597
Pathway
Glutathione Metabolism
The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene or Bromobenzene-2,3-oxide through a glutathione S-transferase
Metabolic
PW000833
Center
PathwayVisualizationContext1120
2800
2455
#000099
PathwayVisualization581
597
Glutathione Metabolism
The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene or Bromobenzene-2,3-oxide through a glutathione S-transferase
Metabolic
3
2256
238647
Apontoweil P, Berends W: Glutathione biosynthesis in Escherichia coli K 12. Properties of the enzymes and regulation. Biochim Biophys Acta. 1975 Jul 14;399(1):1-9.
597
Pathway
2257
17659286
Toledano MB, Kumar C, Le Moan N, Spector D, Tacnet F: The system biology of thiol redox system in Escherichia coli and yeast: differential functions in oxidative stress, iron metabolism and DNA synthesis. FEBS Lett. 2007 Jul 31;581(19):3598-607. doi: 10.1016/j.febslet.2007.07.002.
597
Pathway
1
Cell
CL:0000000
6
Myocyte
CL:0000187
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
3
Escherichia coli
562
Prokaryote
17
Rattus norvegicus
10116
Eukaryote
Rat
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
2
Bacteria
2
Prokaryote
Bacteria
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
19
Schizosaccharomyces pombe
4896
Eukaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
92
Bacillus subtilis
1423
Prokaryote
126
Lactobacillus delbrueckii subsp. bulgaricus LJJ
1585
Prokaryote
Lactobacillus
1
Cytosol
GO:0005829
2
Mitochondrion
GO:0005739
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
10
Cell Membrane
GO:0005886
6
Lysosome
GO:0005764
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
11
Extracellular Space
GO:0005615
35
Chloroplast
GO:0009507
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
13
Endoplasmic Reticulum
GO:0005783
4
Peroxisome
GO:0005777
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
15
Nucleus
GO:0005634
27
Peroxisome Membrane
GO:0005778
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
25
Golgi apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
40
Periplasm
GO:0042597
19
sarcoplasmic reticulum
GO:0016529
9
Muscle
BTO:0000887
141
18
1
Liver
BTO:0000759
72
9
24
Brain
BTO:0000142
89
16
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
28
Stomach
BTO:0001307
155
26
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
4
Adrenal Medulla
BTO:0000049
71
8
11
Heart
BTO:0000562
73
10
5
cardiocyte
BTO:0001539
2
1
1
1
PW_BS000002
3
2
1
1
PW_BS000003
8
5
1
1
PW_BS000008
1
1
PW_BS000001
4
3
1
1
PW_BS000004
14
10
1
PW_BS000014
9
6
1
1
PW_BS000009
42
24
1
1
PW_BS000042
50
9
5
1
6
PW_BS000050
26
1
1
1
5
PW_BS000026
54
1
3
1
5
PW_BS000054
111
5
12
1
PW_BS000111
113
6
12
1
PW_BS000113
117
1
3
1
PW_BS000117
118
1
17
1
PW_BS000118
132
1
12
1
PW_BS000132
107
31
3
PW_BS000107
108
1
3
PW_BS000108
105
11
3
PW_BS000105
147
1
24
1
PW_BS000147
157
2
24
1
PW_BS000157
94
3
PW_BS000094
85
24
10
1
1
PW_BS000085
187
31
18
PW_BS000024
188
1
18
PW_BS000024
72
5
1
3
PW_BS000072
71
11
1
3
PW_BS000071
205
5
6
1
PW_BS000024
207
6
6
1
PW_BS000024
224
2
4
1
PW_BS000024
151
1
4
1
PW_BS000151
225
35
4
1
PW_BS000024
220
1
4
PW_BS000024
198
5
18
1
PW_BS000024
161
3
18
1
PW_BS000161
222
3
4
1
PW_BS000024
31
1
5
1
1
PW_BS000031
289
2
49
1
PW_BS000024
290
5
49
1
PW_BS000024
315
1
23
PW_BS000024
318
31
23
PW_BS000024
320
11
23
PW_BS000024
253
5
4
1
PW_BS000024
133
3
12
1
PW_BS000133
112
2
12
1
PW_BS000112
346
9
5
12
6
PW_BS000028
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
135
5
17
1
PW_BS000135
124
1
5
1
PW_BS000124
122
5
5
1
PW_BS000122
407
2
5
1
PW_BS000115
406
3
5
1
PW_BS000115
126
6
5
1
PW_BS000126
418
24
5
1
PW_BS000115
423
9
5
5
6
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
119
2
17
1
PW_BS000119
120
3
17
1
PW_BS000120
443
6
17
1
PW_BS000115
454
24
17
1
PW_BS000115
458
9
5
17
6
PW_BS000115
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
299
1
10
1
PW_BS000024
297
5
10
1
PW_BS000024
481
2
10
1
PW_BS000115
479
3
10
1
PW_BS000115
301
6
10
1
PW_BS000024
489
24
10
1
PW_BS000115
388
1
6
1
PW_BS000112
206
2
6
1
PW_BS000024
501
3
6
1
PW_BS000115
506
24
6
1
PW_BS000115
15
11
1
PW_BS000015
60
25
1
PW_BS000060
61
25
1
7
PW_BS000061
74
1
3
PW_BS000074
51
8
1
PW_BS000051
353
25
12
7
PW_BS000028
326
8
12
PW_BS000028
352
25
12
PW_BS000028
436
25
5
PW_BS000115
437
25
5
7
PW_BS000115
416
8
5
PW_BS000115
472
25
17
7
PW_BS000115
452
8
17
PW_BS000115
471
25
17
PW_BS000115
49
7
1
1
PW_BS000049
17
12
1
1
PW_BS000017
22
14
1
1
PW_BS000022
10
1
7
1
1
PW_BS000010
18
13
1
1
PW_BS000018
70
28
5
1
1
PW_BS000070
103
3
3
1
PW_BS000103
100
5
2
1
PW_BS000100
155
3
24
1
PW_BS000155
159
24
PW_BS000159
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
152
8
4
PW_BS000152
101
5
3
1
PW_BS000101
163
2
18
1
PW_BS000163
219
31
4
PW_BS000024
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
160
1
18
1
PW_BS000160
170
18
PW_BS000170
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
195
13
18
PW_BS000024
249
13
4
1
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
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
293
4
1
PW_BS000024
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
114
11
12
PW_BS000114
130
13
12
1
PW_BS000130
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
383
7
5
1
PW_BS000100
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
336
1
12
1
PW_BS000028
109
32
3
PW_BS000109
409
11
5
PW_BS000115
384
12
5
1
PW_BS000100
125
13
5
1
PW_BS000125
137
11
17
PW_BS000137
121
12
17
1
PW_BS000121
136
13
17
1
PW_BS000136
483
11
10
PW_BS000115
495
7
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
208
11
6
PW_BS000024
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
16
2
1
2
PW_BS000016
13
1
2
1
PW_BS000013
32
1
15
1
5
PW_BS000032
5
4
1
1
PW_BS000005
39
7
1
1
3
PW_BS000039
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
27
15
1
PW_BS000027
46
1
1
4
PW_BS000046
29
1
1
1
PW_BS000029
66
18
5
1
8
PW_BS000066
23
15
1
1
PW_BS000023
91
8
5
1
1
PW_BS000091
89
2
PW_BS000089
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
104
14
3
1
PW_BS000104
129
1
5
12
1
PW_BS000129
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
199
14
18
1
PW_BS000024
211
10
18
PW_BS000024
216
4
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
190
11
18
PW_BS000024
277
1
2
18
PW_BS000024
329
14
12
1
PW_BS000028
333
1
2
12
PW_BS000028
332
1
7
12
1
PW_BS000028
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
335
27
12
1
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
184
1
2
1
PW_BS000024
382
14
5
1
PW_BS000100
412
1
2
5
PW_BS000115
429
1
5
1
PW_BS000115
123
1
7
5
1
PW_BS000123
433
1
14
5
1
PW_BS000115
408
4
5
1
PW_BS000115
410
15
5
1
PW_BS000115
405
10
5
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
399
14
17
1
PW_BS000113
446
1
2
17
PW_BS000115
464
1
17
1
PW_BS000115
447
1
7
17
1
PW_BS000115
468
1
14
17
1
PW_BS000115
374
4
17
1
PW_BS000053
444
15
17
1
PW_BS000115
376
10
17
PW_BS000053
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
484
14
10
1
PW_BS000115
485
15
10
1
PW_BS000115
478
10
10
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
389
14
6
1
PW_BS000112
516
15
6
1
PW_BS000115
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
28
1
16
1
1
PW_BS000028
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
110
2
3
1
PW_BS000110
127
1
16
5
1
PW_BS000127
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
95
1
7
2
1
PW_BS000095
180
2
21
1
PW_BS000180
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
356
25
12
1
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
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
482
4
10
1
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
502
4
6
1
PW_BS000115
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
47
19
1
4
PW_BS000047
313
23
PW_BS000024
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
35
5
19
1
4
PW_BS000035
649
32
92
PW_BS000508
311
32
2
PW_BS000024
628
32
126
PW_BS000503
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
458
Sodium
HMDB0000588
Sodium ions are necessary for regulation of blood and body fluids, transmission of nerve impulses, heart activity, and certain metabolic functions. Physiologically, it exists as an ion in the body. Sodium is needed by animals, which maintain high concentrations in their blood and extracellular fluids, but the ion is not needed by plants. The human requirement for sodium in the diet is less than 500 mg per day, which is typically less than a tenth as much as many diets "seasoned to taste." Most people consume far more sodium than is physiologically needed. For certain people with salt-sensitive blood pressure, this extra intake may cause a negative effect on health.
17341-25-2
C01330
923
29101
899
[Na+]
Na
InChI=1S/Na/q+1
FKNQFGJONOIPTF-UHFFFAOYSA-N
sodium(1+) ion
22.9898
22.989769675
0
sodium(1+) ion
1
1
FDB003523
Sodium;Sodium ion;Na(+);Na+
PW_C000458
Na+
2093
15
2094
2
2724
60
2725
61
3157
71
3158
72
3185
74
3615
51
4607
8
5860
105
5861
107
5862
108
7149
187
7150
188
42337
318
42338
315
78239
353
78243
326
78249
352
79047
132
122389
436
122390
437
122635
416
122636
124
124942
472
124946
452
124960
471
125209
118
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
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
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
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
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
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
826
γ-Glutamylcysteine
HMDB0001049
gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha Amino Acids and Derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG).
636-58-8
C00669
123938
17515
L-GAMMA-GLUTAMYLCYSTEINE
110467
DB03408
N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
C8H14N2O5S
InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
RITKHVBHSGLULN-WHFBIAKZSA-N
(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
250.272
250.062342258
-1.98
5
gamma-glutamylcysteine
0
-1
FDB003603
(des-gly)-Glutathione;3gc;5-L-Glutamyl-L-cysteine;5-L-Glutamylcysteine;H-Glu(Cys-OH)-OH;H-gamma-Glu-Cys-OH;L-g-Glutamyl-L-cysteine;L-gamma-Glutamyl-L-cysteine;L-gamma-Glutamylcysteine;N-(1-Carboxy-2-mercaptoethyl)-L-glutamine;N-L-gamma-Glutamyl-L-cysteine;Xn-L-g-glutamyl-glutamine;Xn-L-gamma-glutamyl-glutamine;g-Glutamylcysteine;g-L-Glutamyl-L-cysteine;gamma-Glu-Cys;gamma-Glutamylcysteine;gamma-L-Glutamyl-L-cysteine;Gammaglucys;Glu(-Cys);L-γ-Glutamyl-L-cysteine;G-Glu-Cys;γ-Glu-Cys;γ-Glutamylcysteine;γ-L-Glutamyl-L-cysteine;L-g-Glutamylcysteine;L-γ-Glutamylcysteine;γ-L-Glu-L-Cys;N-γ-Glutamylcysteine;N-L-γ-Glutamyl-cysteine;N-L-γ-Glutamyl-L-cysteine;gamma-L-Glu-L-Cys;N-L-gamma-Glutamyl-cysteine;N-γ-L-Glutamyl-L-cysteine
PW_C000826
γGluCys
175
8
4662
2
77780
111
80705
135
120096
122
125465
297
127002
205
78
Glycine
HMDB0000123
Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) Nonketotic hyperglycinaemia (OMIM 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). Mutations have been described in the GLDC (OMIM 238300), AMT (OMIM 238310), and GCSH (OMIM 238330) genes encoding the P-, T-, and H-proteins respectively. The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine and cerebrospinal fluid (CSF) with an increased CSF: plasma glycine ratio. (PMID 16151895).
56-40-6
C00037
5257127
15428
GLY
730
DB00145
NCC(O)=O
C2H5NO2
InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
DHMQDGOQFOQNFH-UHFFFAOYSA-N
2-aminoacetic acid
75.0666
75.032028409
0.87
2
glycine
0
0
FDB000484
2-aminoacetate;2-aminoacetic acid;Aciport;Amino-acetate;Amino-acetic acid;Aminoacetate;Aminoacetic acid;Aminoethanoate;Aminoethanoic acid;Glicoamin;Glycocoll;Glycolixir;Glycosthene;Gyn-hydralin;Padil;Aminoessigsaeure;G;Gly;Glycin;Glykokoll;Glyzin;H2n-ch2-cooh;Hgly;Leimzucker
PW_C000078
Gly
31
4
179
8
1812
2
1881
27
2829
29
5420
103
5454
120
5580
133
5640
107
5641
108
5863
105
6007
147
7014
160
7439
3
7441
166
7442
15
11794
198
11872
161
12429
151
15233
222
42419
318
42420
315
77644
336
77742
111
78022
132
78304
351
80708
135
120028
406
120097
122
120117
124
121687
429
122283
435
122850
118
124236
464
124837
470
125406
479
125466
297
125484
299
126448
499
126946
501
127003
205
127021
388
128018
517
1847
Oxidized glutathione
HMDB0003337
Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. 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.
27025-41-8
C00127
5255796
17858
OXIDIZED-GLUTATHIONE
950
NC(CCC(=O)NC(CSSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
C20H32N6O12S2
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)
YPZRWBKMTBYPTK-UHFFFAOYSA-N
2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
612.631
612.151961898
-3.18
10
oxiglutatione
0
-2
FDB023147
Gssg;Glutathione disulfide;L(-)-glutathione(oxidized);Oxiglutatione;(2s)-2-azaniumyl-4-{[(1r)-2-{[(2r)-2-[(4s)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoate
PW_C001847
GSSG
184
8
4878
3
77410
111
78012
112
80711
119
120103
122
120188
407
122840
135
125470
297
125545
481
127007
205
127078
206
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
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
2664
Naphthalene epoxide
HMDB0006215
Naphthalene epoxide is an epoxide derivative of naphthalene. The toxicity of naphthalene has to do with the Phase I metabolism of this compound by cytochrome P450 monooxygenases. Deactivation of naphthalene involves epoxidation followed by glutathione conjugation and mercapturic acid formation. Naphthalene is stereoselectively metabolized to form (1R,2S)-Naphthalene epoxide and (1S,2R)-Naphthalene epoxide in the presence of CYP1A1 and CYP1A2, CYP2E1,CYP3A4 and CYP2A6. (PMID: 16959878).
17180-88-0
108063
52431
97165
O1C2C=CC3=CC=CC=C3C12
C10H8O
InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H
XQIJIALOJPIKGX-UHFFFAOYSA-N
1aH,7bH-naphtho[1,2-b]oxirene
144.1699
144.057514878
-2.71
0
naphthalene 1,2-oxide
0
0
FDB023839
(1r,2s)-naphthalene 1,2-oxide;(1r,2s)-naphthalene epoxide;(1s,2r)-naphthalene epoxide;1,2-epoxy-1,2-dihydro-naphthalene;1,2-epoxy-1,2-dihydronaphthalene;Naphthalene 1,2-epoxide;Naphthalene-1,2-oxide
PW_C002664
Napepo
41144
(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene
HMDB0060299
(1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene is considered to be a practically insoluble (in water) and relatively neutral molecule.
11954046
[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C2=CC=CC=C2C=C[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=O
C20H25N3O7S
InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(25)23-14(19(28)22-9-17(26)27)10-31-18-12-4-2-1-3-11(12)5-7-15(18)24/h1-5,7,13-15,18,24H,6,8-10,21H2,(H,22,28)(H,23,25)(H,26,27)(H,29,30)/t13-,14-,15+,18+/m0/s1
UWBZAZWPTVBBEL-OIPACUDHSA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
451.493
451.141320859
-3.89
6
(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-2-hydroxy-1,2-dihydronaphthalen-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
0
-2
(1r, 2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-1,2-dihydro-1,2-dihyroxynaphthalene;(1r,2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-naphthalene-1,2-dihydrodiol;(2s)-2-amino-5-(2r)-1-(carboxymethylamino)-3-(1r,2r)-2-hydroxy-1,2-dihydronaphthalen-1-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid;3,4-dihydronaphthalene-3,4-diol;<i>cis</i>-1,2-dihydronaphthalene-1,2-diol;Cis-1,2-dihydroxy-1,2-dihydronaphthalene;L-gamma-glutamyl-s-(1r,2r)-2-hydroxy-1,2-dihydro-1-naphthalenyl-l-cysteinylglycine
PW_C041144
1R2ghd
41145
(1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene
HMDB0060300
(1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene is considered to be a practically insoluble (in water) and relatively neutral molecule.
11954044
[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@]1([H])C=CC2=CC=CC=C2[C@@]1([H])O)C(O)=NCC(O)=O)C(O)=O
C20H25N3O7S
InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(H,29,30)/t13-,14-,15+,18+/m0/s1
HBBDHJOSZGOTBV-OIPACUDHSA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1R,2R)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
451.493
451.141320859
-3.89
6
(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1R,2R)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
0
-2
(1r, 2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-1,2-dihydro-1,2-dihyroxynaphthalene;(1r,2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-naphthalene-1,2-dihydrodiol;(2s)-2-amino-5-(2r)-1-(carboxymethylamino)-3-(1r,2r)-1-hydroxy-1,2-dihydronaphthalen-2-ylsulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid;3,4-dihydronaphthalene-3,4-diol;<i>cis</i>-1,2-dihydronaphthalene-1,2-diol;Cis-1,2-dihydroxy-1,2-dihydronaphthalene;L-gamma-glutamyl-s-(1r,2r)-1-hydroxy-1,2-dihydro-2-naphthalenyl-l-cysteinylglycine
PW_C041145
1R2dhgd
41146
(1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene
HMDB0060302
(1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene is considered to be a practically insoluble (in water) and relatively neutral molecule.
11954044
[H][C@](N)(CCC(O)=N[C@@]([H])(CS[C@@]1([H])C=CC2=CC=CC=C2[C@]1([H])O)C(O)=NCC(O)=O)C(O)=O
C20H25N3O7S
InChI=1S/C20H25N3O7S/c21-13(20(29)30)6-8-16(24)23-14(19(28)22-9-17(25)26)10-31-15-7-5-11-3-1-2-4-12(11)18(15)27/h1-5,7,13-15,18,27H,6,8-10,21H2,(H,22,28)(H,23,24)(H,25,26)(H,29,30)/t13-,14-,15-,18-/m0/s1
HBBDHJOSZGOTBV-XSWJXKHESA-N
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
451.493
451.141320859
-3.89
6
(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
0
-2
(1r)-hydroxy-(2r)-glutathionyl-1,2-dihydronaphthalene;(1r, 2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-1,2-dihydro-1,2-dihyroxynaphthalene;(1r,2s)-1,2-dihydronaphthalene-1,2-diol;(1r,2s)-naphthalene-1,2-dihydrodiol;3,4-dihydronaphthalene-3,4-diol;<i>cis</i>-1,2-dihydronaphthalene-1,2-diol;Cis-1,2-dihydroxy-1,2-dihydronaphthalene
PW_C041146
1S2hgd
43027
Bromobenzene-2,3-oxide
HMDB0060446
Bromobenzene-2,3-oxide belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Bromobenzene-2,3-oxide is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
3036760
BrC1=CC=CC2OC12
C6H5BrO
InChI=1S/C6H5BrO/c7-4-2-1-3-5-6(4)8-5/h1-3,5-6H
RLBVUCNBWFGERE-UHFFFAOYSA-N
2-bromo-7-oxabicyclo[4.1.0]hepta-2,4-diene
173.007
171.952377429
-1.58
0
bromobenzene 2,3-oxide
0
0
(3<i>s</i>)-2,3-epoxysqualene;(s)-squalene-2,3-epoxide;2,3-edsq;2,3-epoxisqualene;2,3-oxidosqualene;2-bromo-7-oxabicyclo(4.1.0)hepta-2,4-diene;Bromobenzene 2,3-oxide;Bromobenzene-2,3-epoxide;Oxidosqualene;Squalene 2,3-epoxide;Squalene 2,3-oxide
PW_C043027
Brmbzox
41172
2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene
HMDB0060358
2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene is considered to be a practically insoluble (in water) and relatively neutral molecule.
11954067
[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C(Br)=CC=CC1([H])O)C(O)=NCC(O)=O)C(O)=O
C16H22BrN3O7S
InChI=1S/C16H22BrN3O7S/c17-8-2-1-3-11(21)14(8)28-7-10(15(25)19-6-13(23)24)20-12(22)5-4-9(18)16(26)27/h1-3,9-11,14,21H,4-7,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-,11?,14?/m0/s1
BYHFLDCNLZPMDY-PXAOEZFJSA-N
(2S)-2-amino-4-{[(1R)-2-[(2-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
480.331
479.03618341
-3.71
6
C16H22brN3O7S
0
-2
(2s)-2-amino-5-(2r)-3-(2-bromo-6-hydroxycyclohexa-2,4-dien-1-yl)sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid;L-gamma-glutamyl-s-(2-bromo-6-hydroxy-2,4-cyclohexadien-1-yl)-l-cysteinylglycine
PW_C041172
D2SGTBZ
106
an oxidized glutaredoxin
ProteinComplex
ProteinComplex
PW_EC000106
ox-GRX
105
a reduced glutaredoxin
Compound
PW_EC000105
red-GRX
7048
Sodium/glutamate symport carrier protein
P0AER8
Involved in glutamate:sodium symporter activity. Catalyzes the sodium-dependent uptake of extracellular glutamate.
gltS
b3653
AP009048
3
8571
109
136123
649
7203
Proton glutamate symport protein
P21345
Involved in sodium:dicarboxylate symporter activity. This carrier protein is part of the Na(+)-independent, binding-protein-independent glutamate-aspartate transport system.
gltP
b4077
AP009048
3
8570
109
135755
311
135770
628
7346
Glutamate/aspartate transport ATP-binding protein gltL
P0AAG3
Involved in nucleotide binding. Part of the binding-protein-dependent transport system for glutamate and aspartate. Probably responsible for energy coupling to the transport system.
gltL
b0652
AP009048
3
5633
109
135747
311
135762
628
136119
649
7047
Glutamate/aspartate transport system permease protein gltK
P0AER5
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane.
gltK
b0653
AP009048
3
5634
109
135748
311
135763
628
136120
649
7046
Glutamate/aspartate transport system permease protein gltJ
P0AER3
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane.
gltJ
b0654
AP009048
3
5635
109
135749
311
135764
628
136121
649
7489
Glutamate/aspartate periplasmic-binding protein
P37902
Part of the binding-protein-dependent transport system for glutamate and aspartate. Binds to both aspartate and glutamate.
gltI
b0655
AP009048
3
5636
109
135750
311
135765
628
136122
649
6019
Glutamate--cysteine ligase
P0A6W9
Involved in glutamate-cysteine ligase activity. ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine.
gshA
b2688
AP009048
3
6.3.2.2
6861
D-serine/D-alanine/glycine transporter
P0AAE1
Involved in transport. Permease that is involved in the transport across the cytoplasmic membrane of D-alanine, D-serine and glycine.
cycA
AE005174
3
8603
109
5870
Glutathione synthetase
P04425
Involved in ATP binding. ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione.
gshB
b2947
AP009048
3
6.3.2.3
5899
Glutathione reductase
P06715
Involved in oxidoreductase activity. Maintains high levels of reduced glutathione in the cytosol.
gor
b3500
AP009048
3
1.8.1.7
8740
101
6115
Glutathione S-transferase
P0A9D2
Involved in protein binding. Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
gst
b1635
AP009048
3
2.5.1.18
8741
101
1661
glutamate:sodium symporter
3
PW_P001661
1956
7048
1662
glutamate / aspartate : H+ symporter GltP
3
PW_P001662
1957
7203
1436
glutamate / aspartate ABC transporter
3
PW_P001436
1674
7346
1675
7047
1676
7046
1677
7489
1663
γ-glutamate-cysteine ligase
3
PW_P001663
1958
6019
1438
serine / alanine / glycine / cycloserine:H+symporter
3
PW_P001438
1679
6861
1664
glutathione synthetase
3
PW_P001664
1959
5870
4
1665
glutathione reductase
3
PW_P001665
1960
5899
2
3921
Glutathione S-transferase
3
PW_P003921
10894
6115
2
3052
false
PW_R003052
Right
12156
95
1
Compound
false
12157
414
1
Compound
false
12158
448
1
Compound
false
12159
1034
1
Compound
false
12160
1104
1
Compound
false
12161
40034
1
Compound
false
12162
826
1
Compound
false
3026
1663
6.3.2.2
3055
false
PW_R003055
Right
12174
1847
1
Compound
false
12175
40034
1
Compound
false
12176
146
1
Compound
false
12177
143
1
Compound
false
12178
80
2
Compound
false
3028
1665
1.8.1.7
5206
false
PW_R005206
Right
21091
2664
1
Compound
false
21092
80
1
Compound
false
21093
41144
1
Compound
false
5167
3921
2.5.1.18
5207
false
PW_R005207
Right
21094
2664
1
Compound
false
21095
80
1
Compound
false
21096
41145
1
Compound
false
5168
3921
5246
false
PW_R005246
Right
21277
80
1
Compound
false
21278
2664
1
Compound
false
21279
41146
1
Compound
false
5207
3921
5512
false
PW_R005512
Right
22426
80
1
Compound
false
22427
43027
1
Compound
false
22428
41172
1
Compound
false
5472
3921
3053
false
PW_R003053
Right
12163
826
1
Compound
false
12164
78
1
Compound
false
12165
414
1
Compound
false
12166
40034
1
Compound
false
12167
1104
1
Compound
false
12168
1034
1
Compound
false
12169
80
1
Compound
false
3027
1664
6.3.2.3
3054
true
PW_R003054
Right
12170
80
2
Compound
false
12171
106
1
ElementCollection
false
12172
1847
1
Compound
false
12173
105
1
ElementCollection
false
102
PW_RCT000102
Right
610
102
95
Compound
1
107
611
102
414
Compound
1
108
612
102
1420
Compound
1
108
613
102
1034
Compound
1
108
614
102
1104
Compound
1
108
615
102
40034
Compound
1
108
616
102
95
Compound
1
108
102
371
PW_T000371
Active
437
40034
1
Compound
107
108
Right
438
95
1
Compound
107
108
Right
317
1662
2015-04-01T21:34:26-06:00
2015-04-01T21:34:26-06:00
109
369
PW_T000369
Active
433
95
1
Compound
107
108
Right
434
458
1
Compound
107
108
Right
315
1661
2015-04-01T21:25:46-06:00
2015-04-01T21:25:46-06:00
109
352
PW_T000352
Active
403
78
1
Compound
107
108
Right
404
40034
1
Compound
107
108
Right
298
1438
2015-03-10T13:28:05-06:00
2015-03-10T13:28:05-06:00
109
16354
95
107
3
false
201
664
10
regular
100
110
16358
458
107
58
false
314
598
10
regular
78
78
16359
458
108
58
false
568
798
10
regular
78
78
16361
95
107
3
false
1412
217
10
regular
100
110
16364
40034
107
55
false
1509
338
10
regular
78
78
16365
40034
108
55
false
1519
543
10
regular
78
78
16367
95
107
3
false
2092
662
10
regular
100
110
16368
414
108
42
false
1846
617
10
regular
50
30
16369
1420
108
49
false
1826
528
10
regular
78
78
16370
1034
108
43
false
1877
817
10
regular
50
30
16371
1104
108
46
false
1882
880
10
regular
44
43
16372
40034
108
55
false
1856
953
10
regular
78
78
16373
95
108
3
false
1414
667
10
regular
100
110
16374
414
42
false
1349
807
10
regular
50
30
16375
448
3
false
1534
777
10
regular
100
100
16376
1034
43
false
1343
1002
10
regular
50
30
16377
1104
46
false
1348
1080
10
regular
44
43
16378
40034
55
false
1527
983
10
regular
78
78
16379
826
3
false
1415
1147
10
regular
100
110
16380
78
107
3
false
202
997
10
regular
100
100
16382
40034
107
55
false
312
1098
10
regular
78
78
16383
40034
108
55
false
577
1103
10
regular
78
78
16387
78
3
false
745
997
10
regular
100
100
16388
414
42
false
1145
917
10
regular
50
30
16389
40034
55
false
1224
1124
10
regular
78
78
16390
1104
46
false
1037
1214
10
regular
44
43
16391
1034
43
false
1046
1147
10
regular
50
30
16394
1847
3
false
591
1882
10
regular
100
110
16401
40034
55
false
668
2138
10
regular
78
78
16402
146
62
false
761
2127
10
regular
50
30
16403
143
61
false
1039
2112
10
regular
50
30
16404
80
3
false
1119
1732
10
regular
100
100
61825
2664
3
false
1224
1287
10
regular
100
110
61826
41144
3
false
1634
1269
10
regular
100
140
61827
2664
3
false
1279
1512
10
regular
100
110
61828
41145
3
false
1784
1494
10
regular
100
140
62046
2664
3
false
1309
1832
10
regular
100
110
62047
41146
3
false
1689
1709
10
regular
100
140
65504
43027
3
false
1359
2167
10
regular
100
110
65505
41172
3
false
1549
2009
10
regular
100
140
628
106
144
false
929
1667
12
regular
150
70
629
105
144
false
684
1667
12
regular
150
70
8113
7048
109
76
false
402
687
8
subunit
regular
150
70
8115
7203
109
76
false
1387
442
8
subunit
regular
150
70
8116
7346
109
76
false
1887
687
8
subunit
regular
150
70
8117
7047
109
76
false
1892
717
8
subunit
regular
150
70
8118
7046
109
76
false
1892
652
8
subunit
regular
150
70
8119
7489
109
76
false
1892
682
8
subunit
regular
150
70
8120
6019
2
false
1391
897
8
subunit
regular
150
70
8121
6861
109
76
false
396
1012
8
subunit
regular
150
70
8123
5870
8
false
1100
1009
8
subunit
regular
140
85
8125
5899
101
6
false
846
2039
8
subunit
regular
160
80
28770
6115
101
6
false
1419
1299
8
subunit
regular
160
80
28771
6115
101
6
false
1549
1524
8
subunit
regular
160
80
28838
6115
101
6
false
1459
1739
8
subunit
regular
160
80
30292
6115
101
6
false
1329
2039
8
subunit
regular
160
80
6529
1661
581
8020
8113
6531
1662
581
8022
8115
6532
1436
581
109
8023
8116
8024
8117
8025
8118
8026
8119
6533
1663
581
8027
8120
6534
1438
581
8028
8121
6536
1664
581
8030
8123
6538
1665
581
8032
8125
24187
3921
581
28458
28770
24188
3921
581
28459
28771
24248
3921
581
28526
28838
25523
3921
581
29977
30292
24808
M2092 717 C2007 716 2123 717 2042 717
5
false
18
24809
M1896 632 C1921 631 1966 649 1967 682
5
false
18
24810
M1904 567 C1967 564 1968 640 1967 682
5
false
18
24811
M1927 832 C1966 833 1968 835 1967 787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24812
M1926 901.5 C1967 901.5 1971 842 1967 787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24813
M1934 992 C1985 990 1972 919 1967 787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24814
M1514 722 C1735 723 1708 723 1887 722
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24815
M1464 777 C1464 807 1466 867 1466 897
5
false
18
24816
M1399 822 C1444 828 1468 844 1466 897
5
false
18
24817
M1534 827 C1462 828 1466 867 1466 897
5
false
18
24818
M1393 1017 C1452 1019 1465 1005 1466 967
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24819
M1392 1101.5 C1460 1097.5 1469 1030 1466 967
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24820
M1527 1022 C1499 1022 1466 997 1466 967
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24821
M1465 1147 C1465 1117 1466 997 1466 967
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24846
M641 1992 C641 2053 641 2011 642 2081 C725 2082 791 2081 846 2079
5
false
18
24847
M707 2138 C745 2082 783 2082 846 2079
5
false
18
24848
M786 2127 C793 2092 819 2079 846 2079
5
false
18
24849
M1064 2112 C1046 2080 1045 2082 1006 2079
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24850
M1169 1832 C1167 1924 1079 2081 1006 2079
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88696
M1324 1342 C1354 1342 1389 1341 1419 1339
5
false
18
88697
M1219 1782 C1252 1504 1349 1342 1419 1339
5
false
18
88698
M1634 1339 C1604 1339 1609 1339 1579 1339
5
false
18
true
M 25.946855044164835 1198.261556296296 L 11 1197 L 17.380887721185843 1210.5751343230784
false
88699
M1379 1567 C1424 1567 1501 1566 1549 1564
5
false
18
88700
M1219 1782 C1323 1640 1476 1568 1549 1564
5
false
18
88701
M1784 1564 C1754 1564 1739 1564 1709 1564
5
false
18
true
M 325.61352171083155 1064.9282229629628 L 310.6666666666667 1063.6666666666667 L 317.04755438785253 1077.2418009897451
false
88973
M1219 1782 C1249 1782 1429 1779 1459 1779
5
false
18
88974
M1359 1832 C1361 1787 1429 1779 1459 1779
5
false
18
88975
M1689 1779 C1659 1779 1649 1779 1619 1779
5
false
18
true
M 25.946855044164835 1115.3786590165769 L 11 1114.1171027202809 L 17.380887721185843 1127.6922370433592
false
93613
M1169 1832 C1169 1858 1196 2100 1329 2079
5
false
18
93614
M1409 2167 C1409 2138 1409 2164 1409 2119
5
false
18
93615
M1549 2079 C1519 2079 1519 2079 1489 2079
5
false
18
true
M 166.94685504416483 1335.5948896296293 L 152 1334.3333333333333 L 158.38088772118584 1347.9084676564116
false
3657874
M1509 377 C1453 379 1462 412 1462 442
83
false
18
3657875
M1519 582 C1485 582 1462 542 1462 512
83
false
18
true
M 756.9468550441649 410.261556296296 L 742 409 L 748.3808877211858 422.5751343230783
false
3657876
M1462 327 C1462 357 1462 412 1462 442
83
false
18
3657877
M1464 667 C1464 637 1462 542 1462 512
83
false
18
true
M 756.9468550441649 410.261556296296 L 742 409 L 748.3808877211858 422.5751343230783
false
3657882
M301 719 C311 720 392 722 402 722
83
false
18
3657883
M1414 722 C1326 721 645 722 552 722
83
false
18
true
M 471.94685504416486 174.26155629629605 L 457 173 L 463.38088772118584 186.57513432307834
false
3657884
M353 676 C351 707 367 721 402 722
83
false
18
3657885
M568 837 C539 840 477 806 477 757
83
false
18
true
M 471.94685504416486 174.26155629629605 L 457 173 L 463.38088772118584 186.57513432307834
false
3657886
M302 1047 C333 1046 357 1046 396 1047
83
false
18
3657887
M745 1047 C703 1049 586 1047 546 1047
83
false
18
true
M 282.94685504416486 914.261556296296 L 268 913 L 274.38088772118584 926.5751343230784
false
3657888
M351 1098 C344 1085 357 1047 396 1047
83
false
18
3657889
M616 1103 C616 1070 605 1047 546 1047
83
false
18
true
M 282.94685504416486 914.261556296296 L 268 913 L 274.38088772118584 926.5751343230784
false
3657890
M1415 1202 C1383 1203 1347 1202 1321 1202 C1320 1107 1320 1082 1320 1048 C1285 1049 1286 1048 1240 1049
5
false
18
3657891
M845 1047 C886 1048 1032 1047 1100 1049
5
false
18
3657892
M1170 947 C1170 977 1170 979 1170 1009
5
false
18
3657893
M1224 1163 C1174 1162 1170 1124 1170 1094
5
false
18
true
M 208.94685504416483 1295.261556296296 L 194 1294 L 200.38088772118584 1307.5751343230784
false
3657894
M1081 1235.5 C1155 1234.5 1170 1124 1170 1094
5
false
18
true
M 208.94685504416483 1295.261556296296 L 194 1294 L 200.38088772118584 1307.5751343230784
false
3657895
M1096 1162 C1161 1162 1167 1136 1170 1094
5
false
18
true
M 208.94685504416483 1295.261556296296 L 194 1294 L 200.38088772118584 1307.5751343230784
false
3657896
M1169 1732 C1169 1702 1170 1124 1170 1094
5
false
18
true
M 208.94685504416483 1295.261556296296 L 194 1294 L 200.38088772118584 1307.5751343230784
false
3657897
M1169 1832 C1167 1863 1156 1911.5 1142 1936.5
5
false
18
3657898
M641 1882 C641 1854 642 1820 642 1781 C729 1783 989 1778 1119 1782
5
false
18
true
M 158.94685504416483 1578.261556296296 L 144 1577 L 150.38088772118584 1590.5751343230784
false
3657899
M1004 1742 C1000 1772 963 1779.5 868 1780.5
5
false
18
3657900
M759 1737 C772 1781 811 1780.5 858 1780.5
5
false
18
true
M 158.94685504416483 1578.261556296296 L 144 1577 L 150.38088772118584 1590.5751343230784
false
4312
581
3052
15049
16373
24815
Left
15050
16374
24816
Left
15051
16375
24817
Left
15052
16376
24818
Right
15053
16377
24819
Right
15054
16378
24820
Right
15055
16379
24821
Right
4507
3026
6533
4316
581
3055
15072
16394
24846
Left
15073
16401
24847
Left
15074
16402
24848
Left
15075
16403
24849
Right
15076
16404
24850
Right
4510
3028
6538
18003
581
5206
69341
61825
88696
Left
69342
16404
88697
Left
69343
61826
88698
Right
18192
5167
24187
18004
581
5207
69344
61827
88699
Left
69345
16404
88700
Left
69346
61828
88701
Right
18193
5168
24188
18064
581
5246
69618
16404
88973
Left
69619
62046
88974
Left
69620
62047
88975
Right
18253
5207
24248
19096
581
5512
73891
16404
93613
Left
73892
65504
93614
Left
73893
65505
93615
Right
19279
5472
25523
797178
581
3053
117
3222143
16379
3657890
Left
3222144
16387
3657891
Left
3222145
16388
3657892
Left
3222146
16389
3657893
Right
3222147
16390
3657894
Right
3222148
16391
3657895
Right
3222149
16404
3657896
Right
752856
3027
6536
797179
581
3054
117
3222150
16404
3657897
Left
3222151
16394
3657898
Right
13670
628
3657899
Left
13671
629
3657900
Right
215
102
581
1297
16367
24808
Left
1298
16368
24809
Left
1299
16369
24810
Left
1300
16370
24811
Right
1301
16371
24812
Right
1302
16372
24813
Right
1303
16373
24814
Right
219
6532
136
78017
371
581
156739
16364
3657874
Left
156740
16365
3657875
Right
156741
16361
3657876
Left
156742
16373
3657877
Right
24658
6531
317
78019
369
581
156747
16354
3657882
Left
156748
16373
3657883
Right
156749
16358
3657884
Left
156750
16359
3657885
Right
24660
6529
315
78020
352
581
156751
16380
3657886
Left
156752
16387
3657887
Right
156753
16382
3657888
Left
156754
16383
3657889
Right
24661
6534
298
186305
597
1137
1.0
1.0
0
2
92
479
481
1061
M479 578 C479 528 529 478 579 478 C972 478 1482 478 1875 478 C1925 478 1975 528 1975 578 C1975 1077 1975 1725 1975 2224 C1975 2274 1925 2324 1875 2324 C1482 2324 972 2324 579 2324 C529 2324 479 2274 479 2224 C479 1725 479 1077 479 578
1
true
6
1496.0
1846.0
1062
M125 225 C125 175 175 125 225 125 C832 125 1620 125 2227 125 C2277 125 2327 175 2327 225 C2327 937 2327 1864 2327 2576 C2327 2626 2277 2676 2227 2676 C1620 2676 832 2676 225 2676 C175 2676 125 2626 125 2576 C125 1864 125 937 125 225
1
true
6
2202.0
2551.0