574
Pathway
Histidine Biosynthesis
Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.
Metabolic
PW000810
Center
PathwayVisualizationContext1097
1756
2554
#000099
PathwayVisualization558
574
Histidine Biosynthesis
Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate.
This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine.
L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis.
Metabolic
3
109681
673
SubPathway
109181
190
Compound
2299
13192138
ADAMS E: The enzymatic synthesis of histidine from histidinol. J Biol Chem. 1954 Aug;209(2):829-46.
574
Pathway
2300
13271397
ADAMS E: L-Histidinal, a biosynthetic precursor of histidine. J Biol Chem. 1955 Nov;217(1):325-44.
574
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
23
Pseudomonas aeruginosa
287
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
19
Schizosaccharomyces pombe
4896
Eukaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
1
Cytosol
GO:0005829
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
11
Extracellular Space
GO:0005615
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
13
Endoplasmic Reticulum
GO:0005783
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
4
Peroxisome
GO:0005777
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
15
Nucleus
GO:0005634
27
Peroxisome Membrane
GO:0005778
6
Lysosome
GO:0005764
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
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
2
1
1
1
PW_BS000002
8
5
1
1
PW_BS000008
108
1
3
PW_BS000108
198
5
18
1
PW_BS000024
315
1
23
PW_BS000024
132
1
12
1
PW_BS000132
111
5
12
1
PW_BS000111
135
5
17
1
PW_BS000135
7
1
1
PW_BS000007
122
5
5
1
PW_BS000122
124
1
5
1
PW_BS000124
118
1
17
1
PW_BS000118
297
5
10
1
PW_BS000024
299
1
10
1
PW_BS000024
205
5
6
1
PW_BS000024
388
1
6
1
PW_BS000112
4
3
1
1
PW_BS000004
15
11
1
PW_BS000015
31
1
5
1
1
PW_BS000031
3
2
1
1
PW_BS000003
26
1
1
1
5
PW_BS000026
54
1
3
1
5
PW_BS000054
49
7
1
1
PW_BS000049
17
12
1
1
PW_BS000017
22
14
1
1
PW_BS000022
42
24
1
1
PW_BS000042
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
112
2
12
1
PW_BS000112
107
31
3
PW_BS000107
100
5
2
1
PW_BS000100
105
11
3
PW_BS000105
117
1
3
1
PW_BS000117
147
1
24
1
PW_BS000147
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
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
188
1
18
PW_BS000024
187
31
18
PW_BS000024
163
2
18
1
PW_BS000163
206
2
6
1
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
222
3
4
1
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
225
35
4
1
PW_BS000024
151
1
4
1
PW_BS000151
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
224
2
4
1
PW_BS000024
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
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
130
13
12
1
PW_BS000130
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
94
3
PW_BS000094
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
336
1
12
1
PW_BS000028
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
125
13
5
1
PW_BS000125
120
3
17
1
PW_BS000120
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
136
13
17
1
PW_BS000136
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
483
11
10
PW_BS000115
495
7
10
1
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
501
3
6
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
23
15
1
1
PW_BS000023
32
1
15
1
5
PW_BS000032
59
27
1
1
PW_BS000059
29
1
1
1
PW_BS000029
14
10
1
PW_BS000014
89
2
PW_BS000089
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
288
14
4
1
PW_BS000024
290
5
49
1
PW_BS000024
306
35
51
1
PW_BS000024
329
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
335
27
12
1
PW_BS000028
372
10
2
PW_BS000028
1
1
PW_BS000001
382
14
5
1
PW_BS000100
389
14
6
1
PW_BS000112
399
14
17
1
PW_BS000113
410
15
5
1
PW_BS000115
429
1
5
1
PW_BS000115
422
27
5
1
PW_BS000115
444
15
17
1
PW_BS000115
464
1
17
1
PW_BS000115
375
27
17
1
PW_BS000053
484
14
10
1
PW_BS000115
485
15
10
1
PW_BS000115
491
27
10
1
PW_BS000115
508
27
6
1
PW_BS000115
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
13
1
2
1
PW_BS000013
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
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
97
1
5
2
1
PW_BS000097
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
123
1
7
5
1
PW_BS000123
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
129
1
5
12
1
PW_BS000129
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
95
1
7
2
1
PW_BS000095
180
2
21
1
PW_BS000180
207
6
6
1
PW_BS000024
211
10
18
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
216
4
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
298
1
7
10
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
253
5
4
1
PW_BS000024
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
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
408
4
5
1
PW_BS000115
412
1
2
5
PW_BS000115
405
10
5
PW_BS000115
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
436
25
5
PW_BS000115
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
446
1
2
17
PW_BS000115
376
10
17
PW_BS000053
447
1
7
17
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
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
482
4
10
1
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
502
4
6
1
PW_BS000115
209
10
6
PW_BS000024
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
116
12
PW_BS000116
50
9
5
1
6
PW_BS000050
85
24
10
1
1
PW_BS000085
71
11
1
3
PW_BS000071
289
2
49
1
PW_BS000024
346
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5
12
6
PW_BS000028
423
9
5
5
6
PW_BS000115
458
9
5
17
6
PW_BS000115
47
19
1
4
PW_BS000047
241
5
29
PW_BS000024
257
15
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PW_BS000024
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190
Phosphoribosyl pyrophosphate
HMDB0000280
Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia).
7540-64-9
C00119
7339
17111
PRPP
7062
DB01632
O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
C5H13O14P3
InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1
PQGCEDQWHSBAJP-TXICZTDVSA-N
[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
390.0696
389.95181466
-1.53
7
phosphoribosylpyrophosphate
0
-4
FDB021928
5-phospho-a-d-ribose-1-diphosphate;5-phospho-a-d-ribosyl pyrophosphate;5-phospho-alpha-d-ribose 1-diphosphate;5-phospho-alpha-d-ribose-1-diphosphate;5-phospho-alpha-d-ribosyl pyrophosphate;5-phospho-alpha-d-riobse 1-diphosphate;5-phospho-alpha-delta-ribose 1-diphosphate;5-phospho-alpha-delta-ribose-1-diphosphate;5-phospho-alpha-delta-ribosyl pyrophosphate;5-phosphoribose 1-pyrophosphate;5-phosphoribosyl 1-diphosphate;5-phosphoribosyl a-1-pyrophosphate;5-phosphoribosyl-1-pyrophosphate;5-phosphorylribose 1-a-diphosphate;5-phosphorylribose 1-alpha-diphosphate;5-phosphorylribose 1-pyrophosphate;5-phosphorylribosyl 1-pyrophosphate;Pp-ribose-p;Prpp;Prib-pp;Phosphoribosyl pyrophosphate;Phosphoribosyl-1-pyrophosphate;Phosphoribosyl-pyrophosphate;Phosphoribosylpyrophosphorate;Phosphoribosylpyrophosphoric acid;A-d-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;A-d-5-phosphoribosyl 1-pyrophosphate;A-d-ribofuranose 5-phosphate 1-pyrophosphate;A-d-ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-d-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;Alpha-d-5-phosphoribosyl 1-pyrophosphate;Alpha-d-ribofuranose 5-phosphate 1-pyrophosphate;Alpha-d-ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-delta-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;Alpha-delta-5-phosphoribosyl 1-pyrophosphate;Alpha-delta-ribofuranose 5-phosphate 1-pyrophosphate;5-phosphoribosyl 1-pyrophosphate;5-phosphoribosyl diphosphate;Alpha-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-phosphoribosylpyrophosphoric acid;Phosphoribosylpyrophosphate;5-phospho-a-d-ribose 1-diphosphate;5-phospho-a-d-ribose 1-diphosphoric acid;5-phospho-alpha-d-ribose 1-diphosphoric acid;5-phospho-α-d-ribose 1-diphosphate;5-phospho-α-d-ribose 1-diphosphoric acid;Phosphoribosyl pyrophosphoric acid;5-phosphoribosyl 1-pyrophosphoric acid;5-phosphoribosyl diphosphoric acid;A-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);A-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);Alpha-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);α-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);α-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);A-phosphoribosylpyrophosphate;A-phosphoribosylpyrophosphoric acid;Alpha-phosphoribosylpyrophosphate;α-phosphoribosylpyrophosphate;α-phosphoribosylpyrophosphoric acid
PW_C000190
PRPP
1774
2
1815
8
5816
108
11780
198
42663
315
77176
132
78002
111
80680
135
111657
7
120160
122
121950
124
124503
118
125521
297
126346
299
127056
205
127709
388
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
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
1952
Phosphoribosyl-ATP
HMDB0003665
Phosphoribosyl-ATP belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Phosphoribosyl-ATP is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Outside of the human body, phosphoribosyl-ATP can be found in a number of food items such as chives, white lupine, redcurrant, and japanese persimmon. This makes phosphoribosyl-ATP a potential biomarker for the consumption of these food products. Phosphoribosyl-ATP takes part in the Histidine Metabolism pathway.[KEGG ID C02739]. Specifically, Phosphoribosyl-ATP is substrate for phosphoribosyl pyrophosphate synthetase 1.
C02739
1009
18263
984
NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O
C15H26N5O20P4
InChI=1S/C15H25N5O20P4/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(37-14)1-35-41(25,26)27)20(3-17-7)15-11(24)9(22)6(38-15)2-36-43(31,32)40-44(33,34)39-42(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H6,25,26,27,28,29,30,31,32,33,34)/p+1
KYTPWZMUSLPBJZ-UHFFFAOYSA-O
6-amino-9-[3,4-dihydroxy-5-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-9H-1λ⁵-purin-1-ylium
720.2835
720.012159345
-2.20
11
6-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-9-{3,4-dihydroxy-5-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl}-1λ⁵-purin-1-ylium
1
-4
FDB023212
1-(5-phospho-d-ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphate);1-(5-phospho-d-ribosyl)-atp;1-(5-phosphoribosyl)-atp;N1-(5-phospho-d-ribosyl)-atp
PW_C001952
P-ATP
5869
108
42690
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
7817
Phosphoribosyl-AMP
HMDB0012276
Phosphoribosyl-AMP is a nucleic acid component, a purine-related compound. It is an intermediate in histidine biosynthesis. It is converted from Phosphoribosyl-ATP via the enzyme phosphoribosyl-ATP diphosphatase (EC 3.6.1.31). It is then converted to phosphoribosylformiminoAICAR-phosphate via the enzyme phosphoribosyl-AMP cyclohydrolase (EC 3.5.4.19).
439795
PHOSPHORIBOSYL-AMP
30776608
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N
C15H23N5O14P2
InChI=1S/C15H23N5O14P2/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(33-14)1-31-35(25,26)27)20(3-17-7)15-11(24)9(22)6(34-15)2-32-36(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H2,25,26,27)(H2,28,29,30)/t5-,6-,8-,9-,10-,11-,14+,15-/m1/s1
RTQMRTSPTLIIHM-ZTRAZTMKSA-N
{[(2R,3S,4R,5R)-5-{1-[(2S,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
559.3157
559.071673493
-1.94
9
[(2R,3S,4R,5R)-5-{1-[(2S,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-iminopurin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
0
-4
1-(5-phosphoribosyl)-amp;5-phosphoribosyl-amp;N-(5'-phospho-d-ribosyl)-amp;N-(5-phospho-d-ribosyl)-amp;N1-(5-phospho-d-ribosyl)-amp
PW_C007817
P-AMP
40845
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide
Aicar, also known as Z-nucleotide or ZMP, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Aicar is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Aicar has been found in human skeletal muscle tissue, and has also been primarily detected in saliva. Within the cell, aicar is primarily located in the cytoplasm. Aicar exists in all living organisms, ranging from bacteria to humans. In humans, aicar is involved in the azathioprine action pathway, the mercaptopurine action pathway, the thioguanine action pathway, and the purine metabolism pathway. Aicar is also involved in several metabolic disorders, some of which include the lesch-nyhan syndrome (LNS) pathway, molybdenum cofactor deficiency, the gout or kelley-seegmiller syndrome pathway, and adenylosuccinate lyase deficiency. Outside of the human body, aicar can be found in herbs and spices. This makes aicar a potential biomarker for the consumption of this food product.
18406
NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C9H15N4O8P
InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
NOTGFIUVDGNKRI-UUOKFMHZSA-N
{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
338.2112
338.062749988
-2.08
6
aica ribonucleotide
0
-2
1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide;;5'-phosphoribosyl-5-amino-4-imidazolecarboxamide;5'-phospho-ribosyl-5-amino-4-imidazole carboxamide;Aicar;5-aminoimidazole-4-carboxamide ribotide;5-phosphoribosyl-4-carbamoyl-5-aminoimidazole;5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamide
PW_C040845
15'PAIC
7818
PhosphoribosylformiminoAICAR-phosphate
HMDB0012277
Phosphoribosylformiminoaicar-phosphate belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Phosphoribosylformiminoaicar-phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa).
C04896
1012
PHOSPHORIBOSYL-FORMIMINO-AICAR-P
987
NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O
C15H25N5O15P2
InChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)
QOUSHGMTBIIAHR-UHFFFAOYSA-N
({5-[(E)-N'-(4-carbamoyl-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acid
577.331
577.082238179
-2.00
10
{5-[(E)-N'-(5-carbamoyl-3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxyphosphonic acid
0
-4
C04896
Phosphoribosyl-formimino-aicar-p;Phosphoribosylformiminoaicar-p
PW_C007818
PRFAC-P
7819
Phosphoribulosylformimino-AICAR-P
HMDB0012278
Phosphoribulosylformimino-aicar-p, also known as prfar, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Phosphoribulosylformimino-aicar-p is slightly soluble (in water) and a moderately acidic compound (based on its pKa).
C04916
53481398
PHOSPHORIBULOSYL-FORMIMINO-AICAR-P
30776607
O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O
C15H25N5O15P2
InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/t7-,8+,10+,11+,12+,15+/m1/s1
BLKFNHOCHNCLII-IIZOACFYSA-N
{[(2R,3R)-5-[(E)-N'-{4-carbamoyl-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid
577.331
577.082238179
-2.04
10
[(2R,3R)-5-[(E)-N'-{5-carbamoyl-3-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxyphosphonic acid
0
-3
C04916
Phosphoribulosyl-formimino-aicar-p;Phosphoribulosylformiminoaicar-phosphate;Prfar
PW_C007819
PAICARP
500
L-Glutamine
HMDB0000641
Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such "cleansing" properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have "cleansing" properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. (http://en.wikipedia.org/wiki/glutamine).
56-85-9
C00064
5961
18050
GLN
5746
DB00130
N[C@@H](CCC(N)=O)C(O)=O
C5H10N2O3
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
ZDXPYRJPNDTMRX-VKHMYHEASA-N
(2S)-2-amino-4-carbamoylbutanoic acid
146.1445
146.069142196
-0.17
3
L-glutamine
0
0
FDB012164
(2s)-2,5-diamino-5-oxopentanoate;(2s)-2,5-diamino-5-oxopentanoic acid;(2s)-2-amino-4-carbamoylbutanoate;(2s)-2-amino-4-carbamoylbutanoic acid;(s)-2,5-diamino-5-oxopentanoate;(s)-2,5-diamino-5-oxopentanoic acid;2-aminoglutaramic acid;Cebrogen;Glavamin;Glumin;Glutamic acid 5-amide;Glutamic acid amide;Glutamine;L-(+)-glutamine;L-2-aminoglutaramic acid;L-2-aminoglutaramidic acid;L-glutamic acid 5-amide;L-glutamic acid gamma-amide;L-glutamid;L-glutamide;L-glutamin;L-glutamine;L-glutaminsaeure-5-amid;Levoglutamid;Levoglutamida;Levoglutamide;Levoglutamidum;Levoglutamina;Polyglutamine;Stimulina;Gamma-glutamine;Q;Glutamate 5-amide;Glutamate amide
PW_C000500
Gln
61
8
443
4
2701
2
3021
15
5658
107
5659
108
6068
157
6846
166
6847
3
8390
225
11793
198
12692
290
42352
318
42353
315
77016
253
77296
111
77333
133
78395
132
79164
114
79264
116
80652
135
113207
94
116207
109
120038
122
120348
406
121219
409
121961
124
122998
120
123789
137
124514
118
125416
297
125668
479
126359
299
126812
483
126956
205
127163
501
127718
388
128411
208
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
1801
5-Aminoimidazole-4-carboxamide
HMDB0003192
5-Aminoimidazole-4-carboxamide is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases. -- Pubchem.
360-97-4
C04051
9679
2030
CPD-3762
9298
NC(=O)C1=C(N)N=CN1
C4H6N4O
InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
DVNYTAVYBRSTGK-UHFFFAOYSA-N
4-amino-1H-imidazole-5-carboxamide
126.1166
126.054160834
-0.01
3
4-aminoimidazole-5-carboxamide
0
0
FDB023121
4-amino-5-imidazolecarboxamide;4-aminoimidazole-5-carboxamide;4-carbamoyl-5-aminoimidazole;4-carboxamido-5-aminoimidazole;5-amino-1h-imidazole-4-carboxamide;5-amino-4-imidazolecarboxamide;5-amino-imidazole-4-carboxamide;5-aminoimidazol-4-carboxamide;5-aminoimidazole-4-carboxamide ribotide;Aic;Aica;Aicar;Colahepat;4-amino-5-carbamoylimidazole;5(4)-amino-4(5)-imidazolecarboxamide;5-amino-4-imidazolecarboxyamide
PW_C001801
5Ai4Ca
1938
8
11839
198
78717
111
121917
122
124470
135
7755
D-Erythro-imidazole-glycerol-phosphate
HMDB0012208
D-Erythro-imidazole-glycerol-phosphate is an intermediate in Histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from Phosphoribulosyl-formimino-AICAR-phosphate then it is converted to Imidazole-acetol phosphate.
36244-87-8
C04666
440431
17805
D-ERYTHRO-IMIDAZOLE-GLYCEROL-P
389372
O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1
C6H11N2O6P
InChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3,5-6,9-10H,2H2,(H,7,8)(H2,11,12,13)/t5-,6+/m1/s1
HFYBTHCYPKEDQQ-RITPCOANSA-N
[(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid
238.1351
238.035472606
-1.03
5
(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxyphosphonic acid
0
-2
C04666
D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate;D-erythro-imidazole-glycerol 3-phosphate;D-erythro-imidazole-glycerol phosphate;D-erythro-imidazoleglycerol-phosphate;D-erythro-imidazole-glycerol 3-phosphoric acid;D-erythro-1-(imidazol-4-yl)glycerol 3-phosphoric acid;D-erythro-imidazole-glycerol phosphoric acid
PW_C007755
DEIGP
7782
Imidazole acetol-phosphate
HMDB0012236
Imidazole acetol-phosphate is involved in the histidine biosynthesis I pathway. Imidazole acetol-phosphate is created by the breakdown of D-erythro-imidazole-glycerol-phosphate into imidazole acetol-phosphate and H2O. Imidazoleglycerol-phosphate dehydratase catalyzes this reaction. Imidazole acetol-phosphate reacts with L-glutamate to produce L-histidinol-phosphate and 2-ketoglutarate. Histidinol-phosphate aminotransferase catalyzes this reaction.
99979-59-6
C01267
792
16426
IMIDAZOLE-ACETOL-P
770
OP(O)(=O)OCC(=O)CC1=CNC=N1
C6H9N2O5P
InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12)
YCFFMSOLUMRAMD-UHFFFAOYSA-N
[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid
220.1198
220.02490792
-1.17
3
3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid
0
-2
C01267
1-(1h-imidazol-4-yl)-3-(phosphonooxy)-2-propanone;3-(1h-imidazol-4-yl)-2-oxopropyl dihydrogen phosphate;3-(imidazol-4-yl)-2-oxopropyl dihydrogen phosphate;3-(imidazol-4-yl)-2-oxopropyl phosphate;Imidazole acetol phosphate;Imidazole acetol-p;Imidazole-acetol phosphate;3-(imidazol-4-yl)-2-oxopropyl phosphoric acid;3-(imidazol-4-yl)-2-oxopropyl dihydrogen phosphoric acid;Imidazole-acetol phosphoric acid
PW_C007782
Imidazo
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
40919
L-histidinol-phosphate
L-Histidinol-phosphate belongs to the class of organic compounds known as chlorinated biphenyls. These are organic compounds containing at least one chlorine atom attached to either benzene ring of the biphenyl moiety. L-Histidinol-phosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. L-Histidinol-phosphate may be a unique E.coli metabolite. L-Histidinol-phosphate participates in a number of enzymatic reactions. In particular, Oxoglutaric acid and L-histidinol-phosphate can be biosynthesized from imidazole acetol-phosphate and L-glutamic acid through the action of the enzyme histidinol-phosphate aminotransferase. In addition, L-Histidinol-phosphate can be converted into L-histidinol through the action of the enzyme imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase.
6242
OC1=CC(Cl)=CC=C1C1=CC=CC=C1
C12H9ClO
InChI=1S/C12H9ClO/c13-10-6-7-11(12(14)8-10)9-4-2-1-3-5-9/h1-8,14H
LMUKIFZFZRTUIY-UHFFFAOYSA-N
5-chloro-2-phenylphenol
204.65
204.0341926
-3.41
1
5-chloro-2-phenylphenol
0
0
PW_C040919
LHP
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
1889
L-Histidinol
HMDB0003431
L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumor cells of animal origin. (PMID 8297120). L-histidinol inhibits human Myristoyl- CoA:protein-myristoyltransferase (hNMT) (an essential eukaryotic enzyme that catalyzes the cotranslational transfer of myristate to the NH2-terminal glycine residue of a number of important proteins of diverse function). (PMID 9778369).
4836-52-6
C00860
165271
16255
L-HISTIDINOL-P
144886
N[C@H](CO)CC1=CN=CN1
C6H11N3O
InChI=1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)/t5-/m0/s1
ZQISRDCJNBUVMM-YFKPBYRVSA-N
(2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol
141.171
141.090211989
-0.04
3
HSO
0
2
FDB023173
(s)-beta-amino-1h-imidazole-4-propanol;Hso;Histidinol;Imidazole c-4(5) deriv. 4;4-[(s)-2-amino-3-hydroxypropyl]imidazole
PW_C001889
L-Hidol
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
7780
Histidinal
HMDB0012234
Histidinal is involved in the histidine biosynthesis I pathway. Histidinal is produced by the reaction between histidinol and NAD+, with NADH as a byproduct. The reaction is catalyzed by histidinol dehydrogenase. Histidinal reacts with NAD+ and H2O to produce L-histidine and NADH. Histidinol dehydrogenase catalyzes this reaction.
23784-15-8
775
HISTIDINAL
754
NC(CC1=CNC=N1)C=O
C6H9N3O
InChI=1S/C6H9N3O/c7-5(3-10)1-6-2-8-4-9-6/h2-5H,1,7H2,(H,8,9)
VYOIELONWKIZJS-UHFFFAOYSA-N
2-amino-3-(1H-imidazol-4-yl)propanal
139.1552
139.074561925
-0.27
2
2-amino-3-(1H-imidazol-4-yl)propanal
0
1
L-histidinal
PW_C007780
Histidi
116
L-Histidine
HMDB0000177
Histidine is an alpha-amino acid with an imidazole functional group. It is one of the 22 proteinogenic amino acids. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia. (PMID: 2084459). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-?B pathway, in adipocytes (PMID: 23361591). Low plasma concentrations of histidine are associated with protein-energy wasting, inflammation, oxidative stress, and greater mortality in chronic kidney disease patients (PMID: 18541578). Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all patients with low histamine levels. (http://www.dcnutrition.com ).
71-00-1
C00135
6274
15971
HIS
6038
DB00117
N[C@@H](CC1=CN=CN1)C(O)=O
C6H9N3O2
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
HNDVDQJCIGZPNO-YFKPBYRVSA-N
(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
155.1546
155.069476547
-0.40
3
L-histidine
0
0
FDB011856
(s)-1h-imidazole-4-alanine;(s)-2-amino-3-(4-imidazolyl)propionsaeure;(s)-4-(2-amino-2-carboxyethyl)imidazole;(s)-histidine;(s)-a-amino-1h-imidazole-4-propanoate;(s)-a-amino-1h-imidazole-4-propanoic acid;(s)-alpha-amino-1h-imidazole-4-propanoate;(s)-alpha-amino-1h-imidazole-4-propanoic acid;(s)-alpha-amino-1h-imidazole-4-propionate;(s)-alpha-amino-1h-imidazole-4-propionic acid;(s)1h-imidazole-4-alanine;3-(1h-imidazol-4-yl)-l-alanine;Amino-1h-imidazole-4-propanoate;Amino-1h-imidazole-4-propanoic acid;Amino-4-imidazoleproprionate;Amino-4-imidazoleproprionic acid;Glyoxaline-5-alanine;His;Histidine;L-(-)-histidine;H;L-histidin;(s)-α-amino-1h-imidazole-4-propanoate;(s)-α-amino-1h-imidazole-4-propanoic acid;(s)-a-amino-1h-imidazole-4-propionate;(s)-a-amino-1h-imidazole-4-propionic acid;(s)-α-amino-1h-imidazole-4-propionate;(s)-α-amino-1h-imidazole-4-propionic acid
PW_C000116
His
433
8
532
15
5024
50
5673
107
5674
108
42547
315
42563
318
77326
111
77583
114
78336
346
120339
122
120444
409
122990
135
123078
137
125661
297
125688
483
127155
205
127183
208
6665
ATP phosphoribosyltransferase
P60757
Involved in ATP phosphoribosyltransferase activity. Catalyzes the condensation of ATP and 5-phosphoribose 1- diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems to be controlled primarily by regulation of hisG enzymatic activity.
hisG
b2019
AP009048
3
2.4.2.17
8687
101
5911
Histidine biosynthesis bifunctional protein hisIE
P06989
Involved in phosphoribosyl-AMP cyclohydrolase activity. 1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5- phosphoribosyl)-AMP + diphosphate.
hisI
b2026
AP009048
3
3.5.4.19; 3.6.1.31
8688
101
6300
1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase
P10371
Involved in catalytic activity. 1-(5-phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5- ((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5- phosphoribosyl)imidazole-4-carboxamide.
hisA
b2024
AP009048
3
5.3.1.16
8689
101
7212
Imidazole glycerol phosphate synthase subunit hisH
P60595
Involved in transferase activity, transferring pentosyl groups. IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisH subunit provides the glutamine amidotransferase activity that produces the ammonia necessary to hisF for the synthesis of IGP and AICAR.
hisH
b2023
AP009048
3
2.4.2.-
8690
101
7337
Imidazole glycerol phosphate synthase subunit hisF
P60664
Involved in catalytic activity. IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisF subunit catalyzes the cyclization activity that produces IGP and AICAR from PRFAR using the ammonia provided by the hisH subunit.
hisF
b2025
AP009048
3
4.1.3.-
8691
101
5909
Histidine biosynthesis bifunctional protein hisB
P06987
Involved in catalytic activity. D-erythro-1-(imidazol-4-yl)glycerol 3- phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O.
hisB
b2022
AP009048
3
3.1.3.15; 4.2.1.19
8692
101
5908
Histidinol-phosphate aminotransferase
P06986
Involved in transferase activity. L-histidinol phosphate + 2-oxoglutarate = 3- (imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate.
hisC
b2021
AP009048
3
2.6.1.9
5910
Histidinol dehydrogenase
P06988
Involved in oxidoreductase activity. Catalyzes the sequential NAD-dependent oxidations of L- histidinol to L-histidinaldehyde and then to L-histidine.
hisD
b2020
AP009048
3
1.1.1.23
1484
ATP phosphoribosyltransferase
3
PW_P001484
1745
6665
2
1485
phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase
3
PW_P001485
1746
5911
1486
N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase
3
PW_P001486
1747
6300
1487
imidazole glycerol phosphate synthase
3
PW_P001487
1748
7212
1749
7337
1488
imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase
3
PW_P001488
1750
5909
2
1489
histidinol-phosphate aminotransferase
3
PW_P001489
1751
5908
2
1490
histidinal dehydrogenase / histidinol dehydrogenase
3
PW_P001490
1752
5910
2
2865
false
PW_R002865
Right
11367
190
1
Compound
false
11368
40034
1
Compound
false
11369
170
1
Compound
false
11370
1952
1
Compound
false
2826
1484
2.4.2.17
2866
false
PW_R002866
Right
11371
1952
1
Compound
false
11372
1420
1
Compound
false
11373
40034
1
Compound
false
11374
170
1
Compound
false
11375
7817
1
Compound
false
2827
1485
3.5.4.19
2867
false
PW_R002867
Right
11376
7817
1
Compound
false
11377
1420
1
Compound
false
11378
40845
1
Compound
false
2828
1485
2868
false
PW_R002868
Right
11379
40845
1
Compound
false
11380
7818
1
Compound
false
2829
1486
5.3.1.16
2869
false
PW_R002869
Right
11381
7819
1
Compound
false
11382
500
1
Compound
false
11383
95
1
Compound
false
11384
40034
1
Compound
false
11385
1801
1
Compound
false
11386
7755
1
Compound
false
2830
1487
2.4.2.-
2870
false
PW_R002870
Right
11387
7755
1
Compound
false
11388
1420
1
Compound
false
11389
7782
1
Compound
false
2831
1488
3.1.3.15
2871
false
PW_R002871
Right
11390
7782
1
Compound
false
11391
95
1
Compound
false
11392
134
1
Compound
false
11393
40919
1
Compound
false
2832
1489
2.6.1.9
2872
false
PW_R002872
Right
11394
40919
1
Compound
false
11395
1420
1
Compound
false
11396
1104
1
Compound
false
11397
1889
1
Compound
false
2833
1488
2873
false
PW_R002873
Right
11398
1889
1
Compound
false
11399
721
1
Compound
false
11400
1144
1
Compound
false
11401
40034
1
Compound
false
11402
7780
1
Compound
false
2834
1490
1.1.1.23
2874
false
PW_R002874
Right
11403
1420
1
Compound
false
11404
721
1
Compound
false
11405
7780
1
Compound
false
11406
40034
2
Compound
false
11407
1144
1
Compound
false
11408
116
1
Compound
false
2835
1490
2845
Inhibition
PW_I002845
5689
116
Compound
1
5690
1484
ProteinComplex
1
15447
190
3
false
324
401
10
regular
100
110
15448
40034
55
false
440
511
10
regular
78
78
15449
170
45
false
757
358
10
regular
63
43
15450
1952
3
false
829
396
10
regular
100
110
15451
1420
49
false
731
502
10
regular
78
78
15452
40034
55
false
924
677
10
regular
78
78
15453
170
45
false
767
684
10
regular
63
43
15454
7817
3
false
830
821
10
regular
100
110
15455
1420
49
false
941
928
10
regular
78
78
15456
40845
3
false
1295
809
10
regular
100
130
15457
7818
3
false
1295
389
10
regular
100
110
15458
7819
3
true
1294
391
10
regular
100
110
15459
500
3
false
1404
507
10
regular
100
100
15460
95
3
false
1734
506
10
regular
100
110
15461
40034
55
false
1915
521
10
regular
78
78
15462
1801
3
false
1949
289
10
regular
100
120
15463
7755
3
false
2149
379
10
regular
100
130
15464
1420
49
false
2005
685
10
regular
78
78
15465
7782
3
false
2148
769
10
regular
100
120
15466
95
3
false
1998
864
10
regular
100
110
15467
134
3
false
1988
1109
10
regular
100
110
15468
40919
3
false
2148
1274
10
regular
100
110
15469
1420
49
false
2009
1386
10
regular
78
78
15470
1104
46
false
1726
1209
10
regular
44
43
15471
1889
3
false
1578
1277
10
regular
100
100
15472
721
59
false
1528
1207
10
regular
50
30
15473
1144
60
false
1248
1208
10
regular
50
30
15474
40034
55
false
1199
1388
10
regular
78
78
15475
7780
3
false
1068
1276
10
regular
100
100
15476
1420
49
false
969
1373
10
regular
78
78
15477
721
59
false
988
1251
10
regular
50
30
15478
40034
55
false
669
1378
10
regular
78
78
15479
1144
60
false
703
1256
10
regular
50
30
15480
116
3
false
573
1276
10
regular
100
100
7777
6665
101
6
false
544
413
8
subunit
regular
160
80
7778
5911
101
2
false
804
586
8
subunit
regular
150
70
7779
5911
101
2
false
1065
839
8
subunit
regular
150
70
7780
6300
101
2
false
1270
654
8
subunit
regular
150
70
7781
7212
101
2
false
1479
370
8
subunit
regular
150
70
7782
7337
101
2
false
1554
410
8
subunit
regular
150
70
7783
5909
101
6
false
2119
586
8
subunit
regular
160
80
7784
5908
6
false
2118
1006
8
subunit
regular
160
80
7785
5909
101
6
false
1813
1287
8
subunit
regular
160
80
7786
5910
6
false
1333
1289
8
subunit
regular
160
80
7787
5910
6
false
788
1286
8
subunit
regular
160
80
6246
1484
558
7678
7777
6247
1485
558
7679
7778
6248
1485
558
7680
7779
6249
1486
558
7681
7780
6250
1487
558
7682
7781
7683
7782
6251
1488
558
7684
7783
6252
1489
558
7685
7784
6253
1488
558
7686
7785
6254
1490
558
7687
7786
6255
1490
558
7688
7787
23591
M423 454 C453 454 514 453 544 453
5
false
18
23592
M478 509 C471 445 514 453 544 453
5
false
18
23593
M789 401.5 C793 446.5 786 450 704 453
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23594
M829 451 C799 451 734 453 704 453
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23595
M879 506 C879 536 879 556 879 586
5
false
18
23596
M809 539 C867 537 879 556 879 586
5
false
18
23597
M927 716 C897 716 879 717 879 656
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23598
M826.5 704 C862.5 707 879 705 879 656
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23599
M880 821 C880 791 879 686 879 656
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23600
M930 876 C960 876 1035 874 1065 874
5
false
18
23601
M979 930 C978 876 999 875 1065 874
5
false
18
23602
M1295 874 C1265 874 1245 874 1215 874
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23603
M1345 809 C1345 779 1345 754 1345 724
5
false
18
23604
M1345 499 C1345 529 1345 624 1345 654
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23605
M1394 446 C1424 446 1524 445 1554 445
5
false
18
23606
M1453 508 C1451 433 1473 447 1554 445
5
false
18
23607
M1783 507 C1778 458 1781 446 1704 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23608
M1953 521 C1951 444 1953 445 1704 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23609
M2001 407 C2002 452 2001 447 1704 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23610
M2149 444 C2119 444 1734 445 1704 445
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23611
M2199 509 C2199 539 2199 556 2199 586
5
false
18
23612
M2086 722 C2163 724 2201 715 2199 666
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23613
M2198 769 C2198 739 2199 696 2199 666
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23614
M2198 889 C2198 919 2198 976 2198 1006
5
false
18
23615
M2100 920 C2174 919 2198 976 2198 1006
5
false
18
23616
M2086 1165 C2169 1162 2197 1153 2198 1086
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23617
M2198 1274 C2198 1244 2198 1116 2198 1086
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23618
M2148 1329 C2118 1329 2003 1327 1973 1327
5
false
18
23619
M2009 1425 C2014 1398 2003 1327 1973 1327
5
false
18
23620
M1770 1230.5 C1780 1270.5 1783 1327 1813 1327
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23621
M1678 1327 C1708 1327 1783 1327 1813 1327
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23622
M1578 1327 C1548 1327 1523 1329 1493 1329
5
false
18
23623
M1528 1222 C1525 1276 1523 1329 1493 1329
5
false
18
23624
M1298 1223 C1303 1275 1303 1329 1333 1329
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23625
M1277 1427 C1279 1382 1303 1329 1333 1329
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23626
M1168 1326 C1198 1326 1303 1329 1333 1329
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23627
M1008 1373 C1006 1332 971 1326 948 1326
5
false
18
23628
M1013 1281 C1013 1324 988 1325 948 1326
5
false
18
23629
M1066 1326 C1036 1326 978 1326 948 1326
5
false
18
23630
M708 1378 C705 1347 716 1327 788 1326
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23631
M728 1286 C721 1330 753 1324 788 1326
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23632
M673 1326 C703 1326 758 1326 788 1326
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3657122
M623 1276 C623 1246 625 852.5 625 822.5
148
false
18
3657123
M624 493 C624 523 625 795.5 625 825.5
148
false
18
false
true
M 99.56596732297899 282.6864219732177 L 91 295 L 82.43403267702101 307.3135780267823
3657124
M374 511 C374 537 375 622 374 660
5
false
18
4099
558
2865
14132
15447
23591
Left
14133
15448
23592
Left
14134
15449
23593
Right
14135
15450
23594
Right
4270
2826
6246
4100
558
2866
14136
15450
23595
Left
14137
15451
23596
Left
14138
15452
23597
Right
14139
15453
23598
Right
14140
15454
23599
Right
4271
2827
6247
4101
558
2867
14141
15454
23600
Left
14142
15455
23601
Left
14143
15456
23602
Right
4272
2828
6248
4102
558
2868
14144
15456
23603
Left
14145
15457
23604
Right
4273
2829
6249
4103
558
2869
14146
15458
23605
Left
14147
15459
23606
Left
14148
15460
23607
Right
14149
15461
23608
Right
14150
15462
23609
Right
14151
15463
23610
Right
4274
2830
6250
4104
558
2870
14152
15463
23611
Left
14153
15464
23612
Right
14154
15465
23613
Right
4275
2831
6251
4105
558
2871
14155
15465
23614
Left
14156
15466
23615
Left
14157
15467
23616
Right
14158
15468
23617
Right
4276
2832
6252
4106
558
2872
14159
15468
23618
Left
14160
15469
23619
Left
14161
15470
23620
Right
14162
15471
23621
Right
4277
2833
6253
4107
558
2873
14163
15471
23622
Left
14164
15472
23623
Left
14165
15473
23624
Right
14166
15474
23625
Right
14167
15475
23626
Right
4278
2834
6254
4108
558
2874
14168
15476
23627
Left
14169
15477
23628
Left
14170
15475
23629
Left
14171
15478
23630
Right
14172
15479
23631
Right
14173
15480
23632
Right
4279
2835
6255
7674
2845
558
1848
15480
3657122
Left
9063
6246
3657123
Right
109334
109681
558
14
false
299
660
16
regular
106039
15447
3657124
Right
186283
1460
635
1.0
1.0
0
2
92
479
481
1012
M124 225 C124 175 174 125 224 125 C861 125 1689 125 2326 125 C2376 125 2426 175 2426 225 C2426 620 2426 1132 2426 1527 C2426 1577 2376 1627 2326 1627 C1689 1627 861 1627 224 1627 C174 1627 124 1577 124 1527 C124 1132 124 620 124 225
1
true
6
2302.0
1502.0
1013
M225 325 C225 275 275 225 325 225 C901 225 1650 225 2226 225 C2276 225 2326 275 2326 325 C2326 658 2326 1092 2326 1425 C2326 1475 2276 1525 2226 1525 C1650 1525 901 1525 325 1525 C275 1525 225 1475 225 1425 C225 1092 225 658 225 325
1
true
6
2101.0
1300.0