64
Pathway
Pyruvaldehyde Degradation
This Pyruvaldehyde degradation pathway (Methylglyoxal degradation;2-oxopropanal degradation), also known as the glyoxalase system, is probably the most common pathway for the degradation of pyruvaldehyde (methylglyoxal), a potentially toxic metabolite due to its interaction with nucleic acids and other proteins. Pyruvaldehyde is formed in low concentrations by glycolysis, fatty acid metabolism and protein metabolism. Pyruvaldehyde is catalyzed by the glyoxylase system, composed of the enzymes lactoylglutathione lyase (glyoxalase I) and glyoxylase II. Glyoxalase I catalyes the isomerization of the spontaneously formed hemithioacetal adduct between glutathione and pyruvaldehyde into S-lactoylglutathione. S-lactoylglutathione is then catalyzed by glyoxalase II into D-lactic acid and glutathione. D-lactic acid is then catalyzed by an unknown quinol in the membrane to pyruvic acid, which then enters pyruvate metabolism.
Metabolic
PW000034
Center
PathwayVisualizationContext34
1200
2450
#000099
PathwayVisualization44
64
Pyruvaldehyde Degradation
This Pyruvaldehyde degradation pathway (Methylglyoxal degradation;2-oxopropanal degradation), also known as the glyoxalase system, is probably the most common pathway for the degradation of pyruvaldehyde (methylglyoxal), a potentially toxic metabolite due to its interaction with nucleic acids and other proteins. Pyruvaldehyde is formed in low concentrations by glycolysis, fatty acid metabolism and protein metabolism. Pyruvaldehyde is catalyzed by the glyoxylase system, composed of the enzymes lactoylglutathione lyase (glyoxalase I) and glyoxylase II. Glyoxalase I catalyes the isomerization of the spontaneously formed hemithioacetal adduct between glutathione and pyruvaldehyde into S-lactoylglutathione. S-lactoylglutathione is then catalyzed by glyoxalase II into D-lactic acid and glutathione. D-lactic acid is then catalyzed by an unknown quinol in the membrane to pyruvic acid, which then enters pyruvate metabolism.
Metabolic
1
1
Cell
CL:0000000
2
Platelet
CL:0000233
6
Myocyte
CL:0000187
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
12
Astrocyte
CL:0000127
4
Cardiomyocyte
CL:0000746
7
Epithelial Cell
CL:0000066
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
19
Schizosaccharomyces pombe
4896
Eukaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
3
Escherichia coli
562
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
25
Escherichia coli (strain K12)
83333
Prokaryote
202
Spathaspora passalidarum
340170
Eukaryote
Spathaspora passalidarum
5
Cytoplasm
GO:0005737
10
Cell Membrane
GO:0005886
1
Cytosol
GO:0005829
7
Endoplasmic Reticulum Membrane
GO:0005789
14
Mitochondrial Outer Membrane
GO:0005741
3
Mitochondrial Matrix
GO:0005759
11
Extracellular Space
GO:0005615
4
Peroxisome
GO:0005777
35
Chloroplast
GO:0009507
2
Mitochondrion
GO:0005739
12
Mitochondrial Inner Membrane
GO:0005743
13
Endoplasmic Reticulum
GO:0005783
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
20
Endoplasmic Reticulum Lumen
GO:0005788
39
Mitochondrial membrane
GO:0031966
18
Melanosome Membrane
GO:0033162
25
Golgi Apparatus
GO:0005794
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
2
Endothelium
BTO:0000393
8
Blood Vessel
BTO:0001102
74
11
28
Stomach
BTO:0001307
155
26
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
8
5
1
1
PW_BS000008
111
5
12
1
PW_BS000111
122
5
5
1
PW_BS000122
135
5
17
1
PW_BS000135
297
5
10
1
PW_BS000024
205
5
6
1
PW_BS000024
14
10
1
PW_BS000014
2
1
1
1
PW_BS000002
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1
7
1
1
PW_BS000010
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7
1
1
PW_BS000049
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1
5
1
1
PW_BS000031
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1
5
2
1
PW_BS000097
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19
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PW_BS000143
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1
4
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1
7
12
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PW_BS000115
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17
PW_BS000053
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1
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17
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7
17
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PW_BS000113
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10
10
PW_BS000115
299
1
10
1
PW_BS000024
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10
6
PW_BS000024
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14
1
1
PW_BS000022
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14
12
1
PW_BS000028
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14
5
1
PW_BS000100
399
14
17
1
PW_BS000113
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14
10
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PW_BS000115
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14
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11
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17
PW_BS000137
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PW_BS000115
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3
10
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11
10
PW_BS000115
388
1
6
1
PW_BS000112
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3
6
1
PW_BS000115
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11
6
PW_BS000024
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1
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PW_BS000003
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1
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PW_BS000108
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1
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PW_BS000024
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PW_BS000119
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PW_BS000028
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1
12
5
PW_BS000028
368
3
60
1
PW_BS000028
367
1
60
1
PW_BS000028
94
3
PW_BS000094
121
12
17
1
PW_BS000121
423
9
5
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6
PW_BS000115
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5
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PW_BS000115
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5
17
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PW_BS000115
459
1
1
17
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PW_BS000115
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1
3
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PW_BS000054
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PW_BS000017
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24
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PW_BS000107
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PW_BS000100
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11
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PW_BS000105
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2
24
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PW_BS000157
159
24
PW_BS000159
152
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PW_BS000152
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PW_BS000101
188
1
18
PW_BS000024
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31
18
PW_BS000024
163
2
18
1
PW_BS000163
219
31
4
PW_BS000024
213
7
18
1
PW_BS000024
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13
18
1
PW_BS000024
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1
7
18
1
PW_BS000024
170
18
PW_BS000170
162
12
18
1
PW_BS000162
224
2
4
1
PW_BS000024
195
13
18
PW_BS000024
164
4
PW_BS000164
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
223
12
4
1
PW_BS000024
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
134
12
12
1
PW_BS000134
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
130
13
12
1
PW_BS000130
310
31
2
PW_BS000024
304
1
2
PW_BS000024
390
7
6
1
PW_BS000112
109
32
3
PW_BS000109
425
1
3
5
5
PW_BS000115
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
125
13
5
1
PW_BS000125
460
1
3
17
5
PW_BS000115
454
24
17
1
PW_BS000115
136
13
17
1
PW_BS000136
495
7
10
1
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
882
31
202
PW_BS000552
883
1
202
1
PW_BS000552
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31
1
PW_BS000167
168
32
1
PW_BS000168
788
24
11
1
3
PW_BS000524
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24
1
12
PW_BS000336
185
3
2
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PW_BS000024
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6
1
1
PW_BS000009
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4
1
1
PW_BS000005
28
1
16
1
1
PW_BS000028
58
1
14
1
1
PW_BS000058
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1
20
1
1
PW_BS000036
13
1
2
1
PW_BS000013
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1
3
1
PW_BS000006
102
12
3
1
PW_BS000102
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
179
12
21
1
PW_BS000179
216
4
18
1
PW_BS000024
215
6
18
1
PW_BS000024
211
10
18
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
113
6
12
1
PW_BS000113
334
4
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
358
39
12
PW_BS000028
369
12
60
1
PW_BS000028
408
4
5
1
PW_BS000115
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
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1
16
17
1
PW_BS000115
482
4
10
1
PW_BS000115
502
4
6
1
PW_BS000115
207
6
6
1
PW_BS000024
186
12
2
1
PW_BS000024
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
43
25
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1
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10
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PW_BS000024
60
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1
1
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PW_BS000046
72
5
1
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PW_BS000072
61
25
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PW_BS000061
37
7
21
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25
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27
15
1
PW_BS000027
7
1
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PW_BS000007
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PW_BS000110
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10
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PW_BS000140
146
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PW_BS000146
180
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PW_BS000180
214
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S-Lactoylglutathione
HMDB0001066
S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase (PMID: 8632674). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442).
25138-66-3
C03451
440018
15694
S-LACTOYL-GLUTATHIONE
389032
C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O
C13H21N3O8S
InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1
VDYDCVUWILIYQF-CSMHCCOUSA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid
379.386
379.104935353
-1.70
6
S-lactoylglutathione
0
-1
FDB022405
(r)-s-lactoylglutathione;D-lactoylglutathione;N-(n-l-gamma-glutamyl-s-(2-hydroxy-1-oxopropyl)-l-cysteinyl)-glycine;S-d-lactoyl-glutathione;S-d-lactoylglutathione;S-lactate glutathione;S-lactateglutathione;S-lactoyl-glutathione;S-lactylglutathione;S-[(2r)-2-hydroxypropanoyl]-gamma-l-glutamyl-l-cysteinylglycine;S-delta-lactoyl-glutathione;S-delta-lactoylglutathione;Delta-lactoylglutathione;S-lactoylglutathione
PW_C000841
S-LacGu
1176
8
78758
111
120874
122
123450
135
125850
297
127523
205
80
Glutathione
HMDB0000125
Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. glutathione is also important in red and white blood cell formation and throughout the immune system. glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (http://www.dcnutrition.com/AminoAcids/) glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (http://en.wikipedia.org/wiki/glutathione).
70-18-8
C00051
124886
16856
OXIDIZED-GLUTATHIONE
111188
DB00143
N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
C10H17N3O6S
InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
RWSXRVCMGQZWBV-WDSKDSINSA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
307.323
307.083805981
-2.54
6
glutathione
0
-1
DBMET00487
FDB001498
5-l-glutamyl-l-cysteinylglycine;Agifutol s;Bakezyme rx;Copren;Deltathione;Gsh;Glutathion;Glutathione;Glutathione red;Glutathione reduced;Glutathione-sh;Glutatiol;Glutatione;Glutide;Glutinal;Isethion;L-glutamyl-l-cysteinylglycine;L-glutathione;L-glutathione reduce;L-g-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinyl-glycine;L-gamma-glutamyl-l-cysteinylglycine;Ledac;Neuthion;Red. glutathione;Reduced glutathione;Tathion;Tathione;Triptide;Gamma-glutamylcysteinylglycine;Gamma-l-glutamyl-l-cysteinyl-glycine;Gamma-l-glutamyl-l-cysteinylglycine;N-(n-gamma-l-glutamyl-l-cysteinyl)glycine;G-l-glutamyl-l-cysteinyl-glycine;γ-l-glutamyl-l-cysteinyl-glycine;N-(n-g-l-glutamyl-l-cysteinyl)glycine;N-(n-γ-l-glutamyl-l-cysteinyl)glycine
PW_C000080
GSH
161
14
199
8
614
2
1337
10
1362
49
4889
31
5193
97
5839
143
8426
151
77403
332
77408
111
77424
331
78015
115
78761
132
80709
135
120098
405
120187
122
120880
124
121067
123
121093
383
122838
376
123456
118
123632
447
123658
398
125467
478
125544
297
125856
299
127004
209
127077
205
905
Pyruvaldehyde
HMDB0001167
Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.
78-98-8
C00546
880
17158
METHYL-GLYOXAL
857
DB03587
CC(=O)C=O
C3H4O2
InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
AIJULSRZWUXGPQ-UHFFFAOYSA-N
2-oxopropanal
72.0627
72.021129372
0.40
0
methylglyoxal
0
0
FDB008295
1,2-propanedione;1-ketopropionaldehyde;2-keto propionaldehyde;2-ketopropionaldehyde;2-oxo-propionaldehyde;2-oxopropanal;Acetylformaldehyde;Acetylformyl;Ketopropionaldehyde;Methylglyoxal;Propanedione;Propanolone;Pyroracemic aldehyde;Pyruvaldehyde;Pyruvic aldehyde;Alpha-ketopropionaldehyde;2-oxopropionaldehyde;Ch3cocho;A-ketopropionaldehyde;α-ketopropionaldehyde
PW_C000905
Pyruval
1177
8
2535
22
78074
329
78759
111
120875
122
122121
382
123451
135
124673
399
125851
297
126276
484
127525
205
127839
389
1005
Zinc (II) ion
HMDB0001303
Zinc is an essential element, necessary for sustaining all life.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 types of cells 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. 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 kills some organisms.
23713-49-7
C00038
32051
29105
ZN%2b2
29723
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
FDB003729
Zinc;Zinc ion;Dietary zinc;Zinc cation;Zinc, ion (zn2+);Zn(ii);Zn(2+);Zn2+
PW_C001005
Zinc
13
2
38
4
118
8
271
16
529
15
2957
51
3044
68
3120
29
3147
70
5410
117
5425
103
5434
118
5459
120
5560
132
5585
133
5598
135
7449
166
11787
198
12466
226
12724
290
13321
151
76967
225
77401
111
77580
114
77929
336
80400
1
120020
124
120035
406
120060
122
120441
409
121257
429
123075
137
123827
464
125398
299
125413
479
125438
297
125685
483
126938
388
126953
501
126976
205
127180
208
1010
D-Lactic acid
HMDB0001311
Lactic acid is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. D-Lactic acid is the end product of the enzyme glyoxalase II (or hydroxyacyl-glutathione hydrolase) (EC 3.1.2.6), which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate (OMIM: 138790).
10326-41-7
C00256
61503
42111
D-LACTATE
55423
DB03066
C[C@H](O)C(O)=O
C3H6O3
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
JVTAAEKCZFNVCJ-REOHCLBHSA-N
(2S)-2-hydroxypropanoic acid
90.0779
90.031694058
2
(α)-lactate
0
-1
FDB003293
(-)-lactate;(-)-lactic acid;(r)-(-)-lactate;(r)-(-)-lactic acid;(r)-2-hydroxypropanoate;(r)-2-hydroxypropanoic acid;(r)-2-hydroxypropionate;(r)-2-hydroxypropionic acid;(r)-lactate;(r)-lactic acid;(r)-a-hydroxypropionate;(r)-a-hydroxypropionic acid;(r)-alpha-hydroxypropionate;(r)-alpha-hydroxypropionic acid;D-(-)-lactate;D-(-)-lactic acid;D-2-hydroxypropanoate;D-2-hydroxypropanoic acid;D-2-hydroxypropionate;D-2-hydroxypropionic acid;D-lactate;D-lactic acid;Dla;L-(+)-lactate;L-lactic acid;Propel;Tisulac;Delta-(-)-lactate;Delta-(-)-lactic acid;Delta-2-hydroxypropanoate;Delta-2-hydroxypropanoic acid;Delta-2-hydroxypropionate;Delta-2-hydroxypropionic acid;Delta-lactate;Delta-lactic acid
PW_C001010
D-Lac
1179
8
1744
3
6154
108
6219
166
42700
315
78760
111
78767
112
120877
122
121443
407
123453
135
124001
119
125853
297
126068
481
127521
206
164
Pyruvic acid
HMDB0000243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeure
PW_C000164
Pyr
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
7457
222
7495
220
8200
225
12622
31
15292
249
15349
18
77310
111
77972
346
77978
327
78090
112
80004
368
80042
367
80695
135
112879
94
115683
121
119950
406
120011
124
120175
122
120878
407
121148
423
121154
424
123454
119
123720
458
123726
459
125340
479
125390
299
125534
297
125854
481
126883
501
126931
388
127067
205
127858
206
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
140692
882
140693
883
140699
167
140707
168
140715
14
140742
788
140743
597
140760
185
964
FAD
HMDB0001248
FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
C27H33N9O15P2
InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
VWWQXMAJTJZDQX-UYBVJOGSSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
785.5497
785.157134455
-2.27
9
flavine-adenine dinucleotide
0
-3
FDB022511
1h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;Adeflavin
PW_C000964
FAD
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
7465
222
7487
223
9076
224
11818
216
11887
215
11899
211
12296
225
12328
249
12443
151
12519
227
12595
226
12710
291
12720
292
13029
301
13041
302
43623
318
77080
293
77126
133
77152
134
77501
113
77507
112
77518
115
77541
334
77615
132
77726
337
78054
329
78375
345
78930
331
79222
336
79272
358
80012
368
80034
369
80714
119
119958
406
119999
384
120051
408
120107
407
120432
405
120453
122
120490
124
121278
429
121298
418
121417
382
121489
383
122748
120
122776
121
122802
374
122823
443
123066
376
123087
135
123166
448
123849
464
123868
454
123976
399
124047
398
125348
479
125378
480
125429
482
125474
481
125697
297
125979
489
126107
299
126277
484
126891
501
126920
391
126968
502
126987
207
127011
206
127310
209
127432
506
127602
388
127840
389
140790
185
140799
186
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
17
Ferricytochrome c
ProteinComplex
PW_EC000017
15991
ChEBI
FC
16
Ferrocytochrome c
ProteinComplex
PW_EC000016
16928
ChEBI
FC
384
Lactoylglutathione lyase
Q04760
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B.
HMDBP00392
GLO1
6p21.3-p21.1
AB209801
1
4.4.1.5
1178
8
2358
Probable D-lactate dehydrogenase, mitochondrial
Q86WU2
HMDBP03582
LDHD
16q23.1
BC047902
1
1.1.2.4
1182
3
757
Hydroxyacylglutathione hydrolase, mitochondrial
Q16775
Thiolesterase that catalyzes the hydrolysis of S-D-lactoyl-glutathione to form glutathione and D-lactic acid.
HMDBP00812
HAGH
16p13.3
AK290155
1
3.1.2.6
1180
8
4348
2
324
Lactoylglutathione lyase
1
PW_P000324
345
384
2
144
1005
2
326
Probable D-lactate dehydrogenase, mitochondrial
1
PW_P000326
347
2358
1
146
964
1
480
Hydroxyacylglutathione hydrolase, mitochondrial
1
PW_P000480
503
757
1
231
1005
2
375
false
PW_R000375
Both
1554
841
1
Compound
false
1555
80
1
Compound
false
1556
905
1
Compound
true
395
324
4.4.1.5
844
false
PW_R000844
Both
3421
1010
1
Compound
false
3422
17
2
ElementCollection
true
3423
164
1
Compound
false
3424
16
2
ElementCollection
true
3425
40034
2
Compound
true
397
326
1.1.2.4
288
false
PW_R000288
Right
1213
841
1
Compound
false
1214
1420
1
Compound
true
1215
80
1
Compound
false
1216
1010
1
Compound
false
7821
40034
1
Compound
true
396
480
3.1.2.6
1912
841
8
81
false
845
285
10
regular
200
190
1913
80
8
81
false
245
285
10
regular
200
190
1914
905
8
81
false
410
480
10
regular
200
190
1915
1005
8
9
false
610
335
10
regular
100
25
1918
1010
8
81
false
1440
285
10
regular
200
190
1920
164
3
81
false
2015
283
10
regular
200
190
1921
40034
3
55
false
1901
244
10
regular
78
78
1922
964
3
9
false
1775
330
10
regular
100
25
8914
1420
2
49
false
1055
470
10
regular
78
78
8915
80
2
81
false
1310
487
10
regular
200
190
8916
40034
2
55
false
1331
238
10
regular
78
78
8917
1005
2
9
false
1172
330
10
regular
100
25
19
17
37
3
false
1645
460
12
regular
100
90
20
16
37
3
false
1905
461
12
regular
100
90
736
384
8
6
false
580
340
8
subunit
regular
160
80
738
2358
3
2
false
1750
345
8
subunit
regular
150
70
4866
757
2
2
false
1155
345
8
subunit
regular
150
70
687
324
44
8
729
736
290
1915
2773
Cofactor
689
326
44
3
731
738
292
1922
2782
Cofactor
4031
480
44
2
4839
4866
1716
8917
13899
Cofactor
2770
M845 380 C815 380 770 380 740 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2771
M445 380 C475 380 550 380 580 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2772
M510 480 C510 446 540 379 580 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2773
M150 100 L150 150 L200 100 z
10
true
18
2779
M1640 380 C1670 380 1720 380 1750 380
5
false
18
2780
M2015 378 C1985 378 1930 380 1900 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2781
M1940 322 C1939 349 1930 380 1900 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2782
M150 100 L150 150 L200 100 z
10
true
18
2783
M1695 460 C1695 430 1720 380 1750 380
5
false
18
2784
M1955 461 C1956 432 1930 380 1900 380
5
false
18
true
M 1912.9521331000901 497.75886816917995 L 1920 511 L 1927.943223090394 498.27580230677665
false
13894
M1045 380 C1086 379 1113 380 1155 380
5
false
18
13895
M1094 470 C1091 431 1125 380 1155 380
5
false
18
13896
M1410 487 C1409 434 1365 378 1305 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13897
M1440 380 C1395 381 1367 377 1305 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13898
M1370 316 C1368 361 1335 380 1305 380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
13899
M150 100 L150 150 L200 100 z
10
true
18
558
44
375
8
2062
1912
2770
Left
2063
1913
2771
Right
2064
1914
2772
Right
534
395
687
560
44
844
3
2069
1918
2779
Left
2070
1920
2780
Right
2071
1921
2781
Right
19
19
2783
Left
20
20
2784
Right
536
397
689
2710
44
288
2
8470
1912
13894
Left
8471
8914
13895
Left
8472
8915
13896
Right
8473
1918
13897
Right
8474
8916
13898
Right
2708
396
4031
93
13
1530
260
1.0
1.0
0
2
1
490
240
187164
1045
882
1.3
1.3
155
2
3
280
360
479844
805
560
1.6
1.6
0
3
14
327
267
126
M124 225 C124 175 174 125 224 125 C832 125 1621 125 2229 125 C2279 125 2329 175 2329 225 C2329 453 2329 749 2329 977 C2329 1027 2279 1077 2229 1077 C1621 1077 832 1077 224 1077 C174 1077 124 1027 124 977 C124 749 124 453 124 225
1
true
6
2205.0
952.0
451189
15
Intracellular Space
1035
140
20
1.9
1.9
160
15