinal can then be further oxidized to 9-cis-retinoic acid by retinal dehydrogenase 1 or 2. 9-cis-retinoic acid can also be formed from the isomerization of all-trans retinoic acid, which in turn is formed by the oxidation of retinol by either of retinal dehydrogenase 1 or 2.
All-trans retinoic acid can also be glucuronidated to form retinoyl b-glucuronide, in a reaction catalyzed by a multiprotein chaperone complex including UDP-glucuronosyltransferase 1-1 in the endoplasmic reticulum.
Finally, in the endoplasmic reticulum, all-trans-retinoic acid can undergo epoxidation to form all-trans-5,6-epoxyretinoic acid by interaction with a complex of cytochrome P450 proteins, or hydroxylated to either 4-hydroxyretinoic acid or all-trans-18-hydroxyretinoic acid by cytochrome P450 26A1. In one last reqction, 4-hydroxyretinoic acid can be oxidized once again by cytochrome P450 26A1 to form 4-oxo-retinoic acid.
Metabolic
1
160
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Pathway
161
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
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Pathway
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Astrom A, Tavakkol A, Pettersson U, Cromie M, Elder JT, Voorhees JJ: Molecular cloning of two human cellular retinoic acid-binding proteins (CRABP). Retinoic acid-induced expression of CRABP-II but not CRABP-I in adult human skin in vivo and in skin fibroblasts in vitro. J Biol Chem. 1991 Sep 15;266(26):17662-6.
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Pathway
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Roberts AB, Nichols MD, Newton DL, Sporn MB: In vitro metabolism of retinoic acid in hamster intestine and liver. J Biol Chem. 1979 Jul 25;254(14):6296-302.
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Pathway
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Gutierrez-Mazariegos J, Schubert M, Laudet V: Evolution of retinoic acid receptors and retinoic acid signaling. Subcell Biochem. 2014;70:55-73. doi: 10.1007/978-94-017-9050-5_4.
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Blaner WS, Li Y, Brun PJ, Yuen JJ, Lee SA, Clugston RD: Vitamin A Absorption, Storage and Mobilization. Subcell Biochem. 2016;81:95-125. doi: 10.1007/978-94-024-0945-1_4.
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Belyaeva OV, Wu L, Shmarakov I, Nelson PS, Kedishvili NY: Retinol dehydrogenase 11 is essential for the maintenance of retinol homeostasis in liver and testis in mice. J Biol Chem. 2018 May 4;293(18):6996-7007. doi: 10.1074/jbc.RA117.001646. Epub 2018 Mar 22.
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Zhang M, Hu P, Napoli JL: Elements in the N-terminal signaling sequence that determine cytosolic topology of short-chain dehydrogenases/reductases. Studies with retinol dehydrogenase type 1 and cis-retinol/androgen dehydrogenase type 1. J Biol Chem. 2004 Dec 3;279(49):51482-9. doi: 10.1074/jbc.M409051200. Epub 2004 Sep 7.
347
Pathway
1
Cell
CL:0000000
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CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
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Epithelial Cell
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Platelet
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6
Myocyte
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9
Pancreatic Beta Cell
CL:0000169
29
Pneumocyte
CL:0000322
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
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African clawed frog
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
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Nitzschia4
25
Escherichia coli (strain K12)
83333
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49
Bathymodiolus platifrons
220390
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Deep sea mussel
15
Plasmodium falciparum
5833
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138
human
0046323
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1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
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Cytoplasm
GO:0005737
7
Endoplasmic Reticulum Membrane
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Peroxisome
GO:0005777
12
Mitochondrial Inner Membrane
GO:0005743
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Lysosome
GO:0005764
13
Endoplasmic Reticulum
GO:0005783
16
Lysosomal Lumen
GO:0043202
35
Chloroplast
GO:0009507
10
Cell Membrane
GO:0005886
31
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GO:0005620
19
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GO:0016529
36
Membrane
GO:0016020
32
Inner Membrane
GO:0070258
39
Mitochondrial membrane
GO:0031966
8
Smooth Endoplasmic Reticulum
GO:0005790
14
Mitochondrial Outer Membrane
GO:0005741
27
Peroxisome Membrane
GO:0005778
11
Extracellular Space
GO:0005615
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
24
Mitochondrial Intermembrane Space
GO:0005758
1
Liver
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9
11
Heart
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10
5
cardiocyte
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Adrenal Medulla
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8
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Stomach
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Blood Vessel
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Muscle
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18
18
Pancreas
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Lung
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360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
412
1
2
5
PW_BS000115
409
11
5
PW_BS000115
415
18
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
436
25
5
PW_BS000115
446
1
2
17
PW_BS000115
137
11
17
PW_BS000137
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
483
11
10
PW_BS000115
487
18
10
1
PW_BS000115
208
11
6
PW_BS000024
504
18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
790
6
11
1
PW_BS000524
834
6
1
1
1
PW_BS000549
19
3
5
1
3
PW_BS000019
16
2
1
2
PW_BS000016
42
24
1
1
PW_BS000042
345
24
12
1
PW_BS000028
418
24
5
1
PW_BS000115
454
24
17
1
PW_BS000115
489
24
10
1
PW_BS000115
506
24
6
1
PW_BS000115
78
8
1
1
PW_BS000078
1056
9
1
1
6
PW_BS000578
615
1
7
15
1
PW_BS000503
847
1
1
PW_BS000549
973
1
7
1
5
PW_BS000569
996
1
13
1
5
PW_BS000569
392
1
7
1
PW_BS000171
69
18
10
1
9
PW_BS000069
1321
26
7
1
29
PW_BS000588
1399
26
7
1
1
PW_BS000630
325
1
7
23
1
PW_BS000024
844
13
138
1
PW_BS000549
608
32
1
PW_BS000501
1121
25
7
1
7
PW_BS000580
1281
1
13
15
5
PW_BS000588
1448
11-cis-Retinaldehyde
HMDB0002152
Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly (http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0260.shtml).
564-87-4
C02110
5280490
16066
CPD-881
4444130
C/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
NCYCYZXNIZJOKI-IOUUIBBYSA-N
284.4357
284.214015518
FDB022871
11-cis-retinal;Cis-11-retinal;(2e,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;11-cis-retinene;11-cis-vitamin a aldehyde
PW_C001448
C-RetAl
3189
2
78782
132
122528
124
125089
118
126680
299
128260
388
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H27N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-N
663.4251
663.109121631
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
140757
185
1048
Retinal
HMDB0001358
Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration.
116-31-4
C00376
638015
17898
CPD-881
553582
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
NCYCYZXNIZJOKI-OVSJKPMPSA-N
284.4357
284.214015518
FDB022576
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;All-e-retinal;All-epsilon-retinal;All-trans-retinal;All-trans-retinaldehyde;All-trans-vitamin a aldehyde;All-trans-retinene;Axerophthal;E-retinal;Retinal;Retinaldehyde;Retinene;Retinene 1;Vitamin a aldehyde;Vitamin a1 aldehyde;Alpha-retinene;Epsilon-retinal;Trans-retinal;Trans-vitamin a aldehyde
PW_C001048
Retinal
3190
2
78783
132
122529
124
125090
118
126681
299
128261
388
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
665.441
665.124771695
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
140759
185
9795
Zinc
HMDB0015532
Zinc is an essential element, necessary for sustaining all life. It is a trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen cell types in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system, and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Zinc deficiency is associated with anemia, short stature, hypogonadism, impaired wound healing, and geophagia. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature and shows that just micromolar amounts of the free ion kill some organisms.
7440-66-6
23994
27363
22430
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
65.409
63.929146578
30zn;Cinc;Zincum;Zink;Zn;Zn(ii);Zn2+
PW_C009795
Zinc
57
8
1711
2
1904
3
2137
17
2154
49
3610
29
4083
7
4469
18
4543
14
4999
31
6689
107
6690
101
6699
108
7020
160
11758
115
12229
151
12633
65
42397
315
42399
318
77030
253
78023
132
78328
112
78811
111
120119
124
120898
122
122308
407
122852
118
123469
135
124860
119
125486
299
126474
481
127023
388
127317
205
128043
206
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-N
743.405
743.075452041
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
140709
168
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
ACFIXJIJDZMPPO-NNYOXOHSSA-N
745.4209
745.091102105
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
140706
168
2665
11-cis-Retinol
HMDB0006216
Cis-11-retinol is produce from vitamin A cycle driven by interphotoreceptor retinoid binding protein(IRBP). cis-11-retinol is released from retinal pigment epithelium(RPE) membranes. (PMID: 10655150). Retinoid metabolism of RPE cells freshly isolated by trypsinization showed no 11- cis -retinal and little 11- cis -retinol formation. Nondamaged cells cultured on thermally responsive surfaces detached in sheets upon temperature change. They showed metabolism similar to that of cells freshly isolated by nonenzymatic means. After trypsinization, confluent cultures dissociated into individual cells, but these cells showed poor retinoid metabolism, including no detectable retinyl esters or 11- cis -retinoid isomers. (PMID: 10375454).
22737-96-8
C00899
5280382
16302
CPD-882
4444073
C\C(=C/CO)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
FPIPGXGPPPQFEQ-IOUUIBBYSA-N
286.4516
286.229665582
FDB023840
11-cis-vitamin a alcohol;Cis-11-retinol
PW_C002665
C-retol
3198
2
78784
132
122536
124
125097
118
126686
299
128265
388
4838
PC(24:1(15Z)/15:0)
HMDB0008790
PC(24:1(15Z)/15:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:1(15Z)/15:0), in particular, consists of one chain of nervonic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The nervonic acid moiety is derived from fish oils, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
C00157
53479491
PHOSPHATIDYLCHOLINE
24767449
CCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
C47H92NO8P
InChI=1S/C47H92NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-31-33-35-37-39-46(49)53-43-45(44-55-57(51,52)54-42-41-48(3,4)5)56-47(50)40-38-36-34-32-29-19-17-15-13-11-9-7-2/h20-21,45H,6-19,22-44H2,1-5H3/b21-20-/t45-/m1/s1
SKYTWJRHKLHTDQ-ULOIKCHLSA-N
830.209
829.656055437
C00157
1-nervonoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine;Gpcho(24:1/15:0);Gpcho(24:1n9/15:0);Gpcho(24:1w9/15:0);Gpcho(39:1);Lecithin;Pc(24:1/15:0);Pc(24:1n9/15:0);Pc(24:1w9/15:0);Pc(39:1);Phosphatidylcholine(24:1/15:0);Phosphatidylcholine(24:1n9/15:0);Phosphatidylcholine(24:1w9/15:0);Phosphatidylcholine(39:1)
PW_C004838
PC241
3200
2
21892
49
21893
309
25365
18
78785
132
122537
124
125098
118
126687
299
128266
388
1948
Retinyl palmitate
HMDB0003648
Retinyl palmitate, or vitamin A palmitate, is a common vitamin supplement, with formula C36H60O2. It is available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol and Palmitate. Retinyl palmitate is an alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.
79-81-2
C02588
5280531
17616
CPD-523
4444162
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C36H60O2
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
VYGQUTWHTHXGQB-FFHKNEKCSA-N
524.8604
524.459331164
FDB013831
All-trans-retinol palmitate;All-trans-retinyl palmitate;All-trans-vitamin a palmitate;Aquapalm;Aquasol a;Arovit;Axerophthol palmitate;Dispatabs tabs;Ester found in fish liver oils;Lutavit a 500 plus;Myvak;Myvax;Optovit a;Optovit-a;Retinol palmitate;Retinyl hexadecanoate;Retinyl hexadecanoic acid;Retinyl palmitate;Retinyl palmitic acid;Testavol s;Vitamin a palmitate;Vitazyme a;Trans-retinol palmitate;Trans-retinyl palmitate;All-trans-retinyl hexadecanoate;All-trans-retinyl hexadecanoic acid;All-trans-retinyl palmitic acid;Retinol palmitic acid;Vitamin a palmitic acid
PW_C001948
Retylpm
3201
2
78786
132
122538
124
125099
118
126688
299
128267
388
59
Glycerophosphocholine
HMDB0000086
Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.
28319-77-9
C00670
71920
16870
GLYCERYLPHOSPHORYLCHOLINE
64931
C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO
C8H20NO6P
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m1/s1
SUHOQUVVVLNYQR-MRVPVSSYSA-N
257.223
257.102824366
FDB021802
2-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-n,n,n-trimethyl-ethanaminium inner salt;Choline alfoscerate;Choline glycerophosphate;Gpc;Gpcho;Glycerol 3-phosphocholine;Glycerol phosphorylcholine;Glycerol-3-phosphatidylcholine;Glycerophosphatidylcholine;Glycerophosphocholine;Glycerophosphorylcholine;Hydrogen glycerophosphate choline;L-choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt;L-alpha-glycerophosphocholine;L-alpha-glycerophosphorylcholine;L-alpha-glycerylphosphorylcholine;Sn-glycero-3-phosphocholine;A-glycerophosphorylcholine;A-glycerylphosphorylcholine;Alpha-glycerophosphorylcholine;Alpha-glycerylphosphorylcholine
PW_C000059
GPC
3202
2
68683
225
78787
132
122539
124
125100
118
126689
299
128268
388
940
Acetyl-CoA
HMDB0001206
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
72-89-9
C00024
444493
15351
ACETYL-COA
392413
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C23H38N7O17P3S
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
ZSLZBFCDCINBPY-ZSJPKINUSA-N
809.571
809.125773051
FDB022491
Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme a
PW_C000940
Ac-CoA
213
4
385
8
842
3
2416
2
2446
5
2896
17
3340
11
4840
14
5278
103
5476
124
5733
108
6025
155
6077
161
6386
1
6470
178
6923
160
7106
163
7291
198
7460
222
8245
151
8277
210
12582
226
13012
299
42615
315
77121
133
77291
111
77562
112
77706
132
77994
115
78355
134
78433
334
80007
368
80634
119
80663
376
90124
170
119953
406
120145
405
120304
122
120632
407
122417
408
122626
384
122743
120
122959
135
123137
118
124986
374
125200
121
125343
479
125507
478
125633
297
126564
482
126572
481
126778
480
126886
501
127044
209
127394
205
127665
388
128137
502
128145
206
128374
391
140762
185
1099
Coenzyme A
HMDB0001423
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).
85-61-0
C00010
6816
1146900
CO-A
6557
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
C21H36N7O16P3S
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
767.534
767.115208365
FDB022614
Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
PW_C001099
CoA
211
4
386
8
845
3
879
22
892
17
2407
59
2414
2
2459
5
2813
29
2862
31
3342
11
3351
18
4618
10
4629
58
4842
14
4865
54
4879
6
5232
102
5247
104
5280
103
5477
124
5734
108
5777
101
6023
155
6075
161
6384
1
6468
178
6930
160
6961
162
6973
199
7083
188
7108
163
7293
198
7347
210
7458
222
8229
151
9081
226
9090
224
9124
170
9215
195
13013
299
15318
249
25488
49
42616
315
76907
293
77119
133
77222
134
77230
329
77292
111
77550
132
77555
334
77563
112
77633
336
77672
129
77996
115
78047
332
78056
350
78413
335
78567
130
79259
333
79974
331
80005
368
80620
118
80627
374
80635
119
80665
376
93828
382
93834
383
98674
288
110555
389
110561
390
115842
399
115847
398
119951
406
120147
405
120231
384
120305
122
120634
407
120762
117
121406
123
121421
433
121521
125
121666
429
121682
408
121714
414
122404
422
122741
120
122904
121
122960
135
123965
447
123979
468
124079
136
124220
464
124265
450
124974
375
125341
479
125509
478
125579
480
125592
484
125634
297
126084
481
126549
491
126560
482
126746
300
126884
501
127046
209
127109
391
127301
205
127540
206
127667
388
128121
508
128133
502
128340
395
140751
186
140763
185
140767
891
1935
Retinyl ester
HMDB0003598
Retinyl ester, also known as all-E-retinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Retinyl ester is considered to be a practically insoluble (in water) and relatively neutral molecule. Retinyl ester has been found throughout most human tissues, and has also been primarily detected in blood. Within the cell, retinyl ester is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, retinyl ester is involved in the retinol metabolism pathway. Retinyl ester is also involved in the metabolic disorder called vitamin a deficiency. Retinyl ester is a substrate for Lecithin retinol acyltransferase and Retinal pigment epithelium-specific 65 kDa protein.
C02075
5460164
545914
CPD-437
10607936
CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O
C20H30O2
InChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
WWDMJSSVVPXVSV-YCNIQYBTSA-N
302.451
302.224580204
FDB023204
All-trans-retinyl ester;56-dihydroretinoic acid;All-e-retinoic acid;56-dihydroretinoate;All-e-retinoate
PW_C001935
RetEst
3210
2
78788
132
122543
124
125104
118
126692
299
128272
388
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
18.0153
18.010564686
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
140674
790
140675
834
140755
185
544
Fe2+
HMDB0000692
Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.
15438-31-0
C14818
27284
29033
Ferric-Hydroxamate-Complexes
25394
DB01592
[Fe++]
Fe
InChI=1S/Fe/q+2
CWYNVVGOOAEACU-UHFFFAOYSA-N
55.845
55.934942133
FDB016251
Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)
PW_C000544
Fe2+
398
19
641
3
678
31
692
20
709
8
1777
2
7041
163
7052
160
12060
225
12143
151
77179
132
77740
112
77751
129
77760
341
77782
111
120544
407
120557
414
120570
122
121765
124
123178
119
123191
450
123204
135
124316
118
126143
299
126185
481
127650
388
140710
49
140716
18
209
Vitamin A
HMDB0000305
Vitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.
68-26-8
C00473
445354
17336
RETINOL
393012
DB00162
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
286.4516
286.229665582
FDB013828
(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol;All-trans-retinol;Retinol;Vitamin a1;B-retinol;Beta-retinol;Trans-retinol;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol;All-trans-retinyl alcohol;All-trans-vitamin a alcohol;Alphalin;Chocola a
PW_C000209
Retinol
3220
2
78789
132
122545
124
125106
118
126694
299
128274
388
3195
DG(16:1(9Z)/22:0/0:0)
HMDB0007144
DG(16:1(9Z)/22:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:1(9Z)/22:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.
C00165
9543771
DIACYLGLYCEROL
7822721
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
C41H78O5
InChI=1S/C41H78O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h14,16,39,42H,3-13,15,17-38H2,1-2H3/b16-14-/t39-/m0/s1
BZRVDTDUKMXTCU-QZEPCWIRSA-N
651.055
650.584925606
FDB024338
1-palmitoleoyl-2-behenoyl-sn-glycerol;Dag(16:1/22:0);Dag(16:1n7/22:0);Dag(16:1w7/22:0);Dag(38:1);Dg(16:1/22:0);Dg(16:1n7/22:0);Dg(16:1w7/22:0);Dg(38:1);Diacylglycerol;Diacylglycerol(16:1/22:0);Diacylglycerol(16:1n7/22:0);Diacylglycerol(16:1w7/22:0);Diacylglycerol(38:1);Diglyceride
PW_C003195
DG38:1
3228
2
16473
49
78790
132
84038
331
97837
383
117182
398
122546
124
125107
118
126695
299
128275
388
29134
TG(16:1(9Z)/22:0/16:1(9Z))
HMDB0048523
TG(16:1(9Z)/22:0/16:1(9Z)) is a dipalmitoleic acid triglyceride. Triglycerides (TGs or TAGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:1(9Z)/22:0/16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position, one chain of behenic acid at the C-2 position and one chain of palmitoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)<br />TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.
30777879
[H]C(COC(=O)CCCCCCC\C=C/CCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
C57H106O6
InChI=1S/C57H106O6/c1-4-7-10-13-16-19-22-25-26-27-28-29-30-33-36-39-42-45-48-51-57(60)63-54(52-61-55(58)49-46-43-40-37-34-31-23-20-17-14-11-8-5-2)53-62-56(59)50-47-44-41-38-35-32-24-21-18-15-12-9-6-3/h20-21,23-24,54H,4-19,22,25-53H2,1-3H3/b23-20-,24-21-
SCKPWGYVJPFAGF-XFUYORNGSA-N
887.4479
886.798941124
1-(9z-hexadecenoyl)-2-docosanoyl-3-(9z-hexadecenoyl)-glycerol;1-palmitoleoyl-2-behenoyl-3-palmitoleoyl-glycerol;Tag(16:1/22:0/16:1);Tag(54:2);Tg(16:1/22:0/16:1);Tg(54:2);Tracylglycerol(16:1/22:0/16:1);Tracylglycerol(54:2);Triacylglycerol;Triglyceride
PW_C029134
TG54:2
3229
2
31230
49
78791
132
122547
124
125108
118
126696
299
128276
388
2666
9-cis-Retinol
HMDB0006217
9-cis-retinol is a retinoid. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228).
22737-97-9
C16682
9947823
78272
8123435
C\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
FPIPGXGPPPQFEQ-MKOSUFFBSA-N
286.4516
286.229665582
FDB010848
9-cis retinol;9-cis-retinol;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol;(9cis)-retinol
PW_C002666
9-c-Rol
3231
2
78792
132
122549
124
125110
118
126698
299
128278
388
437
B-Carotene
HMDB0000561
B-Carotene is a carotenoid that is a precursor of vitamin A. It is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (porphyria, erythropoietic). (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Engewood, CO, 1995.) -- Pubchem; Carotene is an orange photosynthetic pigment important for photosynthesis. It is responsible for the orange colour of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol (vitamin A) and comes in two primary forms: alpha- and beta-carotene. gamma-, delta- and epsilon-carotene also exist. Carotene can be stored in the liver and converted to vitamin A as needed. Beta-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of beta-carotene as a dietary supplement (i.e. taken as a pill) is still subject to debate. Beta-carotene is fat-soluble, so a small amount of fat is needed to absorb it into the body. -- Wikipedia.
7235-40-7
C02094
5280489
17579
CPD1F-129
4444129
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
C40H56
InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11-,19-13+,20-14+,27-25+,28-26+,31-17-,32-18+,33-21+,34-22+
OENHQHLEOONYIE-KBPBZLIPSA-N
536.8726
536.438201792
FDB014613
(all-e)-1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis;(all-e)-1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-cyclohexene;All-e-b-carotene;All-epsilon-beta-carotene;All-trans-b-carotene;All-trans-beta-carotene;Betavit;Betacarotene;Carotaben;Carotene base 80s;Food orange 5;Kpmk;Lucaratin;Lucarotin;Lurotin;Provatene;Provatenol;Rovimix b-carotene;Serlabo;Solatene;B-carotene;Beta-carotene;1,1'-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene);Beta-karotin
PW_C000437
b-carot
3233
2
12054
225
73014
27
78793
132
122550
124
125111
118
126699
299
128279
388
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
31.9988
31.989829244
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
2667
9-cis-Retinal
HMDB0006218
In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID: 15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of. unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID: 10893430), in maintaining normal reproduction, and in the immune response (PMID: 8882153). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID: 10322133). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID: 10418975), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID: 8825126, PMID: 12743994).
514-85-2
C16681
6436082
78273
4940758
C/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
NCYCYZXNIZJOKI-MKOSUFFBSA-N
284.4357
284.214015518
FDB023842
9-cis-retinal;9-cis-retinaldehyde;9-cis-vitamin a aldehyde;Isoretinene a;Cis-9-retinal;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;(9cis)-retinal;9-c-retinal;9-cis-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;9-cis-7,11,13-trans-retinal
PW_C002667
9-c-Ral
3235
2
78794
132
122551
124
125113
118
126700
299
128280
388
1600
9-cis-Retinoic acid
HMDB0002369
9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228).
5300-03-8
C15493
449171
50648
395778
DB00523
C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O
C20H28O2
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
300.4351
300.20893014
FDB022982
15-apo-beta-caroten-15-oate;15-apo-beta-caroten-15-oic acid;9-retinoate;9-retinoic acid;9-cis-retinoate;9-cis-retinoic acid;9-cis-tretinoin;A-acido (argentina);Aberel;Aberela [norway];Acide retinoique (french) (dsl);Airol;Aknoten;Alitretinoin;Alitretinoin (usan);Alitretinoin [usan];All-trans- vitamin a1 acid;All-trans-b-retinoate;All-trans-b-retinoic acid;All-trans-beta-retinoate;All-trans-beta-retinoic acid;All-trans-vitamin a acid;Atragen;Avita;Avitoin [norway];B-retinoate;B-retinoic acid;Dermairol;Effederm;Effederm [france];Epi-aberel;Eudyna;Isotretinoin retinoate;Isotretinoin retinoic acid;Panretin;Panretin (tn);Panretin gel;Panretyn;Panrexin;Renova;Retacnyl;Retin a;Retin a (tn);Retin-a;Retin-a micro;Retinoate;Retinoic acid;Retinova;Trans-retinoate;Trans-retinoic acid;Tretinoin;Tretinoin (tn);Tretinoin (jan/usp);Tretinoin [usan:ban:inn];Tretinoin/all-trans retinoate;Tretinoin/all-trans retinoic acid;Tretinoina [inn-spanish];Tretinoine (french) (einecs);Tretinoine [inn-french];Tretinoino [inn-spanish];Tretinoinum [inn-latin];Tretinon;Vesanoid;Vesnaroid;Alpha-acido (argentina);Alpha-vitaminsyre [denmark];Beta-retinoate;Beta-retinoic acid;Trans-vitamin a acid;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;(7e,9z,11e,13e)-retinoic acid;9(z)-retinoic acid;Alitretinoina;Alitretinoine;Alitretinoinum;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(7e,9z,11e,13e)-retinoate;9(z)-retinoate;Aberela;Alpha-vitaminsyre;Avitoin
PW_C001600
Airol
3243
2
78795
132
122552
124
125114
118
126701
299
128281
388
1227
all-trans-Retinoic acid
HMDB0001852
all-trans-Retinoic acid (ATRA) is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
302-79-4
C00777
444795
15367
392618
DB00755
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O2
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
SHGAZHPCJJPHSC-YCNIQYBTSA-N
300.442
300.208930142
FDB022710
(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;Acide retinoique (french);All-(e)-retinoate;All-(e)-retinoic acid;All-trans-retinoate;All-trans-retinoic acid;All-trans-tretinoin;All-trans-vitamin a acid;All-trans-vitamin a1 acid;Retinoate;Retinoic acid;Tretin m;Tretinoine (french);Vitamin a acid;Beta-retinoate;Beta-retinoic acid;Trans-retinoate;Trans-retinoic acid
PW_C001227
T-RetcA
3246
2
78796
132
122554
124
125117
118
126703
299
128282
388
7859
4-Oxoretinol
HMDB0012329
4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846].
62702-55-0
C16683
5289090
4451124
DB02699
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
C20H28O2
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
PLIUCYCUYQIBDZ-RMWYGNQTSA-N
300.4351
300.20893014
C16683
3,7-dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol;4-ketoretinol;4-ketovitamin a(1);4-ketovitamin-a-alcohol;4-ketovitamin-alpha-alcohol;4-oxo-retinol;4-oxorol;4-oxovitamin a1;4-oxovitamin-a-alcohol;4-oxovitamin-alpha-alcohol;4ova1;All-trans-4-oxoretinol;Oxr
PW_C007859
4ORetol
3247
2
78797
132
122555
124
125118
118
126704
299
128284
388
1799
Heme
HMDB0003178
Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.
14875-96-8
C00032
17627
HEME_A
24604415
DB02577
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
C34H32FeN4O4
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
KABFMIBPWCXCRK-RGGAHWMASA-L
616.487
616.177297665
FDB016272
(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematin
PW_C001799
Heme
247
16
308
10
324
8
608
2
766
5
1244
3
1354
49
1413
36
1963
18
2806
29
2938
9
3238
11
3367
26
3421
14
3734
4
4043
31
4823
28
5170
95
5472
123
5485
125
5517
129
5830
141
6246
78
6283
1
6597
151
7044
160
7060
161
7326
213
11835
198
11898
211
12065
164
13009
298
13021
300
42278
17
76915
293
76931
249
77351
111
77364
130
77367
331
77398
332
77517
115
77629
336
77813
334
78380
133
78602
132
78963
112
79932
134
120431
405
120603
408
120955
407
121085
383
121658
429
121746
124
121910
122
122570
406
122691
384
123065
376
123133
447
123144
136
123228
374
123521
119
123650
398
124216
464
124297
118
124463
135
125142
120
125277
121
125742
482
125896
481
126196
299
126499
297
126512
495
126718
479
126827
480
127224
502
127357
206
127632
388
128070
205
128083
395
128086
390
128309
501
128434
391
7207
All-trans-13,14-dihydroretinol
HMDB0011618
All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG).
115797-14-3
C15492
446798
52075
CPD-7247
394057
CC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C20H32O
InChI=1S/C20H32O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-12,17,21H,7,10,13-15H2,1-5H3/b9-6+,12-11+,16-8+
OVBOQVAIYMSUDT-HRYGCDPOSA-N
288.4675
288.245315646
C15492
13,14-dihydro-retinol;13,14-dihydro-all-trans-retinol;13,14-dihydroretinol;All-trans-13,14-dihydroretinol
PW_C007207
ATdhret
3249
2
78798
132
122557
124
125120
118
126706
299
128286
388
1786
Retinoyl b-glucuronide
HMDB0003141
Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.
401-10-5
C11061
5281877
28870
Beta-D-Glucuronides
4445170
O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C26H36O8
InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1
MTGFYEHKPMOVNE-NEFMKCFNSA-N
476.5592
476.241018128
DBMET00561
FDB023112
13-cis-retinoate;13-cis-retinoic acid;13-cis-retinoic acid acyl beta-d-glucuronide;13-cis-retinoic acid acyl beta-delta-glucuronide;13-cis-retinoyl glucuronide;13-cis-retinoyl-beta-d-glucuronide;13-cis-retinoyl-beta-delta-glucuronide;13-cis-retinoyl-beta-glucuronide;9-cis-retinoyl-beta-d-glucuronide;9-cis-retinoyl-beta-delta-glucuronide;All-trans-retinoyl-beta-d-glucuronide;All-trans-retinoyl-beta-delta-glucuronide;All-trans-retinoyl-beta-glucuronide;Glucuronide;Retinoate;Retinoic acid;Retinoic acid beta-d-glucuronide;Retinoic acid beta-delta-glucuronide;Retinoyl beta-glucuronide;Retinoyl glucuronide;Retinoyl-beta-glucuronide;All-trans-retinoyl-b-glucuronide;All-trans-retinoyl-β-glucuronide;1-o-all-trans-retinoyl-b-glucuronate;1-o-all-trans-retinoyl-b-glucuronic acid;1-o-all-trans-retinoyl-beta-glucuronate;1-o-all-trans-retinoyl-β-glucuronate;1-o-all-trans-retinoyl-β-glucuronic acid
PW_C001786
RetybGu
3251
2
78799
132
125122
118
128288
388
2690
4-Hydroxyretinoic acid
HMDB0006254
4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384).
66592-72-1
C16677
6438629
63795
4943093
C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
KGUMXGDKXYTTEY-FRCNGJHJSA-N
316.4345
316.203844762
DBMET00298
FDB023862
4-hydroxy-13-cis-retinoate;4-hydroxy-13-cis-retinoic acid;4-hydroxy-retinoate;4-hydroxy-retinoic acid;4-hydroxy-all-trans-retinoate;4-hydroxy-all-trans-retinoic acid;4-oh-retinoate;4-oh-retinoic acid;All-trans-4-hydroxyretinoate;All-trans-4-hydroxyretinoic acid;Rac-4-hydroxy-all-trans-retinoate;Rac-4-hydroxy-all-trans-retinoic acid;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid;(7e,9e,11e,13e)-4-hydroxyretinoic acid;4-hydroxy-(7e,9e,11e,13e)-retinoic acid;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate;(7e,9e,11e,13e)-4-hydroxyretinoate;4-hydroxy-(7e,9e,11e,13e)-retinoate
PW_C002690
4HRetA
3263
2
78800
132
122559
124
125132
118
126707
299
128297
388
2706
4-oxo-Retinoic acid
HMDB0006285
4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545).
38030-57-8
C16678
6437063
269971
4941652
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H26O3
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
GGCUJPCCTQNTJF-FRCNGJHJSA-N
314.4186
314.188194698
DBMET00455
FDB023877
4-keto-retinoate;4-keto-retinoic acid;4-ketoretinoate;4-ketoretinoic acid;4-oxo-all-trans-retinoate;4-oxo-all-trans-retinoic acid;4-oxoretinoate;4-oxoretinoic acid;4-oxotretinoin;All-trans-4-oxoretinoate;All-trans-4-oxoretinoic acid;Ro 11-4824;Ro 12-4824
PW_C002706
4ORetA
3264
2
78801
132
122560
124
125133
118
126708
299
128298
388
7979
all-trans-18-Hydroxyretinoic acid
HMDB0012452
all-trans-18-Hydroxyretinoic acid, also known as 18-hydroxy-all-trans-retinoic acid or 18-hydroxyretinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-18-Hydroxyretinoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, all-trans-18-hydroxyretinoic acid is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, all-trans-18-hydroxyretinoic acid is involved in the retinol metabolism pathway. all-trans-18-Hydroxyretinoic acid is also involved in the metabolic disorder called vitamin a deficiency.
C16679
6506224
5005673
C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+
XSJOIRFEYHJNAW-FCKHSPHMSA-N
316.4345
316.203844762
C16679
18-hydroxy-all-trans-retinoate;18-hydroxy-all-trans-retinoic acid;Rac-18-hydroxy-all-trans-retinoate;Rac-18-hydroxy-all-trans-retinoic acid
PW_C007979
AT18HA
3265
2
78802
132
122561
124
125134
118
126709
299
128299
388
7978
all-trans-5,6-Epoxyretinoic acid
HMDB0012451
all-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxyretinoic acid, sodium salt or 5,6-epoxy-5,6-dihydro-retinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-5,6-Epoxyretinoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. all-trans-5,6-Epoxyretinoic acid has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, all-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm and membrane (predicted from logP). In humans, all-trans-5,6-epoxyretinoic acid is involved in the retinol metabolism pathway. all-trans-5,6-Epoxyretinoic acid is also involved in the metabolic disorder called vitamin a deficiency.
C16680
5363137
545933
4515523
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
KEEHJLBAOLGBJZ-WEDZBJJJSA-N
316.4345
316.203844762
DBMET00454
C16680
5,6-epoxy-5,6-dihydro-retinoate;5,6-epoxy-5,6-dihydro-retinoic acid;All-trans-5,6-epoxy-5,6-dihydroretinoate;All-trans-5,6-epoxy-5,6-dihydroretinoic acid;All-trans-5,6-epoxyretinoate
PW_C007978
alt56eA
3266
2
78803
132
25
Fatty Acid
Compound
145
Compound
PW_EC000025
35366
ChEBI
FA
40
Reduced acceptor
Compound
PW_EC000040
15022
ChEBI
RA
41
Acceptor
Compound
PW_EC000041
15339
ChEBI
Accepto
59
Rhodopsin
Compound
PW_EC000059
P08100
UniProt
Rhodops
60
Bathorodopsin
Compound
PW_EC000060
2998
ChEBI
Bathoro
61
iodopsin
Compound
PW_EC000061
5949
ChEBI
Iodopsi
62
Lumirodopsin
Compound
PW_EC000062
6562
ChEBI
Lumirod
63
Metarodopsin
Compound
PW_EC000063
6796
ChEBI
Metarod
729
Alcohol dehydrogenase 1A
P07327
HMDBP00784
ADH1A
4q23
BT019812
1
1.1.1.1
2077
2
3413
8
3611
29
5000
31
143572
26
2201
Retinol dehydrogenase 12
Q96NR8
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. Also involved in the metabolism of short-chain aldehydes. No steroid dehydrogenase activity detected. Might be the key enzyme in the formation of 11-cis-retinal from 11-cis-retinol during regeneration of the cone visual pigments
HMDBP03034
RDH12
14q24.1
CH471061
1
1.1.1.-
3192
2
73
Dehydrogenase/reductase SDR family member 4
Q9BTZ2
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
HMDBP00076
DHRS4
14q11.2
AY358638
1
1.1.1.184
3193
2
2189
Retinol dehydrogenase 16
O75452
Oxidoreductase with a preference for NAD. Oxidizes all- trans-retinol and 13-cis-retinol to the corresponding aldehydes. Has higher activity towards CRBP-bound retinol than with free retinol. Oxidizes 3-alpha-hydroxysteroids. Oxidizes androstanediol and androsterone to dihydrotestosterone and androstanedione. Can also catalyze the reverse reaction
HMDBP03004
RDH16
12q13.3
AF086735
1
1.1.-.-
3194
2
2446
Retinol dehydrogenase 8
Q9NYR8
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity (By similarity).
HMDBP05439
RDH8
19p13.2
AF229845
1
1.1.1.300
3195
2
4107
Short-chain dehydrogenase/reductase 3
O75911
Catalyzes the reduction of all-trans-retinal to all-trans-retinol in the presence of NADPH.
HMDBP08892
DHRS3
1p36.1
AF179237
1
1.1.1.300
3196
2
2015
Dehydrogenase/reductase SDR family member 9
Q9BPW9
3-alpha-hydroxysteroid dehydrogenase that converts 3- alpha-tetrahydroprogesterone (allopregnanolone) to dihydroxyprogesterone and 3-alpha-androstanediol to dihydroxyprogesterone. May play a role in the biosynthesis of retinoic acid from retinaldehyde, but seems to have low activity with retinoids. Can utilize both NADH and NADPH
HMDBP02607
DHRS9
2q31.1
AF343729
1
1.1.-.-
3197
2
2448
Retinol dehydrogenase 11
Q8TC12
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity towards 9-cis and all-trans-retinol. Also involved in the metabolism of short-chain aldehydes. No steroid dehydrogenase activity detected.
HMDBP05442
RDH11
14q24.1
AK289427
1
1.1.1.300
3199
2
137038
18
1676
Lecithin retinol acyltransferase
O95237
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
HMDBP01912
LRAT
4q32.1
AF071510
1
2.3.1.135
3203
2
2520
Acyl-CoA wax alcohol acyltransferase 1
Q58HT5
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
HMDBP07278
AWAT1
Xq13.1
BN000155
1
2.3.1.75
3204
2
237
Diacylglycerol O-acyltransferase 1
O75907
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
HMDBP00243
DGAT1
8q24.3
CH471162
1
2.3.1.20; 2.3.1.76
3205
2
25490
49
1613
Retinoid isomerohydrolase
Q16518
Plays important roles in the production of 11-cis retinal and in visual pigment regeneration. The soluble form binds vitamin A (all-trans-retinol), making it available for LRAT processing to all-trans-retinyl ester. The membrane form, palmitoylated by LRAT, binds all-trans-retinyl esters, making them available for IMH (isomerohydrolase) processing to all-cis-retinol. The soluble form is regenerated by transferring its palmitoyl groups onto 11-cis-retinol, a reaction catalyzed by LRAT. The enzymatic activity is linearly dependent of the expression levels and membrane association.
HMDBP01797
RPE65
1p31
AF039862
1
3.1.1.64
3206
2
2280
Patatin-like phospholipase domain-containing protein 4
P41247
Lipid hydrolase.
HMDBP03160
PNPLA4
Xp22.3
AK304586
1
3.1.1.3
3230
2
1456
Beta,beta-carotene 15,15'-monooxygenase
Q9HAY6
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
HMDBP01568
BCMO1
16q23.2
AF294900
1
1.14.99.36
3234
2
194
Retinal dehydrogenase 1
P00352
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
HMDBP00199
ALDH1A1
9q21.13
M31982
1
1.2.1.36
3244
2
3398
8
3401
7
3758
29
4852
31
143271
1056
200
Retinal dehydrogenase 2
O94788
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
HMDBP00205
ALDH1A2
15q21.3
AC018904
1
1.2.1.36
3245
2
1675
Cytochrome P450 26A1
O43174
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18- hydroxylation. Responsible for generation of several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA and 18-OH-RA
HMDBP01911
CYP26A1
10q23-q24
AK027560
1
1.14.-.-
3248
2
3510
All-trans-retinol 13,14-reductase
Q6NUM9
Retinol saturase carrying out the saturation of the 13-14 double bond of all-trans-retinol to produce all-trans-13,14-dihydroretinol. Has activity toward all-trans-retinol as substrate. Does not use all-trans-retinoic acid nor 9-cis, 11-cis or 13-cis-retinol isomers as substrates. May play a role in the metabolism of vitamin A (By similarity).
HMDBP08290
RETSAT
2p11.2
AY358568
1
1.3.99.23
3250
2
5738
DnaJ homolog subfamily B member 11
Q9UBS4
DNAJB11
AK075430
1
3252
2
3688
29
3868
9
3890
26
4435
31
4450
60
4481
18
4519
10
5181
95
42285
49
135476
1
135687
615
135989
332
141020
847
142933
973
5739
HSP90B1 protein
Q96GW1
HSP90B1
BC009195
1
3253
2
3689
29
3869
9
3891
26
4436
31
4451
60
4482
18
4520
10
5182
95
42286
49
135477
1
135688
615
135990
332
141021
847
142934
973
5740
78 kDa glucose-regulated protein
P11021
HSPA5
AJ271729
1
3254
2
3690
29
3870
9
3892
26
4437
31
4452
60
4483
18
4521
10
5183
95
42287
49
135478
1
135689
615
135991
332
141022
847
142935
973
5741
HYOU1 protein
Q6IN67
HYOU1
BC072436
1
3255
2
3691
29
3871
9
3893
26
4438
31
4453
60
4484
18
4522
10
5184
95
42288
49
135479
1
135690
615
135992
332
141023
847
142936
973
5742
Protein disulfide-isomerase A2
Q13087
PDIA2
U19948
1
5.3.4.1
3256
2
3692
29
3872
9
3894
26
4439
31
4454
60
4485
18
4523
10
5185
95
42289
49
135480
1
135691
615
135993
332
141024
847
142937
973
5743
Protein disulfide-isomerase A4
P13667
PDIA4
BC006344
1
5.3.4.1
3257
2
3693
29
3873
9
3895
26
4440
31
4455
60
4486
18
4524
10
5186
95
42290
49
135481
1
135692
615
135994
332
141025
847
142938
973
5744
Protein disulfide-isomerase A6
Q15084
PDIA6
AK289428
1
5.3.4.1
3258
2
3694
29
3874
9
3896
26
4441
31
4456
60
4487
18
4525
10
5187
95
42291
49
135482
1
135693
615
135995
332
141026
847
142939
973
4776
Peptidyl-prolyl cis-trans isomerase B
P23284
PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides
HMDBP10692
PPIB
15q21-q22
AY962310
1
5.2.1.8
3259
2
3695
29
3875
9
3897
26
4442
31
4457
60
4488
18
4526
10
5188
95
42292
49
135483
1
135694
615
135996
332
141027
847
142940
973
5745
Stromal cell-derived factor 2-like protein 1
Q9HCN8
SDF2L1
CR456570
1
3260
2
3696
29
3876
9
3898
26
4443
31
4458
60
4489
18
4527
10
5189
95
42293
49
135484
1
135695
615
135997
332
141028
847
142941
973
465
UDP-glucuronosyltransferase 1-1
P22309
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
HMDBP00483
UGT1A1
2q37
M84124
1
2.4.1.17
3261
2
3697
29
3877
9
3899
26
4444
31
4459
60
4490
18
4528
10
5190
95
42294
49
135485
1
135696
615
135998
332
141029
847
142942
973
5746
Endoplasmic reticulum resident protein 29
P30040
ERP29
BC101493
1
3262
2
3698
29
3878
9
3900
26
4445
31
4460
60
4491
18
4529
10
5191
95
42295
49
135486
1
135697
615
135999
332
141030
847
142943
973
1455
Cytochrome P450 2A6
P11509
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
HMDBP01567
CYP2A6
19q13.2
AF326721
1
1.14.13.-
3267
2
3360
29
3819
10
3963
26
4828
9
5175
95
136067
49
139922
298
140211
31
140503
847
142880
996
142886
973
1454
Cytochrome P450 2A7
P20853
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
HMDBP01566
CYP2A7
19q13.2
AC008537
1
1.14.14.1
3268
2
141070
29
141398
847
142881
996
142887
973
145241
10
1444
Cytochrome P450 2A13
Q16696
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
HMDBP01556
CYP2A13
19q13.2
AY513606
1
1.14.14.1
3269
2
141071
29
141399
847
142882
996
142888
973
145242
10
1441
Cytochrome P450 2B6
P20813
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
HMDBP01553
CYP2B6
19q13.2
M29874
1
1.14.13.-
1384
49
3270
2
3357
29
3423
14
3434
10
4580
18
136568
36
140212
31
140217
392
140960
847
142682
973
142883
996
1445
Cytochrome P450 3A7
P24462
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
HMDBP01557
CYP3A7
7q21-q22.1
CH236956
1
1.14.14.1
3271
2
3565
29
3737
26
4734
10
141049
69
141064
847
142699
973
142884
996
145251
1321
145429
1399
956
Cytochrome P450 3A4
P08684
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
HMDBP01018
CYP3A4
7q21.1
M18907
1
1.14.13.-; 1.14.13.157; 1.14.13.32; 1.14.13.67; 1.14.13.97
2933
29
3272
2
3290
10
3368
26
4045
31
4577
18
5174
95
135698
615
136000
332
136017
49
136018
331
139914
300
139919
298
140218
325
140451
847
140803
7
140842
844
140845
11
140956
608
141045
69
141080
392
141116
65
142591
996
142689
973
143401
1121
144545
1281
145248
1321
145426
1399
1442
Cytochrome P450 3A5
P20815
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
HMDBP01554
CYP3A5
7q21.1
CH236956
1
1.14.14.1
2934
29
3273
2
3369
26
3436
10
4044
31
4590
18
43395
49
135699
615
136001
332
140804
7
140843
844
140846
11
140959
847
141048
69
141081
392
142613
996
142698
973
144546
1281
145250
1321
145428
1399
1434
Cytochrome P450 3A43
Q9HB55
Exhibits low testosterone 6-beta-hydroxylase activity.
HMDBP01546
CYP3A43
7q21.1
AY390426
1
1.14.14.1
3274
2
3566
29
141400
847
142885
996
142889
973
145243
10
145249
1321
145427
1399
544
Alcohol dehydrogenase 1A
1
PW_P000544
576
729
2
265
9795
4
788
Retinol dehydrogenase 12
1
PW_P000788
893
2201
1
338
143
1
789
Dehydrogenase/reductase SDR family member 4
1
PW_P000789
894
73
1
790
Retinol dehydrogenase 16
1
PW_P000790
895
2189
1
339
721
1
791
Retinol dehydrogenase 8
1
PW_P000791
896
2446
1
792
Short-chain dehydrogenase/reductase 3
1
PW_P000792
897
4107
1
793
Dehydrogenase/reductase SDR family member 9
1
PW_P000793
898
2015
1
340
143
1
341
721
1
794
Retinol dehydrogenase 11
1
PW_P000794
899
2448
1
795
Lecithin retinol acyltransferase
1
PW_P000795
900
1676
1
796
Acyl-CoA wax alcohol acyltransferase 1
1
PW_P000796
901
2520
1
797
Diacylglycerol O-acyltransferase 1
1
PW_P000797
902
237
1
798
Retinoid isomerohydrolase
1
PW_P000798
903
1613
1
342
544
1
800
Patatin-like phospholipase domain-containing protein 4
1
PW_P000800
905
2280
1
801
Beta,beta-carotene 15,15'-monooxygenase
1
PW_P000801
906
1456
1
343
544
1
803
Retinal dehydrogenase 1
1
PW_P000803
908
194
4
804
Retinal dehydrogenase 2
1
PW_P000804
909
200
1
805
Cytochrome P450 26A1
1
PW_P000805
910
1675
1
345
1799
1
806
All-trans-retinol 13,14-reductase
1
PW_P000806
911
3510
1
346
721
1
807
UDP-glucuronosyltransferase 1-1
1
PW_P000807
912
5738
1
913
5739
1
914
5740
1
915
5741
1
916
5742
1
917
5743
1
918
5744
1
919
4776
1
920
5745
1
921
465
1
922
5746
1
808
Cytochrome P450
1
PW_P000808
923
1455
1
924
1454
1
925
1444
1
926
1441
1
927
1445
1
928
956
1
929
1442
1
930
1434
1
347
1799
1
1674
false
PW_R001674
Right
6365
1448
1
Compound
false
6366
721
1
Compound
true
6367
1048
1
Compound
false
6368
1144
1
Compound
true
1411
544
1.1.1.1
1675
false
PW_R001675
Right
6369
1448
1
Compound
false
6370
1048
1
Compound
false
1412
788
1.1.1.-
1676
false
PW_R001676
Right
6371
1448
1
Compound
false
6372
143
1
Compound
true
6373
1048
1
Compound
false
6374
146
1
Compound
true
1413
789
1.1.1.184
1677
false
PW_R001677
Right
6375
1448
1
Compound
false
6376
1048
1
Compound
false
1414
790
1.1.-.-
1678
false
PW_R001678
Right
6377
1448
1
Compound
false
6378
143
1
Compound
true
6379
1048
1
Compound
false
6380
146
1
Compound
true
1415
791
1.1.1.300
1679
false
PW_R001679
Right
6381
1448
1
Compound
false
6382
143
1
Compound
true
6383
1048
1
Compound
false
6384
146
1
Compound
true
1416
792
1.1.1.300
1680
false
PW_R001680
Right
6385
1448
1
Compound
false
6386
1048
1
Compound
false
1417
793
1.1.-.-
1681
false
PW_R001681
Right
6387
1448
1
Compound
false
6388
143
1
Compound
true
6389
2665
1
Compound
false
6390
146
1
Compound
true
1418
794
1.1.1.300
1683
false
PW_R001683
Right
6395
2665
1
Compound
false
6396
4838
1
Compound
false
6397
1948
1
Compound
false
6398
59
1
Compound
true
1420
795
2.3.1.135
1684
false
PW_R001684
Right
6399
2665
1
Compound
false
6400
940
1
Compound
true
6401
1948
1
Compound
false
6402
1099
1
Compound
true
1421
796
2.3.1.75
1685
false
PW_R001685
Right
6403
2665
1
Compound
false
6404
940
1
Compound
true
6405
1948
1
Compound
false
6406
1099
1
Compound
true
1422
797
1687
false
PW_R001687
Right
6411
1935
1
Compound
false
6412
1420
1
Compound
true
6413
2665
1
Compound
false
6414
25
1
ElementCollection
true
1424
798
3.1.1.64
1688
false
PW_R001688
Right
6415
209
1
Compound
false
6416
940
1
Compound
true
6417
1935
1
Compound
false
6418
1099
1
Compound
true
1425
797
1689
false
PW_R001689
Right
6419
209
1
Compound
false
6420
940
1
Compound
true
6421
1935
1
Compound
false
6422
1099
1
Compound
true
1426
796
2.3.1.75
1690
false
PW_R001690
Right
6423
209
1
Compound
false
6424
4838
1
Compound
false
6425
1935
1
Compound
false
6426
59
1
Compound
true
1427
795
2.3.1.135
1691
false
PW_R001691
Right
6427
209
1
Compound
false
6428
143
1
Compound
true
6429
1048
1
Compound
false
6430
146
1
Compound
true
1428
794
1.1.1.300
1692
false
PW_R001692
Right
6431
1935
1
Compound
false
6432
3195
1
Compound
false
6433
209
1
Compound
false
6434
29134
1
Compound
false
1429
800
3.1.1.3
1693
PW_R001693
Right
6435
209
1
Compound
false
6436
2666
1
Compound
false
1694
false
PW_R001694
Right
6437
437
1
Compound
false
6438
1065
1
Compound
true
6439
1048
1
Compound
false
1430
801
1.14.99.36
1695
false
PW_R001695
Right
6440
2666
1
Compound
false
6441
143
1
Compound
true
6442
2667
1
Compound
false
6443
146
1
Compound
true
1431
794
1.1.1.300
1697
false
PW_R001697
Both
6446
2666
1
Compound
false
6447
143
1
Compound
true
6448
2667
1
Compound
false
6449
146
1
Compound
true
1433
794
1.1.1.300
1698
false
PW_R001698
Both
6450
2666
1
Compound
false
6451
143
1
Compound
true
6452
2667
1
Compound
false
6453
146
1
Compound
true
1434
789
1.1.1.184
1699
false
PW_R001699
Right
6454
2667
1
Compound
false
6455
721
1
Compound
true
6456
1420
1
Compound
true
6457
1600
1
Compound
false
6458
1144
1
Compound
true
1435
803
1.2.1.36
1700
false
PW_R001700
Right
6459
2667
1
Compound
false
6460
721
1
Compound
true
6461
1420
1
Compound
true
6462
1600
1
Compound
false
6463
1144
1
Compound
true
1436
804
1.2.1.36
1701
false
PW_R001701
Right
6464
209
1
Compound
false
6465
721
1
Compound
true
6466
1420
1
Compound
true
6467
1227
1
Compound
false
6468
1144
1
Compound
true
1437
803
1.2.1.36
1702
false
PW_R001702
Right
6469
209
1
Compound
false
6470
721
1
Compound
true
6471
1420
1
Compound
true
6472
1227
1
Compound
false
6473
1144
1
Compound
true
1438
804
1.2.1.36
1703
PW_R001703
Right
6474
1227
1
Compound
false
6475
1600
1
Compound
false
1704
false
PW_R001704
Right
6476
209
1
Compound
false
6477
7859
1
Compound
false
1439
805
1.14.-.-
1705
false
PW_R001705
Right
6478
209
1
Compound
false
6479
40
1
ElementCollection
true
6480
7207
1
Compound
false
6481
41
1
ElementCollection
true
1440
806
1.3.99.23
1706
false
PW_R001706
Right
6482
1227
1
Compound
false
6483
40
1
ElementCollection
true
6484
1786
1
Compound
false
6485
41
1
ElementCollection
true
1441
807
5.3.4.1
1707
false
PW_R001707
Right
6486
1227
1
Compound
false
6487
2690
1
Compound
false
1442
805
1.14.-.-
1708
false
PW_R001708
Right
6488
2690
1
Compound
false
6489
2706
1
Compound
false
1443
805
1.14.-.-
1709
false
PW_R001709
Right
6490
1227
1
Compound
false
6491
7979
1
Compound
false
1444
805
1.14.-.-
1710
false
PW_R001710
Right
6492
1227
1
Compound
false
6493
7978
1
Compound
false
1445
808
1.14.13.-
1711
PW_R001711
Right
6494
1448
1
Compound
false
6495
59
1
ElementCollection
false
1712
PW_R001712
Right
6496
59
1
ElementCollection
false
6497
60
1
ElementCollection
false
1713
PW_R001713
Right
6498
59
1
ElementCollection
false
6499
61
1
ElementCollection
false
1714
PW_R001714
Right
6500
61
1
ElementCollection
false
6501
1448
1
Compound
false
1715
PW_R001715
Right
6502
60
1
ElementCollection
false
6503
62
1
ElementCollection
false
1716
PW_R001716
Right
6504
62
1
ElementCollection
false
6505
63
1
ElementCollection
false
1717
PW_R001717
Right
6506
63
1
ElementCollection
false
6507
1048
1
Compound
false
6387
1448
2
81
false
580
740
10
regular
200
190
6388
721
2
59
false
780
440
10
regular
50
30
6389
1048
2
81
false
1125
740
10
regular
200
190
6390
1144
2
60
false
1055
435
10
regular
50
30
6391
9795
2
9
false
900
465
10
regular
100
25
6392
143
2
9
false
912
585
10
regular
100
25
6393
143
2
61
false
815
730
10
regular
50
30
6394
146
2
62
false
1045
735
10
regular
50
30
6395
721
2
9
false
905
925
10
regular
100
25
6396
143
2
61
false
785
1050
10
regular
50
30
6397
146
2
62
false
1090
1050
10
regular
50
30
6398
143
2
61
false
785
1150
10
regular
50
30
6399
146
2
62
false
1090
1150
10
regular
50
30
6400
143
2
9
false
900
1310
10
regular
100
25
6401
721
2
9
false
895
1235
10
regular
100
25
6402
143
2
61
false
560
1010
10
regular
50
30
6403
2665
2
81
false
620
1285
10
regular
200
190
6404
146
2
62
false
560
1210
10
regular
50
30
6409
4838
2
81
false
1075
1485
10
regular
200
190
6410
1948
2
82
false
565
1960
10
regular
300
280
6411
59
2
81
false
1075
1800
10
regular
200
190
6412
940
2
81
false
175
1495
10
regular
200
190
6413
1099
2
85
false
325
1835
10
regular
50
30
6414
940
2
81
false
475
1495
10
regular
200
190
6415
1099
2
85
false
610
1835
10
regular
50
30
6420
1935
2
81
false
1465
1285
10
regular
200
190
6421
1420
2
49
false
1355
1255
10
regular
78
78
6422
544
2
9
false
1205
1335
10
regular
100
25
6447
209
2
81
false
2280
1285
10
regular
200
190
6448
940
2
81
false
2030
975
10
regular
200
190
6449
1099
2
85
false
1835
1140
10
regular
50
30
6463
940
2
3
false
2070
1240
10
regular
100
100
6464
1099
2
85
false
1850
1305
10
regular
50
30
6467
4838
2
81
false
2025
1565
10
regular
200
190
6468
59
2
81
false
1760
1565
10
regular
200
190
6470
143
2
61
false
2065
765
10
regular
50
30
6471
146
2
62
false
1795
770
10
regular
50
30
6481
3195
2
81
false
1535
1780
10
regular
200
190
6482
29134
2
81
false
2255
1785
10
regular
200
190
6483
2666
2
81
false
2275
755
10
regular
200
190
6485
437
2
81
false
1218
265
10
regular
200
190
6486
1065
2
65
false
1374
461
10
regular
78
78
6487
544
2
9
false
1273
550
20
regular
100
25
6488
143
2
61
false
2645
705
10
regular
50
30
6489
2667
2
81
false
2275
295
10
regular
200
190
6490
146
2
62
false
2650
530
10
regular
50
30
6494
143
2
61
false
2270
695
10
regular
50
30
6495
146
2
62
false
2275
530
10
regular
50
30
6499
143
2
61
false
2000
695
10
regular
50
30
6500
146
2
62
false
2005
515
10
regular
50
30
6501
721
2
59
false
2640
465
10
regular
50
30
6502
1420
2
49
false
2560
310
10
regular
78
78
6503
1600
2
81
false
3045
285
10
regular
200
190
6504
1144
2
60
false
2890
465
10
regular
50
30
6505
721
2
59
false
2645
335
10
regular
50
30
6506
1420
2
49
false
2560
175
10
regular
78
78
6507
1144
2
60
false
2895
335
10
regular
50
30
6508
721
2
59
false
2585
1290
10
regular
50
30
6509
1420
2
49
false
2575
1425
10
regular
78
78
6510
1227
2
81
false
2980
1285
10
regular
200
190
6511
1144
2
60
false
2845
1290
10
regular
50
30
6512
721
2
59
false
2510
1540
10
regular
50
30
6513
1420
2
49
false
2550
1595
10
regular
78
78
6514
1144
2
60
false
2915
1545
10
regular
50
30
6515
7859
2
81
false
2475
2095
10
regular
200
190
6516
1799
2
9
false
2540
1875
19
regular
100
25
6517
7207
2
81
false
2705
2095
10
regular
200
190
6518
721
2
9
false
2755
1882
19
regular
100
25
6519
1786
2
81
false
2985
1865
10
regular
200
190
6520
2690
2
81
false
3590
1075
10
regular
200
190
6521
1799
2
9
false
3390
1120
10
regular
100
25
6522
2706
2
81
false
4090
1075
10
regular
200
190
6523
1799
2
9
false
3885
1125
10
regular
100
25
6524
7979
2
81
false
3590
1275
10
regular
200
200
6525
1799
2
9
false
3390
1330
10
regular
100
25
6526
7978
2
81
false
3830
1405
10
regular
200
200
6527
1799
2
9
false
3360
1460
10
regular
100
25
161
25
37
2
false
1100
1245
12
regular
100
90
162
40
37
2
false
2880
1760
12
regular
100
90
163
41
37
2
false
2875
1985
12
regular
100
90
164
40
37
2
false
3170
1495
12
regular
100
90
165
41
37
2
false
3175
1665
12
regular
100
90
166
59
37
false
305
785
12
regular
100
90
167
60
37
false
305
295
12
regular
100
90
168
61
37
false
435
560
12
regular
100
90
169
62
37
false
655
295
12
regular
100
90
172
63
37
false
910
295
12
regular
100
90
2661
729
2
6
false
875
470
8
subunit
regular
160
80
2664
2201
2
2
false
882
600
8
subunit
regular
150
70
2665
73
2
8
false
882
795
8
subunit
regular
140
85
2666
2189
2
2
false
885
940
8
subunit
regular
150
70
2667
2446
2
2
false
885
1030
8
subunit
regular
150
70
2668
4107
2
2
false
885
1130
8
subunit
regular
150
70
2669
2015
2
2
false
875
1250
8
subunit
regular
150
70
2670
2448
18
2
false
585
1095
8
subunit
regular
150
70
2673
1676
2
2
false
930
1707
8
subunit
regular
150
70
2674
2520
2
2
false
365
1712
8
subunit
regular
150
70
2675
237
2
2
false
640
1712
8
subunit
regular
150
70
2679
1613
2
2
false
1185
1345
8
subunit
regular
150
70
2697
237
2
2
false
1925
1180
8
subunit
regular
150
70
2702
2520
2
2
false
1925
1345
8
subunit
regular
150
70
2707
1676
2
2
false
1925
1480
8
subunit
regular
150
70
2709
2448
2
2
false
1885
800
8
subunit
regular
150
70
2716
2280
2
2
false
1920
1845
8
subunit
regular
150
70
2719
1456
2
2
false
1243
565
8
subunit
regular
150
70
2720
2448
2
2
false
2525
590
8
subunit
regular
150
70
2722
2448
2
2
false
2300
595
8
subunit
regular
150
70
2727
73
2
8
false
2040
585
8
subunit
regular
140
85
2728
194
2
8
false
2720
390
8
subunit
regular
140
85
2729
200
2
2
false
2722
265
8
subunit
regular
150
70
2730
194
2
2
false
2675
1345
8
subunit
regular
150
70
2731
200
2
2
false
2675
1525
8
subunit
regular
150
70
2732
1675
2
2
false
2505
1880
8
subunit
regular
150
70
2733
3510
2
2
false
2730
1897
8
subunit
regular
150
70
2734
5738
2
116
false
3010
1622
8
none
regular
160
80
2735
5739
2
124
false
2970
1602
8
none
regular
170
90
2736
5740
2
2
false
2980
1572
8
none
regular
150
70
2737
5741
2
119
false
2980
1617
8
none
regular
160
80
2738
5742
2
116
false
2980
1597
8
none
regular
160
80
2739
5743
2
124
false
2985
1572
8
none
regular
170
90
2740
5744
2
2
false
3020
1562
8
none
regular
150
70
2741
4776
2
119
false
3010
1542
8
none
regular
160
80
2742
5745
2
98
false
3000
1577
8
none
regular
150
70
2743
465
2
97
false
2990
1582
8
none
regular
150
70
2744
5746
2
2
false
3005
1592
8
protein
regular
150
70
2745
1675
2
2
false
3360
1135
8
subunit
regular
150
70
2746
1675
2
2
false
3860
1135
8
subunit
regular
150
70
2747
1675
2
2
false
3370
1340
8
subunit
regular
150
70
2748
1455
2
119
false
3375
1465
8
none
regular
160
80
2749
1454
2
116
false
3370
1440
8
none
regular
160
80
2750
1444
2
113
false
3355
1470
8
none
regular
160
80
2751
1441
2
2
false
3345
1455
8
none
regular
150
70
2752
1445
2
119
false
3375
1465
8
none
regular
160
80
2753
956
2
116
false
3355
1470
8
none
regular
160
80
2754
1442
2
124
false
3340
1450
8
none
regular
170
90
2755
1434
2
2
false
3340
1475
8
protein
regular
150
70
2371
544
109
2
2650
2661
1055
6391
9698
Cofactor
2374
788
109
2
2653
2664
1056
6392
9705
Cofactor
2375
789
109
2
2654
2665
2376
790
109
2
2655
2666
1057
6395
9712
Cofactor
2377
791
109
2
2656
2667
2378
792
109
2
2657
2668
2379
793
109
2
2658
2669
1058
6400
9723
Cofactor
1059
6401
9724
Cofactor
2380
794
109
2
2659
2670
2383
795
109
2
2662
2673
2384
796
109
2
2663
2674
2385
797
109
2
2664
2675
2388
798
109
2
2668
2679
1061
6422
9759
Cofactor
2400
797
109
2
2686
2697
2404
796
109
2
2691
2702
2407
795
109
2
2696
2707
2409
794
109
2
2698
2709
2414
800
109
2
2705
2716
2416
801
109
2
2708
2719
1062
6487
9854
Cofactor
2417
794
109
2
2709
2720
2419
794
109
2
2711
2722
2424
789
109
2
2716
2727
2425
803
109
2
2717
2728
2426
804
109
2
2718
2729
2427
803
109
2
2719
2730
2428
804
109
2
2720
2731
2429
805
109
2
2721
2732
1064
6516
9902
Cofactor
2430
806
109
2
2722
2733
1065
6518
9905
Cofactor
2431
807
109
2
2723
2734
2724
2735
2725
2736
2726
2737
2727
2738
2728
2739
2729
2740
2730
2741
2731
2742
2732
2743
2733
2744
2432
805
109
2
2734
2745
1066
6521
9914
Cofactor
2433
805
109
2
2735
2746
1067
6523
9917
Cofactor
2434
805
109
2
2736
2747
1068
6525
9920
Cofactor
2435
808
109
2
2737
2748
2738
2749
2739
2750
2740
2751
2741
2752
2742
2753
2743
2754
2744
2755
1069
6527
9923
Cofactor
9694
M680 740 C688 643 750 510 875 510
5
false
18
true
M 573.593124483032 631.4371114392959 L 580 645 L 588.5423682837832 632.6700387630692
false
9695
M805 470 C804 507 845 510 875 510
5
false
18
9696
M1225 740 C1223 655 1151 505 1035 510
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9697
M1080 465 C1081 508 1065 510 1035 510
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9698
M425 310 L425 360 L475 310 z
10
true
18
9703
M733 740 C732 651 852 635 882 635
5
false
18
9704
M1174 737 C1174 667 1062 635 1032 635
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9705
M250 250 L250 300 L300 250 z
10
true
18
9706
M780 835 C810 835 852 835 882 835
5
false
18
9707
M840 760 C836 791 852 835 882 835
5
false
18
9708
M1125 835 C1095 835 1052 835 1022 835
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9709
M1070 765 C1073 807 1052 835 1022 835
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9710
M781 901 C812 933 855 975 885 975
5
false
18
9711
M1132 899 C1106 940 1065 975 1035 975
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9712
M250 250 L250 300 L300 250 z
10
true
18
9713
M774 931 C784 967 855 1065 885 1065
5
false
18
9714
M835 1065 C865 1065 855 1065 885 1065
5
false
18
9715
M1137 925 C1143 982 1065 1065 1035 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9716
M1090 1065 C1060 1065 1065 1065 1035 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9717
M722 931 C749 1073 829 1161 885 1165
5
false
18
9718
M835 1165 C865 1165 855 1165 885 1165
5
false
18
9719
M1193 931 C1181 1125 1065 1165 1035 1165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9720
M1090 1165 C1060 1165 1065 1165 1035 1165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9721
M680 930 C716 1120 814 1285 875 1285
5
false
18
9722
M1225 930 C1240 1118 1084 1288 1025 1285
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9723
M250 250 L250 300 L300 250 z
10
true
18
9724
M250 250 L250 300 L300 250 z
10
true
18
9725
M658 930 C658 960 660 1065 660 1095
5
false
18
9726
M610 1025 C658 1025 660 1065 660 1095
5
false
18
9727
M720 1285 C720 1255 660 1195 660 1165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9728
M610 1225 C636 1227 660 1195 660 1165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9737
M820 1380 C931 1380 1005 1677 1005 1707
5
false
18
9738
M1005 1707 C1005 1665 1003 1581 1075 1580
5
false
18
9739
M865 2100 C995 2099 1005 1807 1005 1777
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9740
M1075 1895 C1013 1896 1005 1807 1005 1777
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9741
M620 1380 C470 1381 438 1617 440 1712
5
false
18
9742
M375 1590 C430 1589 440 1663 440 1712
5
false
18
9743
M565 2100 C461 2101 441 1882 440 1782
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9744
M375 1850 C415 1848 440 1812 440 1782
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9745
M720 1475 C720 1505 715 1682 715 1712
5
false
18
9746
M675 1590 C719 1591 715 1682 715 1712
5
false
18
9747
M715 1960 C715 1930 715 1812 715 1782
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9748
M660 1850 C691 1848 715 1812 715 1782
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9756
M1465 1380 C1435 1380 1365 1380 1335 1380
5
false
18
9757
M1394 1333 C1394 1371 1365 1380 1335 1380
5
false
18
9758
M820 1380 C850 1380 1155 1380 1185 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9759
M250 250 L250 300 L300 250 z
10
true
18
9760
M1150 1345 C1149 1377 1155 1380 1185 1380
5
false
18
true
M 1060.9164556685216 1255.2874192894624 L 1050 1245 L 1046.5490613902043 1259.5976375729576
false
9795
M2380 1285 C2374 1220 2105 1215 2075 1215
5
false
18
9796
M2130 1165 C2131 1202 2105 1215 2075 1215
5
false
18
9797
M1565 1285 C1570 1217 1895 1215 1925 1215
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9798
M1860 1170 C1861 1197 1895 1215 1925 1215
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9813
M2280 1380 C2250 1380 2105 1380 2075 1380
5
false
18
9814
M2120 1340 C2121 1368 2105 1380 2075 1380
5
false
18
9815
M1665 1380 C1695 1380 1895 1380 1925 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9816
M1875 1335 C1876 1367 1895 1380 1925 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9821
M2279 1462 C2255 1507 2105 1515 2075 1515
5
false
18
9822
M2125 1565 C2123 1521 2105 1515 2075 1515
5
false
18
9823
M1661 1454 C1717 1518 1895 1515 1925 1515
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9824
M1860 1565 C1860 1533 1895 1515 1925 1515
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9827
M2380 1285 C2359 910 2133 835 2035 835
5
false
18
9828
M2090 795 C2092 821 2065 835 2035 835
5
false
18
9829
M1325 835 C1355 835 1855 835 1885 835
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9830
M1820 800 C1819 832 1855 835 1885 835
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9843
M1565 1475 C1627 1719 1851 1880 1920 1880
5
false
18
9844
M1735 1875 C1765 1875 1890 1880 1920 1880
5
false
18
9845
M2380 1475 C2395 1737 2144 1881 2070 1880
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9846
M2255 1880 C2225 1880 2100 1880 2070 1880
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9847
M2380 1285 C2380 1255 2306 1193 2330 1210
5
true
18
9848
M2375 945 C2374 1079 2370 1179 2380 1285
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9851
M1318 455 C1318 485 1318 535 1318 565
5
false
18
9852
M1374 500 C1333 504 1318 535 1318 565
5
false
18
9853
M1318 739 C1318 709 1318 665 1318 635
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9854
M1393 715 L1393 765 L1443 715 z
10
true
18
9855
M2476 800 C2560 769 2600 690 2600 660
5
false
18
true
M 2520.590284247219 688.466290793611 L 2511 700 L 2525.783627296205 702.538575184411
false
9856
M2645 720 C2621 722 2600 690 2600 660
5
false
18
true
M 2661.3278098408605 601.1701876999267 L 2675 595 L 2662.8203656261753 586.2446298467769
false
9857
M2475 458 C2544 482 2600 560 2600 590
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9858
M2650 545 C2620 546 2600 560 2600 590
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9862
M2375 755 C2375 725 2375 695 2375 665
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9863
M2320 710 C2351 708 2375 695 2375 665
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9864
M2375 485 C2375 515 2375 565 2375 595
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9865
M2325 545 C2371 546 2374 574 2375 595
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9874
M2275 850 C2178 835 2110 700 2110 670
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9875
M2050 710 C2074 710 2110 700 2110 670
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9876
M2275 390 C2197 395 2110 555 2110 585
5
false
18
true
M 2297.5160111000605 248.31564917166372 L 2310 240 L 2296.5564421184104 233.34637305792145
false
9877
M2055 530 C2090 531 2110 555 2110 585
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9878
M2473 427 C2503 427 2690 430 2720 430
5
false
18
9879
M2665 465 C2664 439 2690 430 2720 430
5
false
18
9880
M2599 388 C2597 429 2691 428 2720 430
5
false
18
9881
M3049 433 C3019 433 2890 430 2860 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9882
M2915 465 C2918 430 2890 430 2860 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9883
M2469 300 C2527 299 2692 300 2722 300
5
false
18
9884
M2670 335 C2662 314 2692 300 2722 300
5
false
18
9885
M2599 253 C2594 294 2680 301 2722 300
5
false
18
9886
M3046 300 C3007 301 2902 300 2872 300
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9887
M2920 335 C2924 303 2902 300 2872 300
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9888
M2480 1380 C2510 1380 2645 1380 2675 1380
5
false
18
9889
M2610 1320 C2610 1368 2645 1380 2675 1380
5
false
18
9890
M2614 1425 C2615 1389 2645 1380 2675 1380
5
false
18
9891
M2980 1380 C2950 1380 2855 1380 2825 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9892
M2870 1320 C2872 1366 2855 1380 2825 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9893
M2471 1474 C2524 1519 2645 1560 2675 1560
5
false
18
9894
M2560 1555 C2590 1555 2645 1560 2675 1560
5
false
18
9895
M2589 1595 C2589 1565 2645 1560 2675 1560
5
false
18
9896
M2985 1471 C2937 1521 2855 1560 2825 1560
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9897
M2915 1560 C2885 1560 2855 1560 2825 1560
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9898
M3080 1285 C3080 1255 3006 818 3030 835
5
true
18
9899
M3145 475 C3145 505 3150 1231 3149 1287
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9900
M2405 1468 C2396 1589 2572 1761 2580 1880
5
false
18
9901
M2575 2095 C2575 2065 2580 1980 2580 1950
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9902
M250 250 L250 300 L300 250 z
10
true
18
9903
M2432 1474 C2506 1822 2802 1746 2805 1897
5
false
18
9904
M2805 2095 C2805 2065 2805 1997 2805 1967
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9905
M250 250 L250 300 L300 250 z
10
true
18
9906
M2880 1815 C2821 1818 2805 1867 2805 1897
5
false
18
9907
M2875 2035 C2827 2031 2805 1997 2805 1967
5
false
18
true
M 2761.4316497609916 1941.3953007584944 L 2775 1935 L 2762.677331958798 1926.4471143848214
false
9908
M3080 1475 C3080 1505 3080 1562 3080 1592
5
false
18
9909
M3085 1865 C3085 1835 3080 1692 3080 1662
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9910
M3170 1550 C3122 1552 3080 1562 3080 1592
5
false
18
9911
M3175 1715 C3110 1716 3080 1692 3080 1662
5
false
18
true
M 3061.0952245002686 1620.6264747668563 L 3075 1615 L 3063.174942168285 1605.7713485667412
false
9912
M3172 1287 C3200 1194 3330 1170 3360 1170
5
false
18
9913
M3590 1170 C3560 1170 3540 1170 3510 1170
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9914
M250 250 L250 300 L300 250 z
10
true
18
9915
M3790 1170 C3820 1170 3830 1170 3860 1170
5
false
18
9916
M4090 1170 C4060 1170 4040 1170 4010 1170
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9917
M250 250 L250 300 L300 250 z
10
true
18
9918
M3180 1380 C3210 1380 3340 1375 3370 1375
5
false
18
9919
M3590 1375 C3560 1375 3550 1375 3520 1375
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9920
M250 250 L250 300 L300 250 z
10
true
18
9921
M3180 1431 C3234 1488 3310 1510 3340 1510
5
false
18
9922
M3830 1505 C3800 1505 3520 1510 3490 1510
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9923
M3305 1490 L3305 1540 L3355 1490 z
10
true
18
9924
M580 835 C550 835 445 833 405 835
5
false
18
true
M 317.3417711296125 726.4747032084352 L 305 735 L 318.5540091611033 741.4256389301554
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9925
M405 835 C435 835 481 773 505 790
5
true
18
9926
M355 785 C355 755 354 447 355 395
5
false
18
true
M 261.4815918950292 488.5273414426594 L 255 475 L 246.52577461250553 487.3768939593884
false
9927
M355 395 C355 425 331 693 355 710
5
true
18
9928
M111 112 C134 128 174 155 198 172
5
true
18
9929
M435 610 C368 610 354 735 355 785
5
false
18
true
M 392.5 572.9903810567666 L 385 560 L 377.5 572.9903810567666
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9930
M111 112 C134 128 174 155 198 172
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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9931
M535 610 C626 613 681 670 680 740
5
false
18
true
M 482.2175177365858 627.8864401445276 L 489.5 641 L 497.21543483717977 628.1364054295375
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9932
M405 345 C435 345 456 418 480 435
5
true
18
9933
M655 345 C625 345 462 346 405 345
5
false
18
true
M 537.0096189432334 251.5 L 550 244 L 537.0096189432334 236.5
false
9936
M755 345 C785 345 806 328 830 345
5
true
18
9937
M910 345 C880 345 803 343 755 345
5
false
18
true
M 792.0096189432334 252.5 L 805 245 L 792.0096189432334 237.5
false
9938
M1225 740 C1224 670 1199 348 1010 345
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
9939
M1010 345 C1040 345 1043.5 323 1067.5 340
5
true
18
1922
109
1674
2
6783
6387
9694
Left
6784
6388
9695
Left
6785
6389
9696
Right
6786
6390
9697
Right
1844
1411
2371
1924
109
1675
2
6789
6387
9703
Left
6790
6389
9704
Right
1846
1412
2374
1925
109
1676
2
6791
6387
9706
Left
6792
6393
9707
Left
6793
6389
9708
Right
6794
6394
9709
Right
1847
1413
2375
1926
109
1677
2
6795
6387
9710
Left
6796
6389
9711
Right
1848
1414
2376
1927
109
1678
2
6797
6387
9713
Left
6798
6396
9714
Left
6799
6389
9715
Right
6800
6397
9716
Right
1849
1415
2377
1928
109
1679
2
6801
6387
9717
Left
6802
6398
9718
Left
6803
6389
9719
Right
6804
6399
9720
Right
1850
1416
2378
1929
109
1680
2
6805
6387
9721
Left
6806
6389
9722
Right
1851
1417
2379
1930
109
1681
2
6807
6387
9725
Left
6808
6402
9726
Left
6809
6403
9727
Right
6810
6404
9728
Right
1852
1418
2380
1933
109
1683
2
6819
6403
9737
Left
6820
6409
9738
Left
6821
6410
9739
Right
6822
6411
9740
Right
1855
1420
2383
1934
109
1684
2
6823
6403
9741
Left
6824
6412
9742
Left
6825
6410
9743
Right
6826
6413
9744
Right
1856
1421
2384
1935
109
1685
2
6827
6403
9745
Left
6828
6414
9746
Left
6829
6410
9747
Right
6830
6415
9748
Right
1857
1422
2385
1937
109
1687
2
6834
6420
9756
Left
6835
6421
9757
Left
6836
6403
9758
Right
165
161
9760
Right
1859
1424
2388
1938
109
1688
2
6837
6447
9795
Left
6838
6448
9796
Left
6839
6420
9797
Right
6840
6449
9798
Right
1860
1425
2400
1939
109
1689
2
6841
6447
9813
Left
6842
6463
9814
Left
6843
6420
9815
Right
6844
6464
9816
Right
1861
1426
2404
1940
109
1690
2
6845
6447
9821
Left
6846
6467
9822
Left
6847
6420
9823
Right
6848
6468
9824
Right
1862
1427
2407
1941
109
1691
2
6849
6447
9827
Left
6850
6470
9828
Left
6851
6389
9829
Right
6852
6471
9830
Right
1863
1428
2409
1942
109
1692
2
6853
6420
9843
Left
6854
6481
9844
Left
6855
6447
9845
Right
6856
6482
9846
Right
1864
1429
2414
1943
109
1693
2
6857
6447
9847
Left
6858
6483
9848
Right
1944
109
1694
2
6859
6485
9851
Left
6860
6486
9852
Left
6861
6389
9853
Right
1865
1430
2416
1945
109
1695
2
6862
6483
9855
Left
6863
6488
9856
Left
6864
6489
9857
Right
6865
6490
9858
Right
1866
1431
2417
1947
109
1697
2
6868
6483
9862
Left
6869
6494
9863
Left
6870
6489
9864
Right
6871
6495
9865
Right
1868
1433
2419
1948
109
1698
2
6872
6483
9874
Left
6873
6499
9875
Left
6874
6489
9876
Right
6875
6500
9877
Right
1869
1434
2424
1949
109
1699
2
6876
6489
9878
Left
6877
6501
9879
Left
6878
6502
9880
Left
6879
6503
9881
Right
6880
6504
9882
Right
1870
1435
2425
1950
109
1700
2
6881
6489
9883
Left
6882
6505
9884
Left
6883
6506
9885
Left
6884
6503
9886
Right
6885
6507
9887
Right
1871
1436
2426
1951
109
1701
2
6886
6447
9888
Left
6887
6508
9889
Left
6888
6509
9890
Left
6889
6510
9891
Right
6890
6511
9892
Right
1872
1437
2427
1952
109
1702
2
6891
6447
9893
Left
6892
6512
9894
Left
6893
6513
9895
Left
6894
6510
9896
Right
6895
6514
9897
Right
1873
1438
2428
1953
109
1703
2
6896
6510
9898
Left
6897
6503
9899
Right
1954
109
1704
2
6898
6447
9900
Left
6899
6515
9901
Right
1874
1439
2429
1955
109
1705
2
6900
6447
9903
Left
6901
6517
9904
Right
166
162
9906
Left
167
163
9907
Right
1875
1440
2430
1956
109
1706
2
6902
6510
9908
Left
6903
6519
9909
Right
168
164
9910
Left
169
165
9911
Right
1876
1441
2431
1957
109
1707
2
6904
6510
9912
Left
6905
6520
9913
Right
1877
1442
2432
1958
109
1708
2
6906
6520
9915
Left
6907
6522
9916
Right
1878
1443
2433
1959
109
1709
2
6908
6510
9918
Left
6909
6524
9919
Right
1879
1444
2434
1960
109
1710
2
6910
6510
9921
Left
6911
6526
9922
Right
1880
1445
2435
1961
109
1711
6912
6387
9924
Left
170
166
9925
Right
1962
109
1712
171
166
9926
Left
172
167
9927
Right
1963
109
1713
173
166
9928
Left
174
168
9929
Right
1964
109
1714
6913
6387
9930
Right
175
168
9931
Left
1965
109
1715
176
167
9932
Left
177
169
9933
Right
1967
109
1716
180
169
9936
Left
181
172
9937
Right
1968
109
1717
6914
6389
9938
Right
182
172
9939
Left
386
66
745
900
1.3
1.3
0
2
3
280
360
387
66
535
975
0.8
0.8
0
2
3
280
360
389
66
850
1260
1.9
1.9
60
2
3
280
360
399
66
1805
1140
1.3
1.3
0
2
3
280
360
401
66
1815
700
0.8
0.8
0
2
3
280
360
406
66
2500
505
0.6
0.6
0
2
3
280
360
412
66
2445
1775
0.8
0.8
0
2
3
280
360
413
66
2915
1480
1.0
1.0
0
2
3
280
360
414
66
3290
1010
0.8
0.8
0
2
3
280
360
415
66
3805
1025
0.8
0.8
0
2
3
280
360
416
66
3290
1290
1.0
1.0
0
2
3
280
360
187437
3330
240
2.8
2.8
0
2
14
327
267
479807
3415
1962
1.0
1.0
-30
2
1
490
240
437
M126 224 C126 174 176 124 226 124 C1453 124 3048 124 4275 124 C4325 124 4375 174 4375 224 C4375 860 4375 1687 4375 2323 C4375 2373 4325 2423 4275 2423 C3048 2423 1453 2423 226 2423 C176 2423 126 2373 126 2323 C126 1687 126 860 126 224
1
true
6
4249.0
2299.0
362
235
hv
460
650
20
1.0
1.0
200
15
363
235
hv
250
470
20
1.0
1.0
200
15
364
235
Intracellular Space
370
170
20
1.3
1.3
200
15
366
235
Endoplasmic Reticulum
465
1765
20
1.0
1.0
200
15