70
Pathway
Sulfate/Sulfite Metabolism
This pathway illustrates the conversion of sulfite to sulfate (via sulfate oxidase) and subsequent generation of adenylylsulfate (APS) via 3'-phosphoadenosine 5'-phosphosulfate synthase 2. APS is converted to phosphoadenylyl-sulfate (PAPS) via adenylylsulfate kinase. APS can also be regenerated from PAPS by 3'(2'), 5'-bisphosphate nucleotidase 1. PAPS is eventually converted to adenosine bisophosphate (PAP) through the action of several different enzymes including aryl sulfotransferase, chondroitin 4-sulfotransferase 13 and estrone sulfotransferase.
The metabolism pathway in question is important for many reasons. Recall, that the sulfite ion is in fact the conjugate base of sulfurous acid. Moreover, this ion is found naturally in one of the worlds most popular beverages, wines. Beyond its natural occurence, sulfite ion had the property of stopping fermentation. As such, the addition of it to products such as wine can be used either as a preservative or to stop the fermentation process at a moment which is of interest. Finally, this preservation property goes beyond merely wines, and finds utility in dried fruits, potatoes, etc.
Metabolic
PW000040
Center
PathwayVisualizationContext40
1600
2700
#000099
PathwayVisualization50
70
Sulfate/Sulfite Metabolism
This pathway illustrates the conversion of sulfite to sulfate (via sulfate oxidase) and subsequent generation of adenylylsulfate (APS) via 3'-phosphoadenosine 5'-phosphosulfate synthase 2. APS is converted to phosphoadenylyl-sulfate (PAPS) via adenylylsulfate kinase. APS can also be regenerated from PAPS by 3'(2'), 5'-bisphosphate nucleotidase 1. PAPS is eventually converted to adenosine bisophosphate (PAP) through the action of several different enzymes including aryl sulfotransferase, chondroitin 4-sulfotransferase 13 and estrone sulfotransferase.
The metabolism pathway in question is important for many reasons. Recall, that the sulfite ion is in fact the conjugate base of sulfurous acid. Moreover, this ion is found naturally in one of the worlds most popular beverages, wines. Beyond its natural occurence, sulfite ion had the property of stopping fermentation. As such, the addition of it to products such as wine can be used either as a preservative or to stop the fermentation process at a moment which is of interest. Finally, this preservation property goes beyond merely wines, and finds utility in dried fruits, potatoes, etc.
Metabolic
1
99
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
70
Pathway
100
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
70
Pathway
279631
8586770
Lester MR: Sulfite sensitivity: significance in human health. J Am Coll Nutr. 1995 Jun;14(3):229-32.
70
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
8
Beta cell
CL:0000639
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
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
157
Acinetobacter baumannii
107673
Prokaryote
5
Cytoplasm
GO:0005737
2
Mitochondrion
GO:0005739
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
10
Cell Membrane
GO:0005886
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
11
Extracellular Space
GO:0005615
3
Mitochondrial Matrix
GO:0005759
18
Melanosome Membrane
GO:0033162
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
12
Mitochondrial Inner Membrane
GO:0005743
25
Golgi Apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
8
Smooth Endoplasmic Reticulum
GO:0005790
27
Peroxisome Membrane
GO:0005778
32
Inner Membrane
GO:0070258
19
Sarcoplasmic Reticulum
GO:0016529
26
Golgi Apparatus Membrane
GO:0000139
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
18
Pancreas
BTO:0000988
5
cardiocyte
BTO:0001539
8
5
1
1
PW_BS000008
3
2
1
1
PW_BS000003
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
122
5
5
1
PW_BS000122
407
2
5
1
PW_BS000115
135
5
17
1
PW_BS000135
119
2
17
1
PW_BS000119
481
2
10
1
PW_BS000115
206
2
6
1
PW_BS000024
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
16
2
1
2
PW_BS000016
18
13
1
1
PW_BS000018
14
10
1
PW_BS000014
28
1
16
1
1
PW_BS000028
10
1
7
1
1
PW_BS000010
31
1
5
1
1
PW_BS000031
20
4
1
1
1
PW_BS000020
15
11
1
PW_BS000015
4
3
1
1
PW_BS000004
33
18
1
1
PW_BS000033
2
1
1
1
PW_BS000002
49
7
1
1
PW_BS000049
24
4
10
1
1
PW_BS000024
22
14
1
1
PW_BS000022
29
1
1
1
PW_BS000029
42
24
1
1
PW_BS000042
13
1
2
1
PW_BS000013
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
108
1
3
PW_BS000108
147
1
24
1
PW_BS000147
159
24
PW_BS000159
188
1
18
PW_BS000024
163
2
18
1
PW_BS000163
160
1
18
1
PW_BS000160
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
151
1
4
1
PW_BS000151
216
4
18
1
PW_BS000024
198
5
18
1
PW_BS000024
215
6
18
1
PW_BS000024
211
10
18
PW_BS000024
225
35
4
1
PW_BS000024
164
4
PW_BS000164
286
36
4
1
PW_BS000024
226
4
4
1
PW_BS000024
249
13
4
1
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
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13
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PW_BS000024
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6
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PW_BS000024
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PW_BS000024
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PW_BS000024
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PW_BS000017
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PW_BS000024
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294
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PW_BS000024
134
12
12
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PW_BS000134
130
13
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PW_BS000130
331
7
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PW_BS000028
332
1
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PW_BS000028
113
6
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PW_BS000113
115
10
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PW_BS000115
334
4
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PW_BS000028
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1
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PW_BS000028
337
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16
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PW_BS000028
129
1
5
12
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PW_BS000129
341
4
1
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PW_BS000028
114
11
12
PW_BS000114
133
3
12
1
PW_BS000133
329
14
12
1
PW_BS000028
132
1
12
1
PW_BS000132
345
24
12
1
PW_BS000028
343
18
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
408
4
5
1
PW_BS000115
405
10
5
PW_BS000115
414
1
5
5
1
PW_BS000115
409
11
5
PW_BS000115
406
3
5
1
PW_BS000115
415
18
5
1
PW_BS000115
124
1
5
1
PW_BS000124
383
7
5
1
PW_BS000100
434
4
10
5
1
PW_BS000115
429
1
5
1
PW_BS000115
382
14
5
1
PW_BS000100
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
376
10
17
PW_BS000053
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
448
1
16
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
137
11
17
PW_BS000137
120
3
17
1
PW_BS000120
451
18
17
1
PW_BS000115
118
1
17
1
PW_BS000118
398
7
17
1
PW_BS000113
469
4
10
17
1
PW_BS000115
464
1
17
1
PW_BS000115
399
14
17
1
PW_BS000113
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
482
4
10
1
PW_BS000115
478
10
10
PW_BS000115
483
11
10
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
299
1
10
1
PW_BS000024
484
14
10
1
PW_BS000115
495
7
10
1
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
502
4
6
1
PW_BS000115
207
6
6
1
PW_BS000024
209
10
6
PW_BS000024
208
11
6
PW_BS000024
205
5
6
1
PW_BS000024
501
3
6
1
PW_BS000115
504
18
6
1
PW_BS000115
388
1
6
1
PW_BS000112
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
395
13
6
1
PW_BS000113
390
7
6
1
PW_BS000112
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
54
1
3
1
5
PW_BS000054
43
25
1
1
PW_BS000043
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
70
28
5
1
1
PW_BS000070
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
94
3
PW_BS000094
103
3
3
1
PW_BS000103
105
11
3
PW_BS000105
110
2
3
1
PW_BS000110
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
101
5
3
1
PW_BS000101
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
107
31
3
PW_BS000107
95
1
7
2
1
PW_BS000095
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
1
1
PW_BS000001
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
117
1
3
1
PW_BS000117
214
25
18
1
PW_BS000024
222
3
4
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
170
18
PW_BS000170
162
12
18
1
PW_BS000162
26
1
1
1
5
PW_BS000026
277
1
2
18
PW_BS000024
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
65
11
1
PW_BS000065
290
5
49
1
PW_BS000024
308
10
1
1
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
253
5
4
1
PW_BS000024
333
1
2
12
PW_BS000028
347
1
3
12
5
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
356
25
12
1
PW_BS000028
368
3
60
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
425
1
3
5
5
PW_BS000115
419
25
5
1
PW_BS000115
436
25
5
PW_BS000115
446
1
2
17
PW_BS000115
460
1
3
17
5
PW_BS000115
455
25
17
1
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
507
25
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
790
6
11
1
PW_BS000524
834
6
1
1
1
PW_BS000549
185
3
2
1
PW_BS000024
187
31
18
PW_BS000024
51
8
1
PW_BS000051
326
8
12
PW_BS000028
416
8
5
PW_BS000115
452
8
17
PW_BS000115
488
8
10
PW_BS000115
505
8
6
PW_BS000115
11
1
8
1
1
PW_BS000011
141
1
7
19
1
PW_BS000141
78
8
1
1
PW_BS000078
32
1
15
1
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PW_BS000032
39
7
1
1
3
PW_BS000039
58
1
14
1
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PW_BS000058
59
27
1
1
PW_BS000059
66
18
5
1
8
PW_BS000066
23
15
1
1
PW_BS000023
91
8
5
1
1
PW_BS000091
89
2
PW_BS000089
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
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PW_BS000024
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
335
27
12
1
PW_BS000028
184
1
2
1
PW_BS000024
109
32
3
PW_BS000109
433
1
14
5
1
PW_BS000115
410
15
5
1
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
468
1
14
17
1
PW_BS000115
444
15
17
1
PW_BS000115
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
485
15
10
1
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
516
15
6
1
PW_BS000115
508
27
6
1
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517
15
6
PW_BS000115
891
14
2
1
PW_BS000552
288
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4
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PW_BS000024
306
35
51
1
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372
10
2
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47
19
1
4
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313
23
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241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
304
1
2
PW_BS000024
21
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4
PW_BS000021
56
26
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PW_BS000056
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157
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162
Sulfite
HMDB0000240
Endogenous sulfite is generated as a consequence of the body's normal processing of sulfur-containing amino acids. Sulfites occur as a consequence of fermentation and also occur naturally in a number of foods and beverages. As food additives, sulfiting agents were first used in 1664 and have been approved in the United States since the 1800s. Sulfite is an allergen, a neurotoxin, and a metabotoxin. An allergen is a compound that causes allergic reactions such as wheezing, rash, or rhinitis. A neurotoxin is a substance that causes damage to nerves or brain tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. As an allergen, sulfite is known to induce asthmatic reactions. Sulfite sensitivity occurs most often in asthmatic adults (predominantly women), but it is also occasionally reported in preschool children. Adverse reactions to sulfites in nonasthmatics are extremely rare. Asthmatics who are steroid-dependent or who have a higher degree of airway hyperreactivity may be at greater risk of experiencing a reaction to sulfite-containing foods. Sulfite sensitivity reactions vary widely, ranging from no reaction to severe. The majority of reactions are mild. These manifestations may include dermatologic, respiratory, or gastrointestinal signs and symptoms. The precise mechanisms of the sensitivity responses have not been completely elucidated: inhalation of sulfur dioxide (SO2) generated in the stomach following ingestion of sulfite-containing foods or beverages, a deficiency in a mitochondrial enzyme, and an IgE-mediated immune response have all been implicated. Exogenously supplied sulfite is detoxified by the enzyme sulfite oxidase. Sulfite oxidase (EC 1.8.3.1) is 1 of 3 enzymes in humans that require molybdenum as a cofactor. Under certain circumstances, chronically high levels of sulfite can lead to serious neurotoxicity. Sulfite oxidase deficiency (also called molybdenum cofactor deficiency) is a rare autosomal inherited disease that is typified by high concentrations of sulfite in the blood and urine. It is characterized by severe neurological symptoms such as untreatable seizures, attenuated growth of the brain, and mental retardation. It results from defects in the enzyme sulfite oxidase, which is responsible for the oxidation of sulfite to sulfate. This sulfite to sulfate reaction is the final step in the degradation of sulfur-containing metabolites (including the amino acids cysteine and methionine). The term "isolated sulfite oxidase deficiency" is used to define the deficiency caused by mutations in the sulfite oxidase gene. This differentiates it from another version of sulfite oxidase deficiency that is due to defects in the molybdenum cofactor biosynthetic pathway (with mutations in the MOCS1 or MOCS2 genes). Isolated sulfite oxidase deficiency is a rare but devastating neurologic disease that usually presents in early infancy with seizures and alterations in muscle tone (PMID: 16234925, 16140720, 8586770). Sulfite oxidase deficiency (as caused by MOCS1 or MOCS2) may be treated with cPMP, a precursor of the molybdenum cofactor (PMID: 20385644). The mechanism behind sulfite neurotoxicity appears to be related to its ability to bind and inhibit glutamate dehydrogenase (GDH). Inhibition of GDH leads to a decrease in alpha-ketoglutarate and a diminished flux through the tricarboxylic acid cycle. This is accompanied by a decrease in NADH through the mitochondrial electron transport chain, which leads to a decrease in mitochondrial membrane potential and in ATP synthesis. Since glutamate is a major metabolite in the brain, inhibition of GDH by sulfite appears to contribute to neural damage characteristic of sulfite oxidase deficiency in human infants (PMID: 15273247).
14265-45-3
C00094
1099
17359
SO3
1068
OS(O)=O
H2O3S
InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)
LSNNMFCWUKXFEE-UHFFFAOYSA-N
sulfurous acid
82.079
81.97246462
2
sulfurous acid
0
-1
FDB021915
Bisulfite;Sulfite dianion;Sulfite ion;Sulfite ions;Sulfonate;Sulfur trioxide;Sulfuric anhydride;Sulphite;Trioxosulfate(2-);Trioxosulfate(iv);Trioxosulphate(2-);Trioxosulphate(iv);[so3](2-);So3(2-);Sulphite ion
PW_C000162
Sulfite
713
8
1241
3
77784
111
79000
112
120563
122
120952
407
123197
135
123518
119
125893
481
127354
206
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
dioxygen
31.9988
31.989829244
0
singlet oxygen
0
0
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
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
water
18.0153
18.010564686
1
water
0
0
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
1118
Sulfate
HMDB0001448
The sulfate ion is a polyatomic anion with the empirical formula SO42- and a molecular mass of 96.06 daltons; it consists of one central sulfur atom surrounded by four equivalent oxygen atoms in a tetrahedral arrangement. The sulfate ion carries a negative two charge and is the conjugate base of the hydrogen sulfate ion, HSO4-, which is the conjugate base of H2SO4, sulfuric acid. In inorganic chemistry, a sulfate (IUPAC-recommended spelling; also sulphate in British English) is a salt of sulfuric acid. Sulfate aerosols can act as cloud condensation nuclei and this leads to greater numbers of smaller droplets of water. Lots of smaller droplets can diffuse light more efficiently than just a few larger droplets.
14808-79-8
C00059
1117
16189
NH42SO4
1085
OS(O)(=O)=O
H2O4S
InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)
QAOWNCQODCNURD-UHFFFAOYSA-N
sulfuric acid
98.078
97.967379242
2
sulfuric acid
0
-2
FDB022629
Sulfate (ion 2-);Sulfate anion;Sulfate anion(2-);Sulfate dianion;Sulfate ion;Sulfate ion (so42-);Sulfate(2-);Sulfuric acid ion(2-);Sulphate;[so4](2-);So4(2-);Sulphate ion;Sulfuric acid;Sulphuric acid;Sulfuric acid anion(2-);Sulphate anion(2-);Sulphuric acid anion(2-);Sulfuric acid dianion;Sulphate dianion;Sulphuric acid dianion;Sulfuric acid ion;Sulphuric acid ion;Sulfuric acid(2-);Sulphate(2-);Sulphuric acid(2-);Sulfate ion(2-);Sulphate ion(2-);Sulphuric acid ion(2-)
PW_C001118
SO4
1242
3
2209
9
4883
49
6268
108
6269
107
7254
215
7353
188
7355
187
42470
318
42471
315
77205
225
77388
331
78891
113
79001
112
120953
407
122110
126
122352
383
123519
119
124661
443
124905
398
125894
481
126264
301
126532
495
127355
206
127828
207
128104
390
1783
Hydrogen peroxide
HMDB0003125
Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).
7722-84-1
C00027
784
16240
HYDROGEN-PEROXIDE
763
OO
H2O2
InChI=1S/H2O2/c1-2/h1-2H
MHAJPDPJQMAIIY-UHFFFAOYSA-N
peroxol
34.0147
34.005479308
2
hydrogen peroxide
0
0
FDB014562
Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;Hooh
PW_C001783
H2O2
98
9
113
5
188
8
551
14
627
28
755
15
1243
3
1691
2
1749
51
2534
22
3818
10
4749
13
4752
31
5495
126
5502
123
5510
127
5810
108
6005
147
7038
163
8396
151
11817
216
11886
215
12461
226
12709
291
12719
292
13028
301
13035
298
13040
302
13405
222
42658
315
77022
225
77047
294
77079
293
77500
113
77540
334
77598
115
77720
332
77725
337
77806
114
77810
111
77819
326
78073
329
78152
132
78598
112
120050
408
120102
122
120463
405
120595
409
120609
416
120954
407
121047
124
122120
382
122801
374
122814
443
122839
135
123097
376
123157
447
123165
448
123220
137
123234
452
123520
119
123611
118
124672
399
125428
482
125469
297
125709
478
125732
483
125748
488
125895
481
126103
299
126275
484
126967
502
126978
207
127006
205
127201
209
127215
208
127230
505
127356
206
127601
388
127838
389
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
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
616.487
616.177297665
-5.48
2
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
0
-2
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
1004
Molybdenum
HMDB0001302
Molybdenum is a transition metal with the atomic symbol Mo, atomic number 42, and atomic weight 95.94. The pure metal is silvery white in color, fairly soft, and has one of the highest melting points of all pure elements. Physiologically, it exists as an ion in the body. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase. There is a trace requirement for molybdenum in plants, and soils can be barren due to molybdenum deficiencies. Plants and animals generally have molybdenum present in amounts of a few parts per million. In animals molybdenum is a cofactor of the enzyme xanthine oxidase which is involved in the pathways of purine degradation and formation of uric acid. In some animals, adding a small amount of dietary molybdenum enhances growth. Francis Crick suggested that since molybdenum is an essential trace element that plays an important role in many enzymatic reactions, despite being less abundant than the more common elements, such as chromium and nickel, that perhaps this fact is indicative of "Panspermia." Crick theorized that if it could be shown that the elements represented in terrestrial living organisms correlate closely with those that are abundant in some class of star - molybdenum stars, for example, that this would provide evidence of such Directed Panspermia. In small quantities, molybdenum is effective at hardening steel. Molybdenum is important in plant nutrition, and is found in certain enzymes, including xanthine oxidase. Molybdenum is used to this day in high-strength alloys and in high-temperature steels. Special molybdenum-containing alloys, such as the Hastelloys, are notably heat-resistant and corrosion-resistant. Molybdenum is used in oil pipelines, aircraft and missile parts, and in filaments. Molybdenum finds use as a catalyst in the petroleum industry, especially in catalysts for removing organic sulfurs from petroleum products. It is used to form the anode in some x-ray tubes, particularly in mammography applications. And is found in some electronic applications as the conductive metal layers in thin-film transistors (TFTs). Molybdenum disulfide is a good lubricant, especially at high temperatures. And Mo-99 is used in the nuclear isotope industry. Molybdenum pigments range from red-yellow to a bright red orange and are used in paints, inks, plastics, and rubber compounds.
7439-98-7
C00150
185498
28685
CPD-8123
161267
[Mo++]
Mo
InChI=1S/Mo/q+2
MMVYPOCJESWGTC-UHFFFAOYSA-N
molybdenum(2+) ion
95.94
97.905407846
0
molybdenum(2+) ion
2
2
FDB003653
Mo;Molybdaen;Molybdene;Molybdenum atom;Molybdenum elemental;Molybdenum insoluble compounds;Molybdenum metallic
PW_C001004
MolyBDN
1245
3
79002
112
120956
407
123522
119
125897
481
127358
206
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
140770
891
793
Adenosine phosphosulfate
HMDB0001003
Adenosine phosphosulfate (also known as APS) is the initial compound formed by the action of ATP sulfurylase (or PAPS synthetase) on sulfate ions after sulfate uptake. PAPS synthetase 1 is a bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway.
485-84-7
C00224
10238
17709
APS
9821
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O
C10H14N5O10PS
InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
IRLPACMLTUPBCL-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
427.284
427.019898895
-2.11
5
adenosine phosphosulfate
0
-2
FDB022362
Amps;Aps;Adenosine 5'-phosphosulfate;Adenosine 5'-sulphatophosphate;Adenosine phosphosulfate;Adenosine sulfatophosphate;Adenylic acid monoanhydride with sulfurate;Adenylic acid monoanhydride with sulfuric acid;Adenylyl sulfate;Adenylyl-sulfate;Phosphosulfate;Sulfatophosphate;Adenosine 5'-phosphosulphate;Adenosine phosphosulphate;Adenylyl sulphate;Adenylyl-sulphate;Phosphosulphate;Adenosine-5'-phosphosulfate;Adenylylsulfate;Adenosine 5'-phosphosulfuric acid;Adenosine 5'-phosphosulphuric acid
PW_C000793
APS
1247
8
77206
225
79003
111
120958
122
123524
135
125899
297
127360
205
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
OP(O)(=O)OP(O)(O)=O
H4O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)
XPPKVPWEQAFLFU-UHFFFAOYSA-N
(phosphonooxy)phosphonic acid
177.9751
177.943225506
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
140772
891
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
886
Phosphoadenosine phosphosulfate
HMDB0001134
3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.
482-67-7
C00053
10214
17980
PAPS
9799
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O
C10H15N5O13P2S
InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1
GACDQMDRPRGCTN-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
507.264
506.986229305
-2.00
6
3'-phosphoadenylyl sulfate
0
-4
FDB022445
3'-phospho-5'-adenylyl sulfate;3'-phosphoadenosine 5'-phosphosulfate;3'-phosphoadenosine-5'-phosphosulfate;3'-phosphoadenylyl sulfate;3'-phosphoadenylyl-sulfate;5-phosphoadenosine 3-phosphosulfate;Paps;Phosphoadenosine phosphosulfate;3'-phospho-5'-adenylyl sulphate;3'-phosphoadenosine 5'-phosphosulphate;3'-phosphoadenosine-5'-phosphosulphate;3'-phosphoadenylyl sulphate;3'-phosphoadenylyl-sulphate;5-phosphoadenosine 3-phosphosulphate;Phosphoadenosine phosphosulphate;3'-phosphoadenosine 5'-phosphosulfuric acid;3'-phosphoadenosine 5'-phosphosulphuric acid
PW_C000886
Paps
1249
8
2205
43
4585
18
4893
31
5198
97
5843
143
7251
214
8436
151
43376
2
77346
111
78887
356
79983
132
120960
122
122106
419
122699
124
123525
135
124657
455
125286
118
125900
297
126261
490
126837
299
127361
205
127825
507
128444
388
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
OP(O)(O)=O
H3O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)
NBIIXXVUZAFLBC-UHFFFAOYSA-N
phosphoric acid
97.9952
97.976895096
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
140773
891
94
Estrone
HMDB0000145
Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961, 17513923, 17470679, 17464097).
53-16-7
C00468
5870
17263
ESTRONE
5660
DB00655
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
C18H22O2
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
DNXHEGUUPJUMQT-CBZIJGRNSA-N
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
270.3661
270.161979948
-4.84
1
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
0
0
DBMET00490
FDB012798
(+)-estrone;1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-17-keto-estra-1,3,5-triene;3-hydroxyestra-1,3,5(10)-trien-17-one;3-hydroxyestra-1,3,5(10)-triene-17-one;3-hydroxyoestra-1,3,5(10)-trien-17-one;D1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-1,3,5(10)-estratrien-17-one;Follicular hormone;Folliculin;Oestrone
PW_C000094
Estrone
340
8
1401
2
42298
49
77345
111
79927
331
79982
132
120962
122
122685
383
122698
124
123527
135
125271
398
125285
118
125902
297
126820
495
126836
299
127363
205
128425
390
128443
388
43
Adenosine 3',5'-diphosphate
HMDB0000061
Adenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy.
1053-73-2
C00054
159296
17985
3-5-ADP
140102
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
WHTCPDAXWFLDIH-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
427.2011
427.029414749
-2.11
6
adenosine 3',5'-bisphosphate
0
-4
FDB021887
3'-phosphoryl-amp;3,5-adp;3,5-diphosphoadenosine;3-phosphoadenosine 5-phosphate;5-(dihydrogen phosphate) 3-adenylate;5-(dihydrogen phosphate)3'-adenylic acid;Adenosine 3',5'-bisphosphate;Adenosine 3,5-bis;Adenosine 3,5-bisphosphate;3'-phosphoadenylate;Pap;Phosphoadenosine phosphate;3'-phosphoadenylic acid;Adenosine 3',5'-bismonophosphoric acid;Adenosine 3',5'-bisphosphoric acid;Phosphoadenosine phosphoric acid
PW_C000043
A3'5'PP
1251
8
2207
43
4587
18
4895
31
5200
97
5845
143
7253
214
8437
151
43377
2
77348
111
78889
356
79985
132
120963
122
122108
419
122701
124
123528
135
124659
455
125288
118
125903
297
126263
490
126839
299
127364
205
127827
507
128446
388
1101
Estrone sulfate
HMDB0001425
Estrone sulfate is a sulfated estrone derivative. Estrone sulfate acts as a long-lived reservoir that can be converted as needed to the more active estradiol (from estrone via 17 beta-hydroxysteroid dehydrogenase). Estrone Sulfate (E1S) is the most abundant circulating estrogen in non-pregnant women as well as normal men. Estrone is primarily synthesized from estrone sulfate. Estrone is an estrogenic hormone secreted by the ovaries and adipose tissues. Estrone is one of the three estrogens found in humans. The other two are estriol and estradiol. Estrone is the least prevalent of the three. Estradiol plays a critical role on reproductive and sexual functioning in women and it also affects other organs including the bones. Estriol is an estrogen that is prevalent primarily during pregnancy.
481-97-0
C02538
3001028
17474
ESTRONE-SULFATE
2272513
DB04574
C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O
C18H22O5S
InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1
JKKFKPJIXZFSSB-CBZIJGRNSA-N
[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
350.429
350.118794504
-4.77
1
Ogen
0
-1
DBMET00530
FDB021804
Conestoral;Estrogenic substances;Estrone;Estrone hydrogen sulfate;Estrone 3-sulfate;Estrone sulfate;Estrone sulfate sodium;Estrone-3-sulfate;Premarin;Sodium estrone 3-monosulfate;Sodium estrone 3-sulfate;Estrone hydrogen sulphate;Estrone 3-sulphate;Estrone sulphate;Estrone sulphate sodium;Estrone-3-sulphate;Sodium estrone 3-monosulphate;Sodium estrone 3-sulphate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphate;Estrone hydrogen sulfate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfate;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfuric acid;3-hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphuric acid;Estrone 3-sulfuric acid;Estrone 3-sulphuric acid;Estrone hydrogen sulfuric acid;Estrone hydrogen sulphate;Estrone hydrogen sulphuric acid;Estrone sulfuric acid;Estrone sulphuric acid
PW_C001101
Estrone
341
8
1402
2
77347
111
79984
132
120964
122
122700
124
123529
135
125287
118
125904
297
126838
299
127365
205
128445
388
153
Phenol
HMDB0000228
Phenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2].
108-95-2
C00146
20488062
15882
24-DICHLOROPHENOL
971
DB03255
OC1=CC=CC=C1
C6H6O
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
phenol
94.1112
94.041864814
-0.31
1
phenol
0
0
FDB000893
Acide carbolique;Anbesol;Benzenol;Benzophenol;Campho-phenique cold sore gel;Campho-phenique gel;Campho-phenique liquid;Carbolic acid;Carbolic acid liquid;Carbolic oil;Carbolicum acidum;Carbolsaure;Cepastat lozenges;Cuticura pain relieving ointment;Fenol;Fenolo;Fenosmolin;Fenosmoline;Hydroxy-benzene;Hydroxybenzene;Iph;Izal;Liquefied phenol;Liquid phenol;Liquified phenol;Monohydroxy benzene;Monohydroxybenzene;Monophenol;Oxybenzene;Phoh;Paoscle;Phenic;Phenic acid;Phenic alcohol;Phenol;Phenol alcohol;Phenol homopolymer;Phenol liquid;Phenol molten;Phenol polymer-bound;Phenol solution;Phenol synthetic;Phenolated water;Phenolated water for disinfection;Phenole;Phenosmolin;Phenylic acid;Phenylic alcohol;Synthetic phenol;Tea polyphenol;Phenol for disinfection;Phenol, liquefied
PW_C000153
Phenol
1256
8
79005
111
120966
122
123531
135
125906
297
127367
205
40399
Phenol sulphate
HMDB0060015
Phenol sulphate, also known as phenylsulfate or aryl sulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Phenol sulphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Phenol sulphate has been detected in multiple biofluids, such as feces and urine. Within the cell, phenol sulphate is primarily located in the cytoplasm. Phenol sulphate exists in all living organisms, ranging from bacteria to humans. In humans, phenol sulphate is involved in the sulfate/sulfite metabolism pathway. Phenol sulphate is also involved in the metabolic disorder called sulfite oxidase deficiency. Phenol sulphate belongs to the family of Substituted Benzenes. These are aromatic compounds containing a benzene substituted at one or more positions.
937-34-8
C00850
74426
27905
67018
OS(=O)(=O)OC1=CC=CC=C1
C6H6O4S
InChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
CTYRPMDGLDAWRQ-UHFFFAOYSA-N
phenyloxidanesulfonic acid
174.174
173.99867937
-1.69
1
phenylsulfate
0
-1
Phenyl hydrogen sulfate;Phenylsulfate;Aryl sulfate;Sulfuric acid, monophenyl ester;Phenyl hydrogen sulphate;Phenylsulphate;Aryl sulphate;Phenol sulfate;Phenol sulfuric acid;Phenol sulphuric acid;Phenylsulfuric acid;Phenylsulphuric acid
PW_C040399
PheSul
1257
8
79006
111
120967
122
123532
135
125907
297
127368
205
655
Propyl alcohol
HMDB0000820
Propyl alcohol is a colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate. Propyl alcohol is a primary alcohol with the formula CH3CH2CH2OH. It is also known as propan-1-ol, 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes and small amounts are produced by gut microflora.
71-23-8
C05979
1031
28831
PROPANOL
1004
DB03175
CCCO
C3H8O
InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
BDERNNFJNOPAEC-UHFFFAOYSA-N
propan-1-ol
60.095
60.057514878
0.81
1
propanol
0
0
FDB008280
1-hydroxypropane;1-propanol;1-propyl alcohol;Ethylcarbinol;Hydroxypropane;N-propan-1-ol;N-propanol;Optal;Propan-1-ol;Propane-1-ol;Propanol;Propanol-1;Propanole;Propanolen;Propyl alcohol;Propylan-propyl alcohol;Propylic alcohol;N-propyl alcohol;Osmosol extra;Un 1274
PW_C000655
Propyol
4700
2
79007
132
120969
124
123534
118
125909
299
127369
388
40706
Propyl sulfate
HMDB0061375
Sulfuric acid, monopropyl ester, also known as sulphate, monopropyl ester, belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group). Sulfuric acid, monopropyl ester is soluble (in water) and an extremely strong acidic compound (based on its pKa).
70469
63647
CCCOS(O)(=O)=O
C3H8O4S
InChI=1S/C3H8O4S/c1-2-3-7-8(4,5)6/h2-3H2,1H3,(H,4,5,6)
TYRGSDXYMNTMML-UHFFFAOYSA-N
propoxysulfonic acid
140.158
140.014329434
-0.86
1
propoxysulfonic acid
0
-1
PW_C040706
PropS
4701
2
79008
132
120970
124
123535
118
125910
299
127370
388
489
Chondroitin
HMDB0000629
Chondroitin is a mucopolysaccharide constituent of chondrin. Chondrin is a gelatin-like protein-carbohydrate substance that can be obtained by boiling cartilage in water. Cartilage is a connective tissue that contains cells embedded in a matrix of chondrin. Chondroitin is a glycosaminoglycan (GAG) composed of a chain of alternating sugars (N-acetyl-galactosamine and glucuronic acid). It is usually found attached to proteins as part of a proteoglycan. A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. The structure depicted in this MetaboCard is simply a disaccharide component of the chontroitin subunit. Chondroitin's functions largely depend on the properties of the overall proteoglycan of which it is a part. These functions can be broadly divided into structural and regulatory roles. However, this division is not absolute and some proteoglycans have both structural and regulatory roles. Chondroitin is an ingredient found commonly in dietary supplements used as an alternative medicine to treat osteoarthritis. It is commonly sold together with glucosamine. The dosage of oral chondroitin used in human clinical trials is 800-1200 mg per day. Most chondroitin appears to be made from extracts of cartilaginous cow and pig tissues (cow trachea and pig ear and nose), but other sources such as shark, fish and bird cartilage are also used. Since chondroitin is not a uniform substance, and is naturally present in a wide variety of forms, the precise composition of each supplement will vary. While it is a prescription or over-the-counter drug in 22 countries, chondroitin is regulated in the U.S. as a food product by the Food and Drug Administration. As a result, there are no mandatory standards for formulation, and no guarantee that the product is correctly labelled.
9007-27-6
C00401
53477707
16137
[H]O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O
(C14H21NO11)nH2O
InChI=1S/C14H23NO12/c1-3(17)15-5-10(6(18)4(2-16)25-13(5)24)26-14-9(21)7(19)8(20)11(27-14)12(22)23/h4-11,13-14,16,18-21,24H,2H2,1H3,(H,15,17)(H,22,23)/t4-,5-,6+,7+,8+,9-,10-,11+,13-,14-/m1/s1
LJORHONFMDUUHP-YHCGEDBISA-N
-0.53
0
FDB022150
(2r,3r,4s)-2-[(2r,3r,4r,5r,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4-dihydroxy-3,4-dihydro-2h-pyran-6-carboxylic acid;4-deoxy-l-threo-hex-4-enopyranosyluronic acid-(1,3)-n-acetyl-d-galactosamine;Chondroitin disaccharide;Chondroitin-d-glucuronate;Unsaturated chondroitin disaccharide
PW_C000489
Chondro
1253
8
4703
2
79009
132
120972
124
123537
118
125912
299
127372
388
510
Chondroitin 4-sulfate
HMDB0000652
Chondroitin 4-sulfate is a derivative of chondroitin which has a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate. An example structure is given, and this Chondroiton sulfate is a polymer that can contain up to 100 individual sugars.
C00634
70678574
37397
CHONDROITIN-4-SULFATE
30776543
[H]O[C@@H]1O[C@H](CO)[C@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O
(C14H21NO14S)nH2O
InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1
AVJBPWGFOQAPRH-MMPMEFKSSA-N
-0.81
0
FDB022163
Chondroitin 4'-sulfate;Chondroitin sulfate a;Chondroitin 4'-sulphate;Chondroitin sulphate a
PW_C000510
C4S
1254
8
4704
2
79010
132
120973
124
123538
118
125913
299
127373
388
994
Sulfite oxidase, mitochondrial
P51687
HMDBP01057
SUOX
12q13.2
AY056018
1
1.8.3.1
1246
3
346
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2
O95340
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. May have a important role in skeletogenesis during postnatal growth (By similarity).
HMDBP00353
PAPSS2
10q24
AF160503
1
2.7.7.4; 2.7.1.25
1248
8
336
3'(2'),5'-bisphosphate nucleotidase 1
O95861
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6.
HMDBP00342
BPNT1
1q41
AK291943
1
3.1.3.7
1250
8
339
Estrogen sulfotransferase
P49888
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
HMDBP00346
SULT1E1
4q13.1
U20515
1
2.8.2.4
1252
8
3914
26
4897
31
5202
97
43378
2
335
Sulfotransferase 1A1
P50225
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
HMDBP00341
SULT1A1
16p12.1
U54701
1
2.8.2.1
1258
8
3912
26
4272
2
4588
18
4896
31
5201
97
141981
913
348
Sulfotransferase family cytosolic 2B member 1
O00204
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
HMDBP00355
SULT2B1
19q13.3
AC008403
1
2.8.2.2
306
11
1259
8
4702
2
280
Carbohydrate sulfotransferase 11
Q9NPF2
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
HMDBP00286
CHST11
12q
AJ269537
1
2.8.2.5
1255
8
4705
2
347
Sulfite oxidase, mitochondrial
1
PW_P000347
368
994
2
156
1799
1
157
1004
1
348
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2
1
PW_P000348
369
346
1
349
3'(2'),5'-bisphosphate nucleotidase 1
1
PW_P000349
370
336
1
158
423
1
350
Estrogen sulfotransferase
1
PW_P000350
371
339
2
352
Sulfotransferase 1A1
1
PW_P000352
373
335
2
20
Sulfotransferase family cytosolic 2B member 1
1
PW_P000020
21
348
351
Carbohydrate sulfotransferase 11
1
PW_P000351
372
280
1
858
false
PW_R000858
Both
3472
162
1
Compound
false
3473
1065
1
Compound
true
3474
1420
1
Compound
true
3475
1118
1
Compound
false
3476
1783
1
Compound
true
423
347
1.8.3.1
859
false
PW_R000859
Right
3477
414
1
Compound
true
3478
1118
1
Compound
false
3479
793
1
Compound
false
3480
170
1
Compound
true
424
348
438
false
PW_R000438
Right
1821
414
1
Compound
true
1822
793
1
Compound
false
1823
1034
1
Compound
true
1824
886
1
Compound
false
425
348
180
false
PW_R000180
Right
798
886
1
Compound
false
799
1420
1
Compound
true
800
793
1
Compound
false
801
1104
1
Compound
true
426
349
3.1.3.7
45
false
PW_R000045
Right
172
94
1
Compound
false
4655
886
1
Compound
false
173
1101
1
Compound
false
4656
43
1
Compound
false
929
350
2.8.2.4
527
false
PW_R000527
Right
2201
886
1
Compound
false
2202
153
1
Compound
true
2203
43
1
Compound
false
2204
40399
1
Compound
true
429
352
2.8.2.1
861
false
PW_R000861
Right
3485
886
1
Compound
false
3486
655
1
Compound
true
3487
43
1
Compound
false
3488
40706
1
Compound
true
430
20
2.8.2.2
860
false
PW_R000860
Right
3481
886
1
Compound
false
3482
489
1
Compound
false
3483
43
1
Compound
false
3484
510
1
Compound
false
428
351
2.8.2.5
2023
162
3
81
false
245
350
10
regular
200
190
2024
1065
3
65
false
456
311
10
regular
78
78
2025
1420
3
49
false
465
508
10
regular
78
78
2026
1118
3
81
false
770
350
10
regular
200
190
2027
1783
3
56
false
686
306
10
regular
78
78
2028
1799
3
9
false
570
395
10
regular
100
25
2029
1004
3
9
false
575
475
10
regular
100
25
2033
414
8
42
false
980
355
10
regular
50
30
2034
793
8
81
false
1380
353
10
regular
200
190
2035
170
8
45
false
1223
346
10
regular
63
43
2036
414
8
42
false
1290
653
10
regular
50
30
2037
1034
8
43
false
1295
818
10
regular
50
30
2038
886
8
81
false
1375
933
10
regular
200
200
2042
1420
8
49
false
1610
763
10
regular
78
78
2043
1104
8
46
false
1629
586
10
regular
44
43
2044
423
8
9
false
1500
658
19
regular
100
25
2045
94
8
81
false
1655
1198
10
regular
200
190
2046
43
8
81
false
2300
938
10
regular
200
190
2047
1101
8
81
false
2010
1198
10
regular
200
190
2050
153
8
81
false
1085
1173
10
regular
200
190
2051
43
8
81
false
575
938
10
regular
200
190
2052
40399
8
81
false
765
1178
10
regular
200
190
10084
655
2
81
false
1080
708
10
regular
200
190
10085
40706
2
81
false
795
708
10
regular
200
190
10087
489
2
81
false
1700
728
10
regular
200
190
10088
510
2
81
false
2090
728
10
regular
200
190
770
994
3
6
false
540
405
8
subunit
regular
160
80
772
346
8
2
false
1055
410
8
subunit
regular
150
70
773
346
8
2
false
1330
713
8
subunit
regular
150
70
775
336
8
2
false
1470
668
8
subunit
regular
150
70
776
339
8
6
false
1855
1068
8
subunit
regular
160
80
778
335
8
6
false
940
1063
8
subunit
regular
160
80
5517
348
2
2
false
962
928
8
subunit
regular
150
70
5518
280
2
2
false
1922
948
8
subunit
regular
150
70
720
347
50
3
763
770
308
2028
2935
Cofactor
309
2029
2936
Cofactor
722
348
50
8
765
772
723
348
50
8
766
773
725
349
50
8
768
775
311
2044
2958
Cofactor
726
350
50
8
769
776
728
352
50
8
771
778
4519
20
50
2
5488
5517
4520
351
50
2
5489
5518
2930
M445 445 C475 445 510 445 540 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2931
M495 389 C495 420 510 445 540 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2932
M504 508 C504 477 510 445 540 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2933
M770 445 C740 445 727 445 697 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2934
M725 384 C725 417 730 445 700 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2935
M200 200 L200 250 L250 200 z
10
true
18
2936
M200 200 L200 250 L250 200 z
10
true
18
2941
M1005 385 C1005 422 1025 445 1055 445
5
false
18
2942
M970 445 C1000 445 1025 445 1055 445
5
false
18
2943
M1380 448 C1350 448 1235 445 1205 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2944
M1254.5 389 C1254.5 421 1235 445 1205 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2945
M1340 668 C1371 668 1405 683 1405 713
5
false
18
2946
M1405 545 C1405 575 1405 683 1405 713
5
false
18
2947
M1345 833 C1374 833 1405 813 1405 783
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2948
M1405 931 C1405 901 1405 813 1405 783
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2954
M1545 935 C1545 905 1545 768 1545 738
5
false
18
2955
M1610 802 C1582 801 1545 777 1545 738
5
false
18
2956
M1545 545 C1545 575 1545 638 1545 668
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2957
M1629 607.5 C1592 607.5 1545 622 1545 668
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2958
M200 200 L200 250 L250 200 z
10
true
18
2959
M1576 1108 C1606 1108 1825 1108 1855 1108
5
false
18
2960
M1755 1198 C1755 1163 1784 1108 1855 1108
5
false
18
2961
M2296 1108 C2266 1108 2045 1108 2015 1108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2962
M2110 1198 C2110 1161 2085 1107 2015 1108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2967
M1374 1103 C1344 1103 1130 1103 1100 1103
5
false
18
2968
M1185 1173 C1185 1140 1159 1102 1100 1103
5
false
18
2969
M781 1103 C811 1103 910 1103 940 1103
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2970
M865 1178 C865 1146 879 1104 940 1103
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
15983
M1372 963 C1342 963 1142 963 1112 963
5
false
18
15984
M1180 898 C1175 941 1142 963 1112 963
5
false
18
15985
M780 963 C810 963 932 963 962 963
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
15986
M895 898 C898 937 932 963 962 963
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
15988
M1574 983 C1604 983 1892 983 1922 983
5
false
18
15989
M1800 918 C1802 963 1878 983 1922 983
5
false
18
15990
M2293 981 C2263 981 2102 983 2072 983
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
15991
M2190 918 C2191 970 2128 983 2072 983
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
595
50
858
3
2196
2023
2930
Left
2197
2024
2931
Left
2198
2025
2932
Left
2199
2026
2933
Right
2200
2027
2934
Right
566
423
720
597
50
859
8
2205
2033
2941
Left
2206
2026
2942
Left
2207
2034
2943
Right
2208
2035
2944
Right
568
424
722
598
50
438
8
2209
2036
2945
Left
2210
2034
2946
Left
2211
2037
2947
Right
2212
2038
2948
Right
569
425
723
600
50
180
8
2217
2038
2954
Left
2218
2042
2955
Left
2219
2034
2956
Right
2220
2043
2957
Right
571
426
725
601
50
45
8
2221
2038
2959
Left
2222
2045
2960
Left
2223
2046
2961
Right
2224
2047
2962
Right
572
427
726
603
50
527
8
2229
2038
2967
Left
2230
2050
2968
Left
2231
2051
2969
Right
2232
2052
2970
Right
574
429
728
3032
50
861
2
9631
2038
15983
Left
9632
10084
15984
Left
9633
2051
15985
Right
9634
10085
15986
Right
3071
430
4519
3033
50
860
2
9635
2038
15988
Left
9636
10087
15989
Left
9637
2046
15990
Right
9638
10088
15991
Right
3072
428
4520
95
13
220
255
1.5
1.5
0
2
1
490
240
187175
1670
285
1.6
1.6
0
3
14
327
267
479720
1916
360
1.6
1.6
-35
2
3
280
360
134
M125 224 C125 174 175 124 225 124 C908 124 1795 124 2478 124 C2528 124 2578 174 2578 224 C2578 573 2578 1026 2578 1375 C2578 1425 2528 1475 2478 1475 C1795 1475 908 1475 225 1475 C175 1475 125 1425 125 1375 C125 1026 125 573 125 224
1
true
6
2453.0
1351.0
143
235
Extracellular Space
250
30
20
1.0
1.0
200
15
144
235
Intracellular Space
260
165
20
1.0
1.0
200
15