741
Pathway
Secondary Metabolites: Cysteine Biosynthesis from Serine
The pathway starts with a 3-phosphoglyceric acid interacting with an NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in an NADH, a hydrogen ion and a phosphohydroxypyruvic acid. This compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in a oxoglutaric acid and a DL-D-phosphoserine. The latter compound then interacts with a water molecule through a phosphoserine phosphatase resulting in a phosphate and an L-serine. The L-serine interacts with an acetyl-coa through a serine acetyltransferase resulting in a release of a Coenzyme A and a O-Acetylserine. The O-acetylserine then interacts with a hydrogen sulfide through a O-acetylserine sulfhydrylase A resulting in an acetic acid, a hydrogen ion and an L-cysteine
Metabolic
PW000977
Center
PathwayVisualizationContext1264
1305
2453
#000099
PathwayVisualization725
741
Secondary Metabolites: Cysteine Biosynthesis from Serine
The pathway starts with a 3-phosphoglyceric acid interacting with an NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in an NADH, a hydrogen ion and a phosphohydroxypyruvic acid. This compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in a oxoglutaric acid and a DL-D-phosphoserine. The latter compound then interacts with a water molecule through a phosphoserine phosphatase resulting in a phosphate and an L-serine. The L-serine interacts with an acetyl-coa through a serine acetyltransferase resulting in a release of a Coenzyme A and a O-Acetylserine. The O-acetylserine then interacts with a hydrogen sulfide through a O-acetylserine sulfhydrylase A resulting in an acetic acid, a hydrogen ion and an L-cysteine
Metabolic
3
109900
591
SubPathway
109431
644
Compound
2420
23417802
Smallbone K, Stanford NJ: Kinetic modeling of metabolic pathways: application to serine biosynthesis. Methods Mol Biol. 2013;985:113-21. doi: 10.1007/978-1-62703-299-5_7.
741
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
6
Myocyte
CL:0000187
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
7
Epithelial Cell
CL:0000066
10
Glial cell
CL:0000125
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
23
Pseudomonas aeruginosa
287
Prokaryote
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
21
Xenopus laevis
8355
Eukaryote
African clawed frog
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
5
Cytoplasm
GO:0005737
1
Cytosol
GO:0005829
35
Chloroplast
GO:0009507
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
25
Golgi apparatus
GO:0005794
4
Peroxisome
GO:0005777
12
Mitochondrial Inner Membrane
GO:0005743
6
Lysosome
GO:0005764
13
Endoplasmic Reticulum
GO:0005783
16
Lysosomal Lumen
GO:0043202
11
Extracellular Space
GO:0005615
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
10
Cell Membrane
GO:0005886
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
19
sarcoplasmic reticulum
GO:0016529
8
Smooth Endoplasmic Reticulum
GO:0005790
27
Peroxisome Membrane
GO:0005778
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
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
5
cardiocyte
BTO:0001539
8
5
1
1
PW_BS000008
2
1
1
1
PW_BS000002
117
1
3
1
PW_BS000117
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
160
1
18
1
PW_BS000160
225
35
4
1
PW_BS000024
322
1
23
1
PW_BS000024
132
1
12
1
PW_BS000132
111
5
12
1
PW_BS000111
124
1
5
1
PW_BS000124
122
5
5
1
PW_BS000122
118
1
17
1
PW_BS000118
135
5
17
1
PW_BS000135
299
1
10
1
PW_BS000024
388
1
6
1
PW_BS000112
4
3
1
1
PW_BS000004
3
2
1
1
PW_BS000003
10
1
7
1
1
PW_BS000010
43
25
1
1
PW_BS000043
5
4
1
1
PW_BS000005
54
1
3
1
5
PW_BS000054
49
7
1
1
PW_BS000049
17
12
1
1
PW_BS000017
29
1
1
1
PW_BS000029
9
6
1
1
PW_BS000009
18
13
1
1
PW_BS000018
28
1
16
1
1
PW_BS000028
6
1
3
1
PW_BS000006
31
1
5
1
1
PW_BS000031
95
1
7
2
1
PW_BS000095
103
3
3
1
PW_BS000103
112
2
12
1
PW_BS000112
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
100
5
2
1
PW_BS000100
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1
3
PW_BS000108
141
1
7
19
1
PW_BS000141
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3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
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PW_BS000001
178
3
21
1
PW_BS000178
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1
18
PW_BS000024
163
2
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1
PW_BS000163
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
198
5
18
1
PW_BS000024
222
3
4
1
PW_BS000024
226
4
4
1
PW_BS000024
224
2
4
1
PW_BS000024
216
4
18
1
PW_BS000024
249
13
4
1
PW_BS000024
298
1
7
10
1
PW_BS000024
300
13
10
1
PW_BS000024
223
12
4
1
PW_BS000024
315
1
23
PW_BS000024
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
336
1
12
1
PW_BS000028
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4
12
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1
7
12
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13
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PW_BS000130
113
6
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PW_BS000113
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1
3
12
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PW_BS000028
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25
12
1
PW_BS000028
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3
60
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PW_BS000028
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2
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PW_BS000119
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PW_BS000166
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PW_BS000094
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3
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PW_BS000115
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PW_BS000115
419
25
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PW_BS000115
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PW_BS000115
425
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PW_BS000115
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6
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PW_BS000126
429
1
5
1
PW_BS000115
383
7
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1
PW_BS000100
384
12
5
1
PW_BS000100
120
3
17
1
PW_BS000120
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
455
25
17
1
PW_BS000115
374
4
17
1
PW_BS000053
460
1
3
17
5
PW_BS000115
443
6
17
1
PW_BS000115
464
1
17
1
PW_BS000115
398
7
17
1
PW_BS000113
121
12
17
1
PW_BS000121
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
490
25
10
1
PW_BS000115
482
4
10
1
PW_BS000115
495
7
10
1
PW_BS000115
480
12
10
1
PW_BS000115
501
3
6
1
PW_BS000115
507
25
6
1
PW_BS000115
502
4
6
1
PW_BS000115
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
15
11
1
PW_BS000015
26
1
1
1
5
PW_BS000026
22
14
1
1
PW_BS000022
42
24
1
1
PW_BS000042
70
28
5
1
1
PW_BS000070
107
31
3
PW_BS000107
105
11
3
PW_BS000105
159
24
PW_BS000159
152
8
4
PW_BS000152
101
5
3
1
PW_BS000101
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
170
18
PW_BS000170
162
12
18
1
PW_BS000162
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
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
318
31
23
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
345
24
12
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
109
32
3
PW_BS000109
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
418
24
5
1
PW_BS000115
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
454
24
17
1
PW_BS000115
483
11
10
PW_BS000115
489
24
10
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
14
10
1
PW_BS000014
50
9
5
1
6
PW_BS000050
85
24
10
1
1
PW_BS000085
72
5
1
3
PW_BS000072
71
11
1
3
PW_BS000071
207
6
6
1
PW_BS000024
289
2
49
1
PW_BS000024
290
5
49
1
PW_BS000024
253
5
4
1
PW_BS000024
346
9
5
12
6
PW_BS000028
423
9
5
5
6
PW_BS000115
458
9
5
17
6
PW_BS000115
301
6
10
1
PW_BS000024
129
1
5
12
1
PW_BS000129
414
1
5
5
1
PW_BS000115
450
1
5
17
1
PW_BS000115
13
1
2
1
PW_BS000013
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
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
110
2
3
1
PW_BS000110
127
1
16
5
1
PW_BS000127
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
180
2
21
1
PW_BS000180
211
10
18
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
190
11
18
PW_BS000024
277
1
2
18
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
302
1
16
10
1
PW_BS000024
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
412
1
2
5
PW_BS000115
405
10
5
PW_BS000115
415
18
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
382
14
5
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PW_BS000100
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25
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PW_BS000115
446
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2
17
PW_BS000115
376
10
17
PW_BS000053
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1
16
17
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PW_BS000115
451
18
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
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PW_BS000113
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25
17
PW_BS000115
472
25
17
7
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
484
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10
1
PW_BS000115
209
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PW_BS000024
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18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
513
1
7
6
1
PW_BS000115
47
19
1
4
PW_BS000047
23
15
1
1
PW_BS000023
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
201
7
5
1
10
PW_BS000024
202
7
11
1
10
PW_BS000024
11
1
8
1
1
PW_BS000011
59
27
1
1
PW_BS000059
58
1
14
1
1
PW_BS000058
102
12
3
1
PW_BS000102
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
350
1
14
12
1
PW_BS000028
335
27
12
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PW_BS000028
288
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4
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PW_BS000024
433
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14
5
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PW_BS000115
422
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PW_BS000115
468
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14
17
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PW_BS000115
375
27
17
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PW_BS000053
491
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1
PW_BS000115
508
27
6
1
PW_BS000115
35
5
19
1
4
PW_BS000035
644
3-Phosphoglyceric acid
HMDB0000807
3-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia).
820-11-1
C00597
724
17050
G3P
704
OC(COP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
OSJPPGNTCRNQQC-UHFFFAOYSA-N
2-hydroxy-3-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.95
4
phosphoglycerate
0
-3
FDB022255
3-(dihydrogen phosphate)glycerate;3-(dihydrogen phosphate)glyceric acid;3-glycerophosphorate;3-glycerophosphoric acid;3-p-d-glycerate;3-p-glycerate;3-pga;3-pg;3-phospho-(r)-glycerate;3-phospho-d-glycerate;3-phospho-glycerate;3-phospho-glyceric acid;3-phosphoglycerate;3-phosphoglyceric acid;D-(-)-3-phosphoglyceric acid;D-glycerate 3-phosphate;G3p;Glycerate 3-phosphate;Glycerate-3-p;Glyceric acid 3-phosphate;Phosphoglycerate;Dl-glycerate 3-phosphate;Glycerate 3-phosphates;3-(dihydrogen phosphoric acid)glyceric acid;2-hydroxy-3-phosphonooxypropanoate;Dl-glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphates
PW_C000644
G3P
2051
8
2257
2
5743
117
5917
147
5948
151
6897
160
8358
225
42623
322
77111
132
78033
111
121192
124
121386
122
123763
118
123945
135
125960
299
127417
388
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-1
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
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
810
Phosphohydroxypyruvic acid
HMDB0001024
Phosphohydroxypyruvic acid, also known as 3-phosphonooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. Phosphohydroxypyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, phosphohydroxypyruvic acid is primarily located in the cytoplasm. Phosphohydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. Phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid; which is mediated by the enzyme D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase. Furthermore, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine; which is mediated by the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. Furthermore, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase. Furthermore, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine; which is catalyzed by the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. Furthermore, Phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through its interaction with the enzyme D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase. Finally, Phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine through its interaction with the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. In humans, phosphohydroxypyruvic acid is involved in the glycine and serine metabolism pathway. Phosphohydroxypyruvic acid is also involved in several metabolic disorders, some of which include the sarcosinemia pathway, the hyperglycinemia, non-ketotic pathway, dihydropyrimidine dehydrogenase deficiency (DHPD), and the NON ketotic hyperglycinemia pathway. Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG).
3913-50-6
C03232
105
30933
3-P-HYDROXYPYRUVATE
103
OC(=O)C(=O)COP(O)(O)=O
C3H5O7P
InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
LFLUCDOSQPJJBE-UHFFFAOYSA-N
2-oxo-3-(phosphonooxy)propanoic acid
184.0414
183.977289026
-1.14
3
phosphohydroxypyruvate
0
-3
FDB022377
2-oxo-3-(phosphonooxy)-propanoate;2-oxo-3-(phosphonooxy)-propanoic acid;3-phosphohydroxypyruvate;3-phosphohydroxypyruvic acid;3-phosphonooxypyruvate;3-phosphonooxypyruvic acid;Phosphohydroxypyruvate;Phosphohydroxypyruvic acid;Hydroxypyruvic acid phosphate;2-oxo-3-phosphonooxypropanoate;Hydroxypyruvate phosphate;Hydroxypyruvic acid phosphoric acid;3-phosphonatooxypyruvate
PW_C000810
3POHPyr
3479
2
78108
132
122157
124
124709
118
126315
299
127876
388
95
L-Glutamic acid
HMDB0000148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
(2S)-2-aminopentanedioic acid
147.1293
147.053157781
-0.26
3
L-glutamic acid
0
-1
FDB012535
(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeure
PW_C000095
Glu
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
7514
224
7518
151
8208
225
8373
220
11792
198
11855
161
12004
222
12621
31
12683
289
12697
290
42348
315
42349
318
42845
320
77020
253
77332
133
77525
112
77971
346
77977
327
77981
347
78291
345
80649
135
120023
124
120040
122
120086
407
120347
406
120692
126
120816
418
121147
423
121153
424
121157
425
122833
119
122997
120
123299
443
123401
454
123719
458
123725
459
123729
460
125401
299
125418
297
125457
481
125667
479
125769
301
125802
489
126941
388
126995
206
127162
501
127257
506
134
Oxoglutaric acid
HMDB0000208
Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).
328-50-7
C00026
51
30915
2-KETOGLUTARATE
50
DB02926
OC(=O)CCC(=O)C(O)=O
C5H6O5
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
KPGXRSRHYNQIFN-UHFFFAOYSA-N
2-oxopentanedioic acid
146.0981
146.021523302
-0.44
2
oxoglutarate
0
-2
FDB003361
2-ketoglutarate;2-ketoglutaric acid;2-oxo-1,5-pentanedioate;2-oxo-1,5-pentanedioic acid;2-oxoglutarate;2-oxoglutaric acid;2-oxopentanedioate;2-oxopentanedioic acid;Oxoglutarate;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acid
PW_C000134
AKG
15
2
42
3
141
4
146
8
499
18
673
31
1108
42
1263
5
1447
50
1455
26
1467
54
5375
103
5414
117
5438
118
5564
132
6008
147
6036
155
6069
157
6092
161
6482
178
6530
85
7471
222
7515
224
7519
151
8209
225
8374
220
11863
198
12681
289
77054
253
77135
133
77481
111
77523
112
77746
129
77967
345
77970
346
77976
327
77984
347
78425
334
80018
368
80694
135
113162
94
119972
406
120022
124
120084
407
120174
122
120552
414
120814
418
120989
408
121146
423
121152
424
121160
425
122757
120
122831
119
123186
450
123399
454
123554
374
123718
458
123724
459
123732
460
125357
479
125400
299
125455
481
125533
297
125800
489
125929
482
126900
501
126940
388
126993
206
127066
205
127255
506
127388
502
1214
DL-O-Phosphoserine
HMDB0001721
It is a normal metabolite found in human biofluids. (PMID 7693088, 7688003). The phosphoric ester of serine. -- Pubchem. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. - Wikipedia.
17885-08-4
C01005
106
37712
3-P-SERINE
104
NC(COP(O)(O)=O)C(O)=O
C3H8NO6P
InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
BZQFBWGGLXLEPQ-UHFFFAOYSA-N
2-amino-3-(phosphonooxy)propanoic acid
185.0725
185.008923505
-0.97
4
P-serine
0
-2
FDB022700
3-phospho-1-serine;3-phospho-serine;3-phosphoserine;Dl-o-phosphorylserine;Dl-o-phosphoserine;Dl-o-serine phosphate;Dl-serine dihydrogen phosphate;Dl-serine monophosphorate;Dl-serine monophosphoric acid;Energoserina;O-phospho-dl-serine;O-phospho-l-serine;O-phosphonoserine;P-serine;Phosphorylserine;Phosphoserine;Serine phosphate;Serine-3-phosphate;Serophen;2-amino-3-(phosphonooxy)propanoic acid;Dl-serine, dihydrogen phosphate (ester);2-amino-3-(phosphonooxy)propanoate;Dl-serine dihydrogen phosphoric acid;Dl-serine, dihydrogen phosphoric acid (ester)
PW_C001214
DL-OPPr
6516
108
6520
107
42588
318
42589
315
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
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
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
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
120
L-Serine
HMDB0000187
Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).
56-45-1
C00065
5951
17115
SER
5736
DB00133
N[C@@H](CO)C(O)=O
C3H7NO3
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
MTCFGRXMJLQNBG-REOHCLBHSA-N
(2S)-2-amino-3-hydroxypropanoic acid
105.0926
105.042593095
0.66
3
L-serine
0
0
FDB012739
(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionate
PW_C000120
Ser
344
8
1810
2
2617
4
5642
107
5643
108
5884
105
6011
147
6907
163
7086
201
7087
202
7090
71
7091
72
7202
160
7438
3
7443
15
7444
166
7522
224
8357
225
9154
249
12173
151
12625
18
15379
49
42335
318
42336
315
77320
111
78088
133
78112
132
79979
331
94858
383
115752
398
119924
122
122056
124
122136
406
122718
135
124667
118
124688
120
125314
297
126209
299
126293
479
126860
205
127771
388
127856
501
940
Acetyl-CoA
HMDB0001206
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
72-89-9
C00024
444493
15351
ACETYL-COA
392413
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C23H38N7O17P3S
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
ZSLZBFCDCINBPY-ZSJPKINUSA-N
{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
809.571
809.125773051
-2.27
9
acetyl-CoA
0
-4
FDB022491
Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme a
PW_C000940
Ac-CoA
213
4
385
8
842
3
2416
2
2446
5
2896
17
3340
11
4840
14
5278
103
5476
124
5733
108
6025
155
6077
161
6386
1
6470
178
6923
160
7106
163
7291
198
7460
222
8245
151
8277
210
12582
226
13012
299
42615
315
77121
133
77291
111
77562
112
77706
132
77994
115
78355
134
78433
334
80007
368
80634
119
80663
376
90124
170
119953
406
120145
405
120304
122
120632
407
122417
408
122626
384
122743
120
122959
135
123137
118
124986
374
125200
121
125343
479
125507
478
125633
297
126564
482
126572
481
126778
480
126886
501
127044
209
127394
205
127665
388
128137
502
128145
206
128374
391
1099
Coenzyme A
HMDB0001423
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).
85-61-0
C00010
6816
1146900
CO-A
6557
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
C21H36N7O16P3S
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
767.534
767.115208365
-2.22
10
coenzyme A
0
-4
FDB022614
Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
PW_C001099
CoA
211
4
386
8
845
3
879
22
892
17
2407
59
2414
2
2459
5
2813
29
2862
31
3342
11
3351
18
4618
10
4629
58
4842
14
4865
54
4879
6
5232
102
5247
104
5280
103
5477
124
5734
108
5777
101
6023
155
6075
161
6384
1
6468
178
6930
160
6961
162
6973
199
7083
188
7108
163
7293
198
7347
210
7458
222
8229
151
9081
226
9090
224
9124
170
9215
195
13013
299
15318
249
25488
49
42616
315
76907
293
77119
133
77222
134
77230
329
77292
111
77550
132
77555
334
77563
112
77633
336
77672
129
77996
115
78047
332
78056
350
78413
335
78567
130
79259
333
79974
331
80005
368
80620
118
80627
374
80635
119
80665
376
93828
382
93834
383
98674
288
110555
389
110561
390
115842
399
115847
398
119951
406
120147
405
120231
384
120305
122
120634
407
120762
117
121406
123
121421
433
121521
125
121666
429
121682
408
121714
414
122404
422
122741
120
122904
121
122960
135
123965
447
123979
468
124079
136
124220
464
124265
450
124974
375
125341
479
125509
478
125579
480
125592
484
125634
297
126084
481
126549
491
126560
482
126746
300
126884
501
127046
209
127109
391
127301
205
127540
206
127667
388
128121
508
128133
502
128340
395
1755
O-Acetylserine
HMDB0003011
O-Acetylserine (OASS) is an acylated amino acid derivative. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. Its presence in humans arises from either microbial metabolism in the gut or through consumption of foods containing OASS.
5147-00-2
C00979
6971051
17981
ACETYLSERINE
89874
CC(=O)OC[C@H](N)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
VZXPDPZARILFQX-BYPYZUCNSA-N
(2S)-3-(acetyloxy)-2-aminopropanoic acid
147.1293
147.053157781
0.07
2
O-acetyl-L-serine
0
0
FDB023094
O-acetyl-l-serine;O-acetyl-serine;O3-acetyl-l-serine;L-serine, acetate (ester);L-serine, acetic acid (ester)
PW_C001755
OAcSer
1827
Hydrogen sulfide
HMDB0003276
Hydrogen sulfide is a highly toxic and flammable gas. Because it is heavier than air it tends to accumulate at the bottom of poorly ventilated spaces. Although very pungent at first, it quickly deadens the sense of smell, so potential victims may be unaware of its presence until it is too late. H2S arises from virtually anywhere where elemental sulfur comes into contact with organic material, especially at high temperatures. Hydrogen sulfide is a covalent hydride chemically related to water (H2O) since oxygen and sulfur occur in the same periodic table group. It often results when bacteria break down organic matter in the absence of oxygen, such as in swamps, and sewers (alongside the process of anaerobic digestion). It also occurs in volcanic gases, natural gas and some well waters. It is also important to note that Hydrogen sulfide is a central participant in the sulfur cycle, the biogeochemical cycle of sulfur on Earth. As mentioned above, sulfur-reducing and sulfate-reducing bacteria derive energy from oxidizing hydrogen or organic molecules in the absence of oxygen by reducing sulfur or sulfate to hydrogen sulfide. Other bacteria liberate hydrogen sulfide from sulfur-containing amino acids. Several groups of bacteria can use hydrogen sulfide as fuel, oxidizing it to elemental sulfur or to sulfate by using oxygen or nitrate as oxidant. The purple sulfur bacteria and the green sulfur bacteria use hydrogen sulfide as electron donor in photosynthesis, thereby producing elemental sulfur. (In fact, this mode of photosynthesis is older than the mode of cyanobacteria, algae and plants which uses water as electron donor and liberates oxygen).
7783-06-4
C00283
18779926
16136
HS
391
S
H2S
InChI=1S/H2S/h1H2
RWSOTUBLDIXVET-UHFFFAOYSA-N
hydrogen sulfide
34.081
33.987720754
1
hydrogen sulfide
0
-1
FDB009599
Acide sulfhydrique;Dihydrogen disulfide;Dihydrogen monosulfide;Dihydrogen sulfide;Hepatate;Hepatic acid;Hepatic gas;Hydrogen monosulfide;Hydrogen sulfide;Hydrogen-sulfide;Hydrogene sulfure;Hydrosulfurate;Hydrosulfuric acid;Idrogeno solforato;Schwefelwasserstoff;Sewer gas;Siarkowodor;Sour gas;Stink damp;Sulfur hydride;Sulfur hydroxide;Sulfureted hydrogen;Sulfuretted hydrogen;Zwavelwaterstof;[sh2];H2s;Hydrogen sulphide;Sulfide;Sulfure d'hydrogene;Acide sulphhydrique;Dihydrogen monosulphide;Dihydrogen sulphide;Hydrogen monosulphide;Hydrogen-sulphide;Hydrogene sulphure;Hydrosulfate;Hydrosulphate;Hydrosulphuric acid;Sulphide;Sulphure d'hydrogene
PW_C001827
H2SO
714
8
77785
111
120572
122
123206
135
29
Acetic acid
HMDB0000042
Acetic acid is one of the simplest carboxylic acids. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A it is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted by certain bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and some other foods spoil. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent.
64-19-7
C00033
176
15366
ACET
171
DB03166
CC(O)=O
C2H4O2
InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
QTBSBXVTEAMEQO-UHFFFAOYSA-N
acetic acid
60.052
60.021129372
0.73
1
acetic acid
0
-1
DBMET00484
FDB008299
Acetate;Ethanoate;Ethanoic acid;Ethylate;Ethylic acid;Glacial acetate;Glacial acetic acid;Kyselina octova;Methanecarboxylate;Methanecarboxylic acid;Vinegar;Vinegar acid;Acide acetique;Acoh;Ch3-cooh;Ch3co2h;E 260;E-260;E260;Essigsaeure;Ethoic acid;Hoac;Ins no. 260;Meco2h;Mecooh;Ethoate
PW_C000029
Acoh
56
8
776
4
789
31
4283
2
4728
37
4730
36
6158
108
6223
166
6928
160
9267
26
12723
290
42702
315
49493
3
76998
294
77289
111
77823
129
77834
132
120059
122
120613
414
122456
124
122811
135
123238
450
125023
118
125437
297
126608
299
126975
205
128182
388
448
L-Cysteine
HMDB0000574
Cysteine is a naturally occurring, sulfur-containing amino acid that is found in most proteins, although only in small quantities. Cysteine is unique amongst the twenty natural amino acids as it contains a thiol group. Thiol groups can undergo oxidation/reduction (redox) reactions; when cysteine is oxidized it can form cystine, which is two cysteine residues joined by a disulfide bond. This reaction is reversible since the reduction of this disulphide bond regenerates two cysteine molecules. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Cysteine is often involved in electron-transfer reactions, and help the enzyme catalyze its reaction. Cysteine is also part of the antioxidant glutathione. N-Acetyl-L-cysteine (NAC) is a form of cysteine where an acetyl group is attached to cysteine's nitrogen atom and is sold as a dietary supplement. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder (cystine was first isolated from kidney stones). Oxidation of cysteine can produce a disulfide bond with another thiol and further oxidation can produce sulphfinic or sulfonic acids. The cysteine thiol group is also a nucleophile and can undergo addition and substitution reactions. Thiol groups become much more reactive when they are ionized, and cysteine residues in proteins have pKa values close to neutrality, so they are often in their reactive thiolate form in the cell. The thiol group also has a high affinity for heavy metals and proteins containing cysteine will bind metals such as mercury, lead, and cadmium tightly. Due to this ability to undergo redox reactions, cysteine has antioxidant properties. Cysteine is an important source of sulfur in human metabolism, and although it is classified as a non-essential amino acid, cysteine may be essential for infants, the elderly, and individuals with certain metabolic disease or who suffer from malabsorption syndromes. Cysteine may at some point be recognized as an essential or conditionally essential amino acid (Wikipedia). Cysteine is important in energy metabolism. As cystine, it is a structural component of many tissues and hormones. Cysteine has clinical uses ranging from baldness to psoriasis to preventing smoker's hack. In some cases, oral cysteine therapy has proved excellent for treatment of asthmatics, enabling them to stop theophylline and other medications. Cysteine also enhances the effect of topically applied silver, tin, and zinc salts in preventing dental cavities. In the future, cysteine may play a role in the treatment of cobalt toxicity, diabetes, psychosis, cancer, and seizures (http://www.dcnutrition.com/AminoAcids/).
52-90-4
C00097
5862
17561
CYS
5653
DB00151
N[C@@H](CS)C(O)=O
C3H7NO2S
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
XUJNEKJLAYXESH-REOHCLBHSA-N
(2R)-2-amino-3-sulfanylpropanoic acid
121.158
121.019749163
-0.72
3
L-cysteine
0
0
DBMET00503
FDB012678
(+)-2-amino-3-mercaptopropionic acid;(2r)-2-amino-3-mercaptopropanoate;(2r)-2-amino-3-mercaptopropanoic acid;(2r)-2-amino-3-sulfanylpropanoate;(2r)-2-amino-3-sulfanylpropanoic acid;(r)-(+)-cysteine;(r)-2-amino-3-mercaptopropanoate;(r)-2-amino-3-mercaptopropanoic acid;(r)-2-amino-3-mercapto-propanoate;(r)-2-amino-3-mercapto-propanoic acid;(r)-cysteine;2-amino-3-mercaptopropanoate;2-amino-3-mercaptopropanoic acid;2-amino-3-mercaptopropionate;2-amino-3-mercaptopropionic acid;3-mercapto-l-alanine;Acetylcysteine;B-mercaptoalanine;Carbocysteine;Cisteina;Cisteinum;Cystein;Cysteine;Cysteinum;Free cysteine;Half-cystine;L cysteine;L-(+)-cysteine;L-2-amino-3-mercaptopropanoate;L-2-amino-3-mercaptopropanoic acid;L-2-amino-3-mercaptopropionic acid;L-cystein;L-cysteine;Polycysteine;Thioserine;Alpha-amino-beta-thiolpropionic acid;Beta-mercaptoalanine;C;Cys;E920;L-zystein;(2r)-2-amino-3-sulphanylpropanoate;(2r)-2-amino-3-sulphanylpropanoic acid;L-2-amino-3-mercaptopropionate
PW_C000448
Cys
174
8
1867
2
2864
9
2870
15
5767
101
5801
108
6756
117
6759
107
7078
188
7496
224
7594
160
8256
227
8260
225
12012
281
12269
151
42651
315
43730
322
77778
111
77795
113
77796
132
80704
135
120125
122
120131
124
120580
126
122863
118
123210
443
125491
297
125498
299
127029
205
127035
388
43169
2-Aminomalonate semialdehyde
2-Aminomalonate semialdehyde, also known as L-alpha-formylglycine or 3-oxo-L-alanine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2-Aminomalonate semialdehyde is soluble (in water) and a moderately acidic compound (based on its pKa). 2-Aminomalonate semialdehyde may be a unique E.coli metabolite.
25244138
58671
[H][C@](N)(C=O)C([O-])=O
C3H4NO3
InChI=1S/C3H5NO3/c4-2(1-5)3(6)7/h1-2H,4H2,(H,6,7)/p-1/t2-/m0/s1
XMTCKNXTTXDPJX-REOHCLBHSA-M
(2S)-2-amino-3-oxopropanoate
102.07
102.019666573
0.75
1
L-3-oxoalaninate
-1
0
(2s)-2-amino-3-oxopropanoate;(2s)-2-amino-3-oxopropanoic acid;(s)-2-amino-3-oxopropanoate;(s)-2-amino-3-oxopropanoic acid;2-amino-3-oxo-propanoate;2-amino-3-oxo-propanoic acid;2-amino-3-oxopropionate;2-amino-3-oxopropionic acid;2-aminomalonate semialdehyde;2-aminomalonic acid semialdehyde;2-ammoniomalonate semialdehyde;2-ammoniomalonic acid semialdehyde;2-formylglycine;3-oxo-(9ci)-alanine;3-oxo-l-alanine;3-oxoalanine;A-formylglycine;Alpha-formylglycine;Amino-(8ci)malonaldehydate;Amino-(8ci)malonaldehydic acid;L-3-oxoalanine;L-alpha-formylglycine;L-amino-malonate semialdehyde;L-amino-malonic acid semialdehyde;L-aminomalonaldehydate;L-aminomalonaldehydic acid;L-serine semialdehyde [misnomer]
PW_C043169
2MnaSa
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
6142
D-3-phosphoglycerate dehydrogenase
P0A9T0
serA
b2913
AP009048
3
1.1.1.95
6419
Phosphoserine aminotransferase
P23721
Involved in metabolic process. Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine. Is involved in both pyridoxine and serine biosynthesis.
serC
b0907
AP009048
3
2.6.1.52
6194
94
8680
101
6286
Phosphoserine phosphatase
P0AGB0
Involved in catalytic activity. O-phospho-L(or D)-serine + H(2)O = L(or D)- serine + phosphate.
serB
b4388
AP009048
3
3.1.3.3
6116
Serine acetyltransferase
P0A9D4
Involved in transferase activity. Acetyl-CoA + L-serine = CoA + O-acetyl-L- serine.
cysE
b3607
AP009048
3
2.3.1.30
8681
101
6359
Cysteine synthase B
P16703
Involved in cysteine biosynthetic process from serine. Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product.
cysM
b2421
AP009048
3
2.5.1.47
6179
Cysteine synthase A
P0ABK5
Involved in cysteine biosynthetic process from serine. O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
cysK
b2414
AP009048
3
2.5.1.47; 4.5.1.5
7343
NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG
P39831
Involved in oxidoreductase activity. Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate.
ydfG
b1539
AP009048
3
1.1.1.-; 1.1.1.298
1464
D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase
3
PW_P001464
1723
6142
4
1465
3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase
3
PW_P001465
1724
6419
2
1466
phosphoserine phosphatase
3
PW_P001466
1725
6286
1467
serine acetyltransferase
3
PW_P001467
1726
6116
6
1468
cysteine synthase
3
PW_P001468
1727
6359
2
1469
O-acetylserine sulfhydrylase A
3
PW_P001469
1728
6179
2
3956
3-hydroxy acid dehydrogenase
3
PW_P003956
10936
7343
4
2843
false
PW_R002843
Right
11272
644
1
Compound
false
11273
721
1
Compound
false
11274
1144
1
Compound
false
11275
40034
1
Compound
false
11276
810
1
Compound
false
2804
1464
1.1.1.95
2844
false
PW_R002844
Right
11277
810
1
Compound
false
11278
95
1
Compound
false
11279
134
1
Compound
false
11280
1214
1
Compound
false
2805
1465
2.6.1.52
2845
false
PW_R002845
Right
11281
1214
1
Compound
false
11282
1420
1
Compound
false
11283
1104
1
Compound
false
11284
120
1
Compound
false
2806
1466
3.1.3.3
2846
false
PW_R002846
Right
11285
120
1
Compound
false
11286
940
1
Compound
false
11287
1099
1
Compound
false
11288
1755
1
Compound
false
2807
1467
2.3.1.30
2848
false
PW_R002848
Right
11293
1755
1
Compound
false
11294
1827
1
Compound
false
11295
40034
1
Compound
false
11296
29
1
Compound
false
11297
448
1
Compound
false
2809
1468
2.5.1.47
2810
1469
2.5.1.47
5862
false
PW_R005862
Both
23911
43169
1
Compound
false
23912
146
1
Compound
false
23913
40034
1
Compound
false
23914
143
1
Compound
false
23915
120
1
Compound
false
5828
3956
1.1.1.-
24223
644
3
false
1828
451
10
regular
100
120
24224
721
59
false
1748
431
10
regular
50
30
24225
1144
60
false
1459
566
10
regular
50
30
24226
40034
55
false
1459
387
10
regular
78
78
24227
810
3
false
1327
456
10
regular
100
110
24228
95
3
false
1197
561
10
regular
100
110
24229
134
3
false
927
361
10
regular
100
110
24230
1214
3
false
802
456
10
regular
100
110
24231
1420
49
false
899
577
10
regular
78
78
24232
1104
46
false
894
779
10
regular
44
43
24233
120
3
false
803
836
10
regular
100
100
24234
940
3
false
938
926
10
regular
100
100
24235
1099
85
false
1278
818
10
regular
50
30
24236
1755
3
false
1383
837
10
regular
100
100
24237
1827
3
false
1523
917
10
regular
100
110
24238
40034
55
false
1849
936
10
regular
78
78
24239
29
3
false
1863
746
10
regular
100
100
24240
448
3
false
2003
834
10
regular
100
100
69106
43169
3
false
303
831
10
regular
100
110
69107
146
62
false
453
811
10
regular
50
30
69108
40034
55
false
439
931
10
regular
78
78
69109
143
61
false
728
821
10
regular
50
30
11685
6142
8
false
1570
471
8
subunit
regular
140
85
11686
6419
101
6
false
1032
471
8
subunit
regular
160
80
11687
6286
2
false
777
668
8
subunit
regular
150
70
11688
6116
101
17
false
1068
848
8
subunit
regular
180
85
11689
6359
6
false
1603
800
19
subunit
regular
160
80
11690
6179
6
false
1648
845
19
subunit
regular
160
80
31816
7343
8
false
538
846
8
subunit
regular
140
85
9047
1464
725
11477
11685
9048
1465
725
11478
11686
9049
1466
725
11479
11687
9050
1467
725
11480
11688
9051
1468
725
11481
11689
9052
1469
725
11482
11690
26803
3956
725
31500
31816
36385
M1828 511 C1791 512 1738 511 1710 511
5
false
18
36386
M1773 461 C1773 507 1753 508 1710 511
5
false
18
36387
M1484 566 C1483 526 1505 515 1570 511
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36388
M1498 465 C1498 505 1520 513 1570 511
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36389
M1427 511 C1462 514 1534 509 1570 511
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36390
M1327 511 C1283 510 1233 510 1192 511
5
false
18
36391
M1247 561 C1248 517 1238 513 1192 511
5
false
18
36392
M977 471 C977 507 999 514 1032 511
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
true
M 1219.5 1837.9903810567666 L 1212 1825 L 1204.5 1837.9903810567666
false
36393
M902 511 C946 510 990 511 1032 511
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36394
M852 566 C852 596 852 638 852 668
5
false
18
36395
M899 616 C856 620 852 638 852 668
5
false
18
36396
M894 800.5 C852 798.5 852 768 852 738
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36397
M853 836 C853 806 852 768 852 738
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36398
M903 886 C933 886 1038 888 1068 888
5
false
18
36399
M988 926 C988 884 1038 888 1068 888
5
false
18
36400
M1303 848 C1304 875 1278 888 1248 888
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36401
M1383 887 C1353 887 1278 888 1248 888
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36402
M1483 887 C1513 887 1618 885 1648 885
5
false
18
36403
M1573 917 C1573 881 1618 885 1648 885
5
false
18
36404
M1888 936 C1887 900 1849 886 1808 885
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36405
M1913 846 C1912 882 1874 884 1808 885
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
36406
M2003 884 C1973 885 1892 884 1808 885
5
false
20
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
98365
M403 886 C433 886 508 886 538 886
5
false
18
true
M 25.946855044164835 1598.261556296296 L 11 1597 L 17.380887721185843 1610.5751343230784
false
98366
M478 841 C479 886 508 886 538 886
5
false
18
true
M 25.946855044164835 1598.261556296296 L 11 1597 L 17.380887721185843 1610.5751343230784
false
98367
M478 931 C478 891 508 886 538 886
5
false
18
true
M 25.946855044164835 1598.261556296296 L 11 1597 L 17.380887721185843 1610.5751343230784
false
98368
M753 851 C752 889 708 886 678 886
5
false
18
true
M 25.946855044164835 1598.261556296296 L 11 1597 L 17.380887721185843 1610.5751343230784
false
98369
M803 886 C773 886 708 886 678 886
5
false
18
true
M 25.946855044164835 1598.261556296296 L 11 1597 L 17.380887721185843 1610.5751343230784
false
3661169
M1928 511 C1970 512 1981 510 2008 511
5
false
18
6331
725
2843
22612
24223
36385
Left
22613
24224
36386
Left
22614
24225
36387
Right
22615
24226
36388
Right
22616
24227
36389
Right
6540
2804
9047
6332
725
2844
22617
24227
36390
Left
22618
24228
36391
Left
22619
24229
36392
Right
22620
24230
36393
Right
6541
2805
9048
6333
725
2845
22621
24230
36394
Left
22622
24231
36395
Left
22623
24232
36396
Right
22624
24233
36397
Right
6542
2806
9049
6334
725
2846
22625
24233
36398
Left
22626
24234
36399
Left
22627
24235
36400
Right
22628
24236
36401
Right
6543
2807
9050
6335
725
2848
22629
24236
36402
Left
22630
24237
36403
Left
22631
24238
36404
Right
22632
24239
36405
Right
22633
24240
36406
Right
6544
2809
9051
6545
2810
9052
20156
725
5862
78263
69106
98365
Left
78264
69107
98366
Left
78265
69108
98367
Left
78266
69109
98368
Right
78267
24233
98369
Right
20337
5828
26803
109572
109900
725
14
false
2008
476
16
regular
106264
24223
3661169
Right
186369
287
297
1.0
1.0
0
2
92
479
481
1363
M229 328 C229 278 279 228 329 228 C874 228 1582 228 2127 228 C2177 228 2227 278 2227 328 C2227 525 2227 782 2227 979 C2227 1029 2177 1079 2127 1079 C1582 1079 874 1079 329 1079 C279 1079 229 1029 229 979 C229 782 229 525 229 328
1
true
6
1998.0
851.0
1364
M125 225 C125 175 175 125 225 125 C832 125 1621 125 2228 125 C2278 125 2328 175 2328 225 C2328 484 2328 821 2328 1080 C2328 1130 2278 1180 2228 1180 C1621 1180 832 1180 225 1180 C175 1180 125 1130 125 1080 C125 821 125 484 125 225
1
true
6
2203.0
1055.0