549
Pathway
Glycolysis and Pyruvate Dehydrogenase
Fructose metabolism begins with the transport of beta-D-glucose 6-phosphate through a glucose PTS permease. This compound is isomerized by a glucose-6-phosphate isomerase resulting in fructose 6-phosphate. This compound can be phosphorylated by two different enzymes: a pyridoxal phosphatase/fructose 1,6-bisphosphatase or an ATP-driven 6-phosphofructokinase-1, resulting in fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in dihydroxyacetone phosphate or react with a phosphate through an NAD-dependent glyceraldehyde 3-phosphate dehydrogenase resulting in glyceric acid 1,3-biphosphate. This compound is dephosphorylated by a phosphoglycerate kinase resulting in 3-phosphoglyceric acid. This compound, in turn, can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through an AMP-driven phosphoenoylpyruvate synthase or an ADP-driven pyruvate kinase protein complex resulting in pyruvic acid. The pyruvic acid reacts with CoA through an NAD-driven pyruvate dehydrogenase complex resulting in carbon dioxide and an acetyl-CoA which gets incorporated into the TCA cycle pathway.
Metabolic
PW000785
Center
PathwayVisualizationContext1072
3404
3346
#000099
PathwayVisualization533
549
Glycolysis and Pyruvate Dehydrogenase
Fructose metabolism begins with the transport of beta-D-glucose 6-phosphate through a glucose PTS permease. This compound is isomerized by a glucose-6-phosphate isomerase resulting in fructose 6-phosphate. This compound can be phosphorylated by two different enzymes: a pyridoxal phosphatase/fructose 1,6-bisphosphatase or an ATP-driven 6-phosphofructokinase-1, resulting in fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in dihydroxyacetone phosphate or react with a phosphate through an NAD-dependent glyceraldehyde 3-phosphate dehydrogenase resulting in glyceric acid 1,3-biphosphate. This compound is dephosphorylated by a phosphoglycerate kinase resulting in 3-phosphoglyceric acid. This compound, in turn, can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through an AMP-driven phosphoenoylpyruvate synthase or an ADP-driven pyruvate kinase protein complex resulting in pyruvic acid. The pyruvic acid reacts with CoA through an NAD-driven pyruvate dehydrogenase complex resulting in carbon dioxide and an acetyl-CoA which gets incorporated into the TCA cycle pathway.
Metabolic
3
83303
595
SubPathway
81427
79
Compound
117
83449
590
SubPathway
81572
1134
Compound
117
83464
573
SubPathway
81587
644
Compound
117
83484
544
SubPathway
81607
940
Compound
117
2298
27766116
Hollinshead WD, Rodriguez S, Martin HG, Wang G, Baidoo EE, Sale KL, Keasling JD, Mukhopadhyay A, Tang YJ: Examining Escherichia coli glycolytic pathways, catabolite repression, and metabolite channeling using Deltapfk mutants. Biotechnol Biofuels. 2016 Oct 10;9:212. doi: 10.1186/s13068-016-0630-y. eCollection 2016.
549
Pathway
279538
Escherichia coli and Salmonella: Cellular and Molecular Biology (EcoSal). Online edition.
549
Pathway
1
Cell
CL:0000000
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
5
Hepatocyte
CL:0000182
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
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
19
Schizosaccharomyces pombe
4896
Eukaryote
21
Xenopus laevis
8355
Eukaryote
African clawed frog
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
110
Bacillus velezensis MRC5958
492670
Prokaryote
Velezensis
5
Cytoplasm
GO:0005737
2
Mitochondrion
GO:0005739
1
Cytosol
GO:0005829
35
Chloroplast
GO:0009507
3
Mitochondrial Matrix
GO:0005759
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
10
Cell Membrane
GO:0005886
7
Endoplasmic Reticulum Membrane
GO:0005789
19
sarcoplasmic reticulum
GO:0016529
15
Nucleus
GO:0005634
14
Mitochondrial Outer Membrane
GO:0005741
31
Periplasmic Space
GO:0005620
34
Plant-Type Vacuole
GO:0000325
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
6
Lysosome
GO:0005764
11
Extracellular Space
GO:0005615
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
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
40
Periplasm
GO:0042597
27
Peroxisome Membrane
GO:0005778
24
Mitochondrial Intermembrane Space
GO:0005758
8
Smooth Endoplasmic Reticulum
GO:0005790
1
Liver
BTO:0000759
72
9
25
Intestine
BTO:0000648
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
8
5
1
1
PW_BS000008
3
2
1
1
PW_BS000003
2
1
1
1
PW_BS000002
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
108
1
3
PW_BS000108
160
1
18
1
PW_BS000160
166
1
1
PW_BS000166
225
35
4
1
PW_BS000024
315
1
23
PW_BS000024
132
1
12
1
PW_BS000132
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
135
5
17
1
PW_BS000135
122
5
5
1
PW_BS000122
407
2
5
1
PW_BS000115
124
1
5
1
PW_BS000124
119
2
17
1
PW_BS000119
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
5
4
1
1
PW_BS000005
18
13
1
1
PW_BS000018
14
10
1
PW_BS000014
49
7
1
1
PW_BS000049
10
1
7
1
1
PW_BS000010
47
19
1
4
PW_BS000047
46
1
1
4
PW_BS000046
29
1
1
1
PW_BS000029
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
23
15
1
1
PW_BS000023
22
14
1
1
PW_BS000022
31
1
5
1
1
PW_BS000031
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
103
3
3
1
PW_BS000103
120
3
17
1
PW_BS000120
129
1
5
12
1
PW_BS000129
133
3
12
1
PW_BS000133
6
1
3
1
PW_BS000006
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
107
31
3
PW_BS000107
178
3
21
1
PW_BS000178
101
5
3
1
PW_BS000101
117
1
3
1
PW_BS000117
188
1
18
PW_BS000024
206
2
6
1
PW_BS000024
211
10
18
PW_BS000024
198
5
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
163
2
18
1
PW_BS000163
222
3
4
1
PW_BS000024
227
34
4
1
PW_BS000024
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
115
10
12
PW_BS000115
213
7
18
1
PW_BS000024
170
18
PW_BS000170
164
4
PW_BS000164
281
1
25
1
PW_BS000024
290
5
49
1
PW_BS000024
223
12
4
1
PW_BS000024
17
12
1
1
PW_BS000017
304
1
2
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
253
5
4
1
PW_BS000024
293
4
1
PW_BS000024
134
12
12
1
PW_BS000134
336
1
12
1
PW_BS000028
130
13
12
1
PW_BS000130
332
1
7
12
1
PW_BS000028
329
14
12
1
PW_BS000028
353
25
12
7
PW_BS000028
331
7
12
1
PW_BS000028
368
3
60
1
PW_BS000028
308
10
1
1
PW_BS000024
383
7
5
1
PW_BS000100
384
12
5
1
PW_BS000100
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
94
3
PW_BS000094
398
7
17
1
PW_BS000113
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
125
13
5
1
PW_BS000125
429
1
5
1
PW_BS000115
121
12
17
1
PW_BS000121
123
1
7
5
1
PW_BS000123
382
14
5
1
PW_BS000100
405
10
5
PW_BS000115
136
13
17
1
PW_BS000136
464
1
17
1
PW_BS000115
447
1
7
17
1
PW_BS000115
399
14
17
1
PW_BS000113
376
10
17
PW_BS000053
472
25
17
7
PW_BS000115
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
478
10
10
PW_BS000115
300
13
10
1
PW_BS000024
298
1
7
10
1
PW_BS000024
484
14
10
1
PW_BS000115
501
3
6
1
PW_BS000115
209
10
6
PW_BS000024
395
13
6
1
PW_BS000113
513
1
7
6
1
PW_BS000115
389
14
6
1
PW_BS000112
9
6
1
1
PW_BS000009
13
1
2
1
PW_BS000013
15
11
1
PW_BS000015
28
1
16
1
1
PW_BS000028
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
54
1
3
1
5
PW_BS000054
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
70
28
5
1
1
PW_BS000070
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
105
11
3
PW_BS000105
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
114
11
12
PW_BS000114
140
10
3
PW_BS000140
95
1
7
2
1
PW_BS000095
157
2
24
1
PW_BS000157
159
24
PW_BS000159
1
1
PW_BS000001
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
207
6
6
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
216
4
18
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
26
1
1
1
5
PW_BS000026
277
1
2
18
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
249
13
4
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
294
11
4
1
PW_BS000024
333
1
2
12
PW_BS000028
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
347
1
3
12
5
PW_BS000028
352
25
12
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
409
11
5
PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
425
1
3
5
5
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
137
11
17
PW_BS000137
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
482
4
10
1
PW_BS000115
483
11
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
495
7
10
1
PW_BS000115
480
12
10
1
PW_BS000115
502
4
6
1
PW_BS000115
208
11
6
PW_BS000024
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
16
2
1
2
PW_BS000016
32
1
15
1
5
PW_BS000032
39
7
1
1
3
PW_BS000039
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
66
18
5
1
8
PW_BS000066
51
8
1
PW_BS000051
91
8
5
1
1
PW_BS000091
89
2
PW_BS000089
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
335
27
12
1
PW_BS000028
184
1
2
1
PW_BS000024
433
1
14
5
1
PW_BS000115
410
15
5
1
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
468
1
14
17
1
PW_BS000115
444
15
17
1
PW_BS000115
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
485
15
10
1
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
516
15
6
1
PW_BS000115
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
313
23
PW_BS000024
42
24
1
1
PW_BS000042
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
195
13
18
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
327
1
1
12
5
PW_BS000028
345
24
12
1
PW_BS000028
310
31
2
PW_BS000024
424
1
1
5
5
PW_BS000115
418
24
5
1
PW_BS000115
459
1
1
17
5
PW_BS000115
454
24
17
1
PW_BS000115
489
24
10
1
PW_BS000115
506
24
6
1
PW_BS000115
141
1
7
19
1
PW_BS000141
50
9
5
1
6
PW_BS000050
156
12
24
1
PW_BS000156
177
1
21
1
PW_BS000177
85
24
10
1
1
PW_BS000085
346
9
5
12
6
PW_BS000028
367
1
60
1
PW_BS000028
423
9
5
5
6
PW_BS000115
458
9
5
17
6
PW_BS000115
11
1
8
1
1
PW_BS000011
102
12
3
1
PW_BS000102
288
14
4
1
PW_BS000024
707
1
25
PW_BS000512
280
31
25
PW_BS000024
609
5
110
1
PW_BS000503
610
1
110
PW_BS000503
613
32
110
PW_BS000503
79
Fructose 6-phosphate
HMDB0000124
Fructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia).
643-13-0
C00085
69507
15946
FRUCTOSE-6P
62713
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
C6H13O9P
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
GSXOAOHZAIYLCY-HSUXUTPPSA-N
{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
260.1358
260.029718526
-1.05
6
D-fructose 6-phosphate
0
-2
FDB021896
D-fructose 6-phosphate;D-fructose 6-phosphorate;D-fructose 6-phosphoric acid;D-fructose-6-p;D-fructose-6-phosphate;Fpc;Fru-6-p;Fructose 6-phosphate;Fructose-6-p;Fructose-6-phosphate;Fructose-6p;Neuberg ester
PW_C000079
Fru6P
388
8
1014
3
1785
2
5904
147
5932
151
6465
108
6878
160
12987
166
13297
225
42676
315
77093
132
77294
111
77919
112
80660
135
120142
122
120716
407
121178
124
123321
119
123750
118
125504
297
125944
299
127041
205
127404
388
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[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
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
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
833
Fructose 1,6-bisphosphate
HMDB0001058
Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.
488-69-7
C00354
445557
16905
FRUCTOSE-16-DIPHOSPHATE
393165
O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
C6H14O12P2
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
RNBGYGVWRKECFJ-ZXXMMSQZSA-N
{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
340.1157
339.996048936
-1.33
7
[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
0
-4
FDB022397
D-fructose 1,6-biphosphate;D-fructose 1,6-bis(dihydrogen phosphate);D-fructose 1,6-bisphosphate;D-fructose 1,6-diphosphate;D-fructose-1,6-bisphosphate;D-fructose-1,6-diphosphate;Diphosphofructose;Esafosfan;Esafosfina;Fdp;Fosfructose;Fructose 1,6-bis;Fructose 1,6-bisphosphate;Fructose 1,6-diphosphate;Harden-young ester;1,6-di-o-phosphono-alpha-d-fructofuranose;Alpha fructose 1,6-diphosphate;1,6-di-o-phosphono-a-d-fructofuranose;1,6-di-o-phosphono-α-d-fructofuranose
PW_C000833
Fru1,6P
1021
8
1790
2
5905
147
5933
151
6880
160
13358
225
77095
132
77931
111
120727
122
121180
124
123328
135
123752
118
125946
299
127406
388
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
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
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
983
Glyceric acid 1,3-biphosphate
HMDB0001270
1,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG have been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as Inherited Phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3 BPG). (PMID 3555887). 1,3-bisphosphoglycerate is the anion form of bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.(wikipedia).
1981-49-3
C00236
683
DPG
663
OC(COP(O)(O)=O)C(=O)OP(O)(O)=O
C3H8O10P2
InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
LJQLQCAXBUHEAZ-UHFFFAOYSA-N
{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
266.0371
265.9592695
-1.44
5
1,3-bisphospho-D-glycerate
0
-4
FDB022524
1,3-biphosphoglycerate;1,3-biphosphoglyceric acid;1,3-bis-phosphoglycerate;1,3-bisphosphoglycerate;1,3-diphosphateglycerate;1,3-diphosphoglycerate;13-dpg;2-hydroxy-3-(phosphonooxy)-propanoate;2-hydroxy-3-(phosphonooxy)-propanoic acid;2-hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphorate;2-hydroxy-3-(phosphonooxy)-propanoic acid 1-anhydride with phosphoric acid;3-p-glyceroyl-p;3-phospho-d-glyceroyl phosphate;3-phospho-d-glyceroyl-phosphate;3-phosphoglyceroyl phosphate;3-phosphoglyceroyl-p;3-phosphoglyceroyl-phosphate;Dpg;Glycerate 1,3-biphosphate;Glycerate 1,3-bisphosphate;Glycerate 1,3-diphosphate;Glyceric acid 1,3-biphosphate;P-glyceroyl-p;Phosphoglyceroyl-p
PW_C000983
GlyABp
1041
8
2253
2
5914
147
5944
151
6892
160
77106
132
78029
111
120754
122
121188
124
123351
135
123759
118
125785
297
125956
299
127240
205
127414
388
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
644
3-Phosphoglyceric acid
HMDB0000807
3-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia).
820-11-1
C00597
724
17050
G3P
704
OC(COP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
OSJPPGNTCRNQQC-UHFFFAOYSA-N
2-hydroxy-3-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.95
4
phosphoglycerate
0
-3
FDB022255
3-(dihydrogen phosphate)glycerate;3-(dihydrogen phosphate)glyceric acid;3-glycerophosphorate;3-glycerophosphoric acid;3-p-d-glycerate;3-p-glycerate;3-pga;3-pg;3-phospho-(r)-glycerate;3-phospho-d-glycerate;3-phospho-glycerate;3-phospho-glyceric acid;3-phosphoglycerate;3-phosphoglyceric acid;D-(-)-3-phosphoglyceric acid;D-glycerate 3-phosphate;G3p;Glycerate 3-phosphate;Glycerate-3-p;Glyceric acid 3-phosphate;Phosphoglycerate;Dl-glycerate 3-phosphate;Glycerate 3-phosphates;3-(dihydrogen phosphoric acid)glyceric acid;2-hydroxy-3-phosphonooxypropanoate;Dl-glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphates
PW_C000644
G3P
2051
8
2257
2
5743
117
5917
147
5948
151
6897
160
8358
225
42623
322
77111
132
78033
111
121192
124
121386
122
123763
118
123945
135
125960
299
127417
388
1870
2-Phospho-D-glyceric acid
HMDB0003391
2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase.
C00631
439278
17835
2-PG
388411
DB01709
OC[C@@H](OP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
GXIURPTVHJPJLF-UWTATZPHSA-N
(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.96
4
(+-)-2-phosphoglycerate
0
-3
FDB001407
(2r)-3-hydroxy-2-(phosphonooxy)propanoate;(2r)-3-hydroxy-2-(phosphonooxy)propanoic acid;2-phospho-d-glycerate;2-phospho-d-glyceric acid;3-d-hydroxy-2-phosphonooxy-propanoate;3-d-hydroxy-2-phosphonooxy-propanoic acid;D-glycerate 2-phosphate;2-phospho-(r)-glycerate;D-glyceric acid 2-phosphoric acid;2-phospho-(r)-glyceric acid
PW_C001870
2PDG
2263
2
5918
147
5949
151
6899
160
77113
132
121194
124
123765
118
125962
299
127418
388
180
Phosphoenolpyruvic acid
HMDB0000263
Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia).
138-08-9
C00074
1005
44897
PHOSPHO-ENOL-PYRUVATE
980
DB01819
OC(=O)C(=C)OP(O)(O)=O
C3H5O6P
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
DTBNBXWJWCWCIK-UHFFFAOYSA-N
2-(phosphonooxy)prop-2-enoic acid
168.042
167.982374404
-1.10
3
phosphoenolpyruvic acid
0
-3
FDB001451
2-hydroxy-acrylic acid dihydrogen phosphate;2-phosphonooxyprop-2-enoate;2-phosphonooxyprop-2-enoic acid;P-enol-pyruvate;Pep;Phosphoenolpyruvate
PW_C000180
Pep
419
8
2265
2
2396
4
5919
147
5950
151
6179
108
6901
160
11920
164
11931
225
42715
315
77114
132
77308
111
77963
133
120321
122
121196
124
121213
406
122976
135
123766
118
123783
120
125648
297
125963
299
127419
388
127516
205
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.02
5
adenylate
0
-2
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
164
Pyruvic acid
HMDB0000243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeure
PW_C000164
Pyr
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
7457
222
7495
220
8200
225
12622
31
15292
249
15349
18
77310
111
77972
346
77978
327
78090
112
80004
368
80042
367
80695
135
112879
94
115683
121
119950
406
120011
124
120175
122
120878
407
121148
423
121154
424
123454
119
123720
458
123726
459
125340
479
125390
299
125534
297
125854
481
126883
501
126931
388
127067
205
127858
206
1099
Coenzyme A
HMDB0001423
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).
85-61-0
C00010
6816
1146900
CO-A
6557
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
C21H36N7O16P3S
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
767.534
767.115208365
-2.22
10
coenzyme A
0
-4
FDB022614
Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
PW_C001099
CoA
211
4
386
8
845
3
879
22
892
17
2407
59
2414
2
2459
5
2813
29
2862
31
3342
11
3351
18
4618
10
4629
58
4842
14
4865
54
4879
6
5232
102
5247
104
5280
103
5477
124
5734
108
5777
101
6023
155
6075
161
6384
1
6468
178
6930
160
6961
162
6973
199
7083
188
7108
163
7293
198
7347
210
7458
222
8229
151
9081
226
9090
224
9124
170
9215
195
13013
299
15318
249
25488
49
42616
315
76907
293
77119
133
77222
134
77230
329
77292
111
77550
132
77555
334
77563
112
77633
336
77672
129
77996
115
78047
332
78056
350
78413
335
78567
130
79259
333
79974
331
80005
368
80620
118
80627
374
80635
119
80665
376
93828
382
93834
383
98674
288
110555
389
110561
390
115842
399
115847
398
119951
406
120147
405
120231
384
120305
122
120634
407
120762
117
121406
123
121421
433
121521
125
121666
429
121682
408
121714
414
122404
422
122741
120
122904
121
122960
135
123965
447
123979
468
124079
136
124220
464
124265
450
124974
375
125341
479
125509
478
125579
480
125592
484
125634
297
126084
481
126549
491
126560
482
126746
300
126884
501
127046
209
127109
391
127301
205
127540
206
127667
388
128121
508
128133
502
128340
395
940
Acetyl-CoA
HMDB0001206
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
72-89-9
C00024
444493
15351
ACETYL-COA
392413
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C23H38N7O17P3S
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
ZSLZBFCDCINBPY-ZSJPKINUSA-N
{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
809.571
809.125773051
-2.27
9
acetyl-CoA
0
-4
FDB022491
Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme a
PW_C000940
Ac-CoA
213
4
385
8
842
3
2416
2
2446
5
2896
17
3340
11
4840
14
5278
103
5476
124
5733
108
6025
155
6077
161
6386
1
6470
178
6923
160
7106
163
7291
198
7460
222
8245
151
8277
210
12582
226
13012
299
42615
315
77121
133
77291
111
77562
112
77706
132
77994
115
78355
134
78433
334
80007
368
80634
119
80663
376
90124
170
119953
406
120145
405
120304
122
120632
407
122417
408
122626
384
122743
120
122959
135
123137
118
124986
374
125200
121
125343
479
125507
478
125633
297
126564
482
126572
481
126778
480
126886
501
127044
209
127394
205
127665
388
128137
502
128145
206
128374
391
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
1906
β-D-Glucose 6-phosphate
HMDB0003498
Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high.
C01172
439427
17719
388538
O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1
NBSCHQHZLSJFNQ-VFUOTHLCSA-N
{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
β-D-glucose 6-phosphate
0
-2
FDB023183
Beta-d-glucose 6-(dihydrogen phosphate);Beta-d-glucose 6-phosphate;6-h2po3glcbeta;6-o-phosphono-beta-d-glucopyranose;Beta-d-glucose 6-phosphic acid;Beta-d-glucose-6-phosphate;B-d-glucose 6-phosphate;B-d-glucose 6-phosphoric acid;Beta-d-glucose 6-phosphoric acid;β-d-glucose 6-phosphate;β-d-glucose 6-phosphoric acid;6-o-phosphono-b-d-glucopyranose;6-o-phosphono-β-d-glucopyranose;B-d-glucose 6-(dihydrogen phosphate);B-d-glucose 6-(dihydrogen phosphoric acid);Beta-d-glucose 6-(dihydrogen phosphoric acid);β-d-glucose 6-(dihydrogen phosphate);β-d-glucose 6-(dihydrogen phosphoric acid);B-d-glucose-6-phosphate;B-d-glucose-6-phosphoric acid;Beta-d-glucose-6-phosphoric acid;β-d-glucose-6-phosphate;β-d-glucose-6-phosphoric acid
PW_C001906
BDGlu6P
1728
2
3649
29
5903
147
5931
151
6211
108
6288
107
6877
160
12982
166
13290
225
42381
318
42382
315
77092
132
79063
336
121177
124
122587
429
123749
118
125159
464
125943
299
127403
388
137064
707
137065
280
1134
Dihydroxyacetone phosphate
HMDB0001473
Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
57-04-5
C00111
668
16108
DIHYDROXY-ACETONE-PHOSPHATE
648
DB04326
OCC(=O)COP(O)(O)=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
GNGACRATGGDKBX-UHFFFAOYSA-N
(3-hydroxy-2-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.89
3
dihydroxyacetone-phosphate
0
-2
FDB001618
1,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acid
PW_C001134
Dhapp
1026
8
1474
2
3305
5
4253
42
5813
108
5908
147
5936
151
6884
160
42660
315
77098
132
77934
111
78374
345
78559
334
93824
124
110551
388
115839
118
120733
122
122564
418
122590
408
123333
135
125137
454
125162
374
125787
297
125950
299
126712
489
126736
482
127242
205
128303
506
128330
502
869
D-Glyceraldehyde 3-phosphate
HMDB0001112
Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.
591-59-3
C00661
729
17138
GAP
709
DB02263
OC(COP(O)(O)=O)C=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
LXJXRIRHZLFYRP-UHFFFAOYSA-N
(2-hydroxy-3-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.92
3
glyceraldehyde 3 phosphate
0
-2
FDB001619
2-hydroxy-3-(phosphonooxy)-propanal;3-phosphoglyceraldehyde;D-glyceraldehyde 3-phosphate;D-glyceraldehyde-3-p;Dl-glyceraldehyde 3-phosphate;Gap;Glyceraldehyde-3-p;Glyceraldehyde-3-phosphate;Glyceraldehyde-p;Glyceraldehyde-phosphate;2-hydroxy-3-(phosphonooxy)propanal;Gliceraldehido-3-fosfato;Glyceraldehyde 3-(dihydrogen phosphate);Glycerinaldehyd-3-phosphat;Glyzerinaldehyd-3-phosphat;(2-hydroxy-3-oxopropyl) dihydrogen phosphoric acid;Glyceraldehyde 3-(dihydrogen phosphoric acid);Glyceraldehyde-3-phosphoric acid
PW_C000869
Glyc3P
1027
8
1781
2
5907
147
5935
151
6883
160
12800
225
77014
253
77097
132
77935
111
120734
122
121183
124
123334
135
123754
118
125784
297
125949
299
127239
205
127409
388
1176
Mannitol 1-phosphate
HMDB0001530
Mannitol-1-phosphate is a sugar alcohol. Mannitol-1-phosphate dehydrogenase, (EC 1.1.1.17) reduces fructose 6-phosphate into mannitol 1-phosphate, in the mannitol cycle of organisms such as Lactobacillus plantarum, a lactic acid bacterium found in many fermented food products and in the gastrointestinal tract of mammals. Mannitol-1-phosphate is also produced in many organisms that have a range of biological interactions with humans: parasitic, mutualism, or commensalism (Examples. A. niger; A. parasiticus; B. subtilis; C. difficile; E. faecalis; E. coli; K. pneumoniae; L. salivarius; M. hyopneumoniae; M. mycoides; M. pneumoniae; P. multocida; S. typhi; S. typhimurium; S. aureus; S. pneumoniae; V. cholerae; V. parahaemolyticus; Y. pestis).
15806-48-1
C00644
130418
16298
MANNITOL-1P
115387
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
C6H15O9P
InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1
GACTWZZMVMUKNG-KVTDHHQDSA-N
{[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid
262.1517
262.04536859
-0.99
7
mannitol-1-phosphate
0
-2
FDB022673
D-mannitol-1-phosphate;Mannitol 1-phosphate;Mannitol-1-p;Mannitol-1-phosphate
PW_C001176
M1P
611
Mannitol
HMDB0000765
Mannitol is a diuretic and renal diagnostic aid related to sorbitol. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol is an alcohol and a sugar, or a polyol; it is similar to xylitol or sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a substance to adjust its pH, such as sodium bicarbonate. Mannitol is a non-permeating molecule i.e. it cannot cross biological membranes. Mannitol or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6) is an osmotic diuretic agent and a weak renal vasodilator. It is a sorbitol isomer.
69-65-8
C00392
6251
16899
6015
DB00742
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
C6H14O6
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
FBPFZTCFMRRESA-KVTDHHQDSA-N
(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
182.1718
182.07903818
0.10
6
mannitol
0
0
FDB001982
1,2,3,4,5,6-hexanehexol;Cordycepate;Cordycepic acid;D-mannitol;Diosmol;Hexahydroxyhexane;Hexanhexol;Invenex;Isotol;Manicol;Maniton s;Maniton-s;Manna sugar;Mannazucker;Mannidex;Mannigen;Mannistol;Mannit;Mannit p;Mannite;Mannitol;Mannogem 2080;Marine crystal;Mushroom sugar;Osmitrol;Osmofundin;Osmosal;Resectisol;Sdm no. 35;(2r,3r,4r,5r)-hexane-1,2,3,4,5,6-hexaol;(2r,3r,4r,5r)-hexane-1,2,3,4,5,6-hexol;D-(-)-mannitol;E 421;E-421;E421
PW_C000611
Manitol
6623
107
42383
318
137067
280
782
Dihydrolipoamide
HMDB0000985
Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG).
3884-47-7
C00579
663
17694
DIHYDROLIPOAMIDE
643
OC(=N)CCCCC(S)CCS
C8H17NOS2
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
VLYUGYAKYZETRF-UHFFFAOYSA-N
6,8-disulfanyloctanimidic acid
207.357
207.075155551
-3.32
4
dihydrothioctamide
0
0
FDB022352
6,8-bis-sulfanyloctanamide;6,8-dimercapto-octanamide;6,8-dimercaptooctanamide;6,8-disulfanyloctanamide;Dihydrolipoamide;Dihydrothioctamide;6,8-bis(sulphanyl)octanamide
PW_C000782
DHLipoa
212
4
1078
3
78774
112
79170
133
121451
407
121532
406
124009
119
124090
120
126077
481
127533
206
1174
S-Acetyldihydrolipoamide
HMDB0001526
S-Acetyldihydrolipoamide is a thio-acetylated form of dihydrolipoamide. The molecule is commonly conjugated to lysine residues. The structure shown is the free form of the molecule. Pyruvate dehydrogenase complex. The reaction is 2-(alpha-hydroxyethyl)-TPP + lipoamide => S-acetyldihydrolipoamide + TPP [Homo sapiens], occuring in mitochondrial matrix. (reactome.org). S-Acetyldihydrolipoamide is an intermediate in alanine, aspartate and pyruvate metabolism and glycolysis/gluconeogenesis (KEGG:C01136). It is converted from 2-hydroxyethyl-THPP and lipoamide via the enzyme pyruvate dehydrogenase (EC:1.2.4.1). It is then converted to acetyl-CoA via the enzyme pyruvate dehydrogenase E2 component (dihydrolipoamide acetyltransferase) (EC:2.3.1.12).
C01136
1076
16807
S-ACETYLDIHYDROLIPOAMIDE
1046
CC(=O)SC(CCS)CCCCC(N)=O
C10H19NO2S2
InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)
ARGXEXVCHMNAQU-UHFFFAOYSA-N
6-(acetylsulfanyl)-8-sulfanyloctanamide
249.393
249.085720237
-3.85
2
S(6)-acetyldihydrolipoamide
0
0
FDB022671
6-acetylsulfanyl-8-sulfanyl-octanamide;6-s-acetyldihydrolipoamide;S-acetyldihydrolipoamide;S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate;S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid
PW_C001174
S-Acyhp
203
4
808
Succinyl-CoA
HMDB0001022
Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).
604-98-8
C00091
439161
15380
3-METHYLBENZYLSUCCINYL-COA
388307
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O
C25H40N7O19P3S
InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1
VNOYUJKHFWYWIR-FZEDXVDRSA-N
4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid
867.607
867.131252359
-2.35
10
4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-4-oxobutanoic acid
0
-5
FDB022375
Coa s-(hydrogen succinate);Coa s-succinate;Coenzyme a s-(hydrogen succinate);Coenzyme a s-succinate;S-(hydrogen butanedioate;S-(hydrogen butanedioate) coa;S-(hydrogen butanedioate) coenzyme a;S-(hydrogen butanedioic acid;S-succinoylcoenzyme a;Suc-co-a;Suc-coa;Succ-coa;Succ-coenzyme a;Succ-s-coa;Succ-s-coenzyme a;Succ-s-coenzyme-a;Succ-coenzyme-a;Succino-1-yl-coenzyme a;Succinyl coa;Succinyl coenzyme a;Succinyl-s-coa;Succinyl-s-coenzyme a;Succinyl-s-coenzyme-a;Succinylcoenzyme-a;Succinylcoenzyme a
PW_C000808
Suc-CoA
233
4
1055
3
3669
2
5378
103
6039
155
6097
161
6485
178
7015
160
7361
163
7474
222
77140
133
78101
112
78576
132
80021
368
119978
406
120769
407
122014
124
122763
120
123365
119
124568
118
125358
479
126164
299
126306
481
126901
501
127868
206
913
(S)-Succinyldihydrolipoamide
HMDB0001177
(S)-Succinyldihydrolipoamide belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain (S)-Succinyldihydrolipoamide is considered to be a practically insoluble (in water) and relatively neutral molecule (S)-Succinyldihydrolipoamide has been primarily detected in urine. Within the cell, (S)-succinyldihydrolipoamide is primarily located in the membrane (predicted from logP), cytoplasm and adiposome (S)-Succinyldihydrolipoamide exists in all living organisms, ranging from bacteria to humans (S)-Succinyldihydrolipoamide can be biosynthesized from succinyl-CoA and dihydrolipoamide through the action of the enzyme acef. (S)-Succinyldihydrolipoamide is a metabolite (a product as well as a substrate) in glutamate degradation.
C01169
439425
17432
CPD0-341
388536
NC(=O)CCCC[C@H](CCS)SC(=O)CCC(O)=O
C12H21NO4S2
InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(7-8-18)19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)/t9-/m1/s1
RJCJWONCSKSHES-SECBINFHSA-N
4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid
307.429
307.091199545
-3.47
3
4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid
0
-1
FDB022467
S-succinyl-dihydrolipoamide;S-succinyldihydrolipoamide
PW_C000913
S-SucHp
6010
Glucose-6-phosphate isomerase
P0A6T1
Involved in glucose-6-phosphate isomerase activity. D-glucose 6-phosphate = D-fructose 6- phosphate.
pgi
b4025
AP009048
3
5.3.1.9
6212
108
8592
101
135637
609
135826
117
6114
Fructose-1,6-bisphosphatase class 2
P0A9C9
Involved in glycerol metabolic process. D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate.
glpX
b3925
AP009048
3
3.1.3.11
8593
101
6107
Fructose-1,6-bisphosphatase class 1
P0A993
Involved in phosphoric ester hydrolase activity. D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate.
fbp
b4232
AP009048
3
3.1.3.11
8594
101
7216
Uncharacterized protein yggF
P21437
Involved in glycerol metabolic process. Specific function unknown.
yggF
b2930
AP009048
3
3.1.3.11
6401
Phosphatase ybhA
P21829
Involved in catalytic activity. Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates pyridoxalphosphate and erythrose 4-phosphate.
ybhA
b0766
AP009048
3
3.1.3.74
7802
6-phosphofructokinase I
P0A796
3
8595
101
7803
6-phosphofructokinase II
P06999
pfkB
3
6109
Glyceraldehyde-3-phosphate dehydrogenase A
P0A9B2
gapA
b1779
AP009048
3
1.2.1.12
8596
101
6040
Phosphoglycerate kinase
P0A799
Involved in phosphoglycerate kinase activity. ATP + 3-phospho-D-glycerate = ADP + 3-phospho- D-glyceroyl phosphate.
pgk
b2926
AP009048
3
2.7.2.3
8597
101
7804
2,3-bisphosphoglycerate-independent phosphoglycerate mutase
P37689
gpmM
3
5961
147
7805
2,3-bisphosphoglycerate-dependent phosphoglycerate mutase
P62707
gpmA
3
6006
Enolase
P0A6P9
Involved in magnesium ion binding. Catalyzes the reversible conversion of 2- phosphoglycerate into phosphoenolpyruvate. It is essential for the degradation of carbohydrates via glycolysis. It is also a component of the RNA degradosome, a multi-enzyme complex involved in RNA processing and messenger RNA degradation. Its interaction with RNase E is important for the turnover of mRNA, in particular on transcripts encoding enzymes of energy-generating metabolic routes. Its presence in the degradosome is required for the response to excess phosphosugar. May play a regulatory role in the degradation of specific RNAs, such as ptsG mRNA, therefore linking cellular metabolic status with post-translational gene regulation.
eno
b2779
AP009048
3
4.2.1.11
6418
Phosphoenolpyruvate synthase
P23538
Involved in catalytic activity. Catalyzes the phosphorylation of pyruvate to phosphoenolpyruvate.
ppsA
b1702
AP009048
3
2.7.9.2
6216
Pyruvate kinase I
P0AD61
Involved in magnesium ion binding. ATP + pyruvate = ADP + phosphoenolpyruvate.
pykF
b1676
AP009048
3
2.7.1.40
5964
147
6399
Pyruvate kinase II
P21599
Involved in magnesium ion binding. ATP + pyruvate = ADP + phosphoenolpyruvate.
pykA
b1854
AP009048
3
2.7.1.40
5965
147
7738
Unknown
Unknown
3
5368
103
5762
140
5765
101
6213
108
7739
Unknown
Unknown
3
2.3.1.12
5369
103
7740
Unknown
Unknown
3
1.8.1.4
5370
103
7464
Phosphocarrier protein HPr
P0AA04
Involved in sugar:hydrogen symporter activity. General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III).
ptsH
b2415
AP009048
3
2.7.11.-
5702
108
6673
107
6674
117
8930
101
135644
610
6694
PTS system glucose-specific EIICB component
P69786
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity. The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration.
ptsG
b1101
AP009048
3
2.7.1.69
6203
109
135648
613
6693
Glucose-specific phosphotransferase enzyme IIA component
P69783
Involved in sugar:hydrogen symporter activity. The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport.
crr
b2417
AP009048
3
2.7.1.-
6152
109
8932
101
135649
613
6106
Fructose-bisphosphate aldolase class 1
P0A991
Involved in catalytic activity. D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
fbaB
b2097
AP009048
3
4.1.2.13
8598
101
6157
Fructose-bisphosphate aldolase class 2
P0AB71
Involved in catalytic activity. Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis.
fbaA
b2925
AP009048
3
4.1.2.13
6071
Triosephosphate isomerase
P0A858
Involved in catalytic activity. D-glyceraldehyde 3-phosphate = glycerone phosphate.
tpiA
b3919
AP009048
3
5.3.1.1
8599
101
10347
mannitol-1-phosphate 5-dehydrogenase
P09424
mltD
25
1.1.1.17
5826
PTS system mannitol-specific EIICBA component
P00550
Involved in transporter activity. The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannitol transport.
mtlA
b3599
AP009048
3
2.7.1.69; 2.7.1.-
6624
109
5903
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex
P06959
Involved in transferase activity, transferring acyl groups. The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). It contains multiple copies of three enzymatic components:pyruvate dehydrogenase (E1), dihydrolipoamide acetyltransferase (E2) and lipoamide dehydrogenase (E3).
aceF
b0115
AP009048
3
2.3.1.12
1342
phosphoglucose isomerase
3
PW_P001342
1565
6010
2
1345
fructose 1,6-bisphosphatase 2
3
PW_P001345
1568
6114
2
1344
Fructose-1,6-bisphosphatase 1
3
PW_P001344
1567
6107
4
1343
fructose-1,6-bisphosphatase
3
PW_P001343
1566
7216
2
1346
pyridoxal phosphatase/fructose 1,6-bisphosphatase
3
PW_P001346
1569
6401
1347
6-phosphofructokinase-1
3
PW_P001347
1570
7802
4
1571
7803
1349
Glyceraldehyde 3-phosphate dehydrogenase
3
PW_P001349
1574
6109
4
1350
phosphoglycerate kinase
3
PW_P001350
1575
6040
1351
2,3-bisphosphoglycerate-independent phosphoglycerate mutase
3
PW_P001351
1576
7804
1352
phosphoglycerate mutase
3
PW_P001352
1577
7805
2
1353
enolase
3
PW_P001353
1578
6006
2
1354
phosphoenolpyruvate synthetase
3
PW_P001354
1579
6418
2
1355
pyruvate kinase
3
PW_P001355
1580
6216
4
1581
6399
4
1276
Pyruvate dehydrogenase complex
3
PW_P001276
1470
7738
60
1471
7738
60
1472
7739
60
1473
7740
24
1549
HPr - phosphorylated
3
PW_P001549
1828
7464
1550
HPr
3
PW_P001550
1829
7464
3575
glucose PTS permease
3
PW_P003575
10413
6694
2
10414
6693
1348
fructose bisphosphate aldolase
3
PW_P001348
1572
6106
10
1573
6157
10
1536
triosephosphate isomerase
3
PW_P001536
1808
6071
2
3875
mannitol-1-phosphate 5-dehydrogenase
3
PW_P003875
10820
10347
3876
mannitol PTS permease
3
PW_P003876
10821
5826
2
3901
AceF
3
PW_P003901
10867
5903
2633
false
PW_R002633
Right
10293
79
1
Compound
false
10294
414
1
Compound
false
10295
833
1
Compound
false
10296
1034
1
Compound
false
10297
40034
1
Compound
false
2626
1347
2636
false
PW_R002636
Right
10306
983
1
Compound
false
10307
1034
1
Compound
true
10308
414
1
Compound
true
10309
644
1
Compound
false
2629
1350
2.7.2.3
2638
false
PW_R002638
Right
10312
644
1
Compound
false
10313
1870
1
Compound
false
2631
1352
2639
false
PW_R002639
Right
10314
1870
1
Compound
false
10315
180
1
Compound
false
10316
1420
1
Compound
false
2632
1353
4.2.1.11
2641
false
PW_R002641
Right
10324
180
1
Compound
false
10325
1034
1
Compound
false
10326
40034
1
Compound
false
10327
414
1
Compound
false
10328
164
1
Compound
false
2634
1355
2.7.1.40
2574
false
PW_R002574
Right
10015
164
1
Compound
false
10016
1099
1
Compound
true
10017
721
1
Compound
true
10018
940
1
Compound
false
10019
1316
1
Compound
true
10020
1144
1
Compound
true
2542
1276
1.2.4.1
2936
false
PW_R002936
Both
11671
869
1
Compound
false
11672
1134
1
Compound
false
2902
1536
5.3.1.1
5148
false
PW_R005148
Both
20813
79
1
Compound
false
20814
1144
1
Compound
false
20815
40034
1
Compound
false
20816
721
1
Compound
false
20817
1176
1
Compound
false
5121
3875
1.1.1.17
5172
false
PW_R005172
Both
20922
940
1
Compound
false
20923
782
1
Compound
false
20924
1099
1
Compound
false
20925
1174
1
Compound
false
5143
3901
2.3.1.12
5173
false
PW_R005173
Right
20926
808
1
Compound
false
20927
782
1
Compound
false
20928
1099
1
Compound
false
20929
913
1
Compound
false
5144
3901
2637
false
PW_R002637
Right
10310
644
1
Compound
false
10311
1870
1
Compound
false
2630
1351
2640
false
PW_R002640
Right
10317
180
1
Compound
false
10318
32
1
Compound
false
10319
1104
1
Compound
false
10320
40034
2
Compound
false
10321
414
1
Compound
false
10322
1420
1
Compound
false
10323
164
1
Compound
false
2633
1354
2.7.9.2
2634
false
PW_R002634
Both
10298
833
1
Compound
false
10299
869
1
Compound
false
13768
1134
1
Compound
false
2627
1348
4.1.2.13
2632
false
PW_R002632
Right
10289
79
1
Compound
false
10290
1104
1
Compound
false
10291
833
1
Compound
false
10292
1420
1
Compound
false
2622
1343
3.1.3.11
2623
1344
3.1.3.11
2624
1345
3.1.3.11
2625
1346
3.1.3.74
2635
false
PW_R002635
Right
10300
869
1
Compound
false
10301
721
1
Compound
false
10302
1104
1
Compound
false
10303
983
1
Compound
false
10304
1144
1
Compound
false
10305
40034
1
Compound
false
2628
1349
1.2.1.12
2631
false
PW_R002631
Right
10287
1906
1
Compound
false
10288
79
1
Compound
false
2621
1342
5.3.1.9
138
PW_RCT000138
Right
814
138
395
Compound
1
107
815
138
1549
ProteinComplex
1
108
816
138
1906
Compound
1
108
817
138
1550
ProteinComplex
1
108
138
171
PW_RCT000171
Right
1016
171
611
Compound
1
107
1017
171
1549
ProteinComplex
1
108
1018
171
1176
Compound
1
108
1019
171
1550
ProteinComplex
1
108
171
14159
79
3
false
1197
1085
10
regular
100
110
14160
1104
46
false
1708
1178
10
regular
44
43
14162
1420
49
false
2006
1151
10
regular
78
78
14163
414
42
false
1792
855
10
regular
50
30
14164
833
3
false
2195
1085
10
regular
100
110
14165
1034
43
false
2090
975
10
regular
50
30
14166
40034
55
false
2110
806
10
regular
78
78
14168
721
59
false
2111
1690
10
regular
50
30
14169
1104
46
false
2111
1548
10
regular
44
43
14170
983
3
false
1451
1585
10
regular
100
110
14171
1144
60
false
1756
1555
10
regular
50
30
14172
40034
55
false
1721
1691
10
regular
78
78
14173
1034
43
false
1356
1660
10
regular
50
30
14174
414
42
false
1021
1565
10
regular
50
30
14175
644
3
false
846
1580
10
regular
100
120
14177
1870
3
false
896
2035
10
regular
100
110
14178
180
3
false
1586
2035
10
regular
100
110
14179
1420
49
false
1356
2126
10
regular
78
78
14180
32
44
false
1854
2275
10
regular
50
30
14181
1104
46
false
1764
2273
10
regular
44
43
14182
40034
55
false
1803
2381
10
regular
78
78
14183
414
42
false
2171
2260
10
regular
50
30
14184
1420
49
false
2161
2411
10
regular
78
78
14186
1034
43
false
1818
2130
10
regular
50
30
14187
40034
55
false
1808
1951
10
regular
78
78
14188
414
42
false
2177
2020
10
regular
50
30
14189
164
3
false
2347
2040
10
regular
100
100
14190
1099
85
false
2497
2140
10
regular
50
30
14191
721
59
false
2487
2015
10
regular
50
30
14192
940
3
false
2698
2740
10
regular
100
100
14193
1316
52
false
2833
2271
10
regular
78
78
14194
1144
60
false
2596
2275
10
regular
50
30
19895
1906
107
3
false
147
1085
10
regular
100
110
19896
1906
108
3
false
632
1085
10
regular
100
110
19947
1134
3
false
2645
1385
10
regular
100
110
19948
869
3
false
2330
1580
10
regular
100
120
61353
1144
60
false
1152
922
10
regular
50
30
61354
40034
55
false
1298
902
10
regular
78
78
61355
721
59
false
1147
726
10
regular
50
30
61356
1176
3
false
1197
586
10
regular
100
110
61357
611
107
3
false
1197
198
10
regular
100
100
61607
782
3
false
2198
2740
10
regular
100
100
61608
1099
85
false
2420
2535
10
regular
50
30
61609
1174
3
false
2575
2495
10
regular
100
110
61614
808
3
false
1983
2640
10
regular
100
100
61615
1099
85
false
1630
2860
10
regular
50
30
61616
913
3
false
1450
2735
10
regular
100
110
7377
6010
101
6
false
892
1100
8
subunit
regular
160
80
7378
6114
101
6
false
1786
1002
8
subunit
regular
160
80
7379
6107
101
8
false
1716
1045
8
subunit
regular
140
85
7380
7216
6
false
1851
1052
8
subunit
regular
160
80
7381
6401
2
false
1781
1107
8
subunit
regular
150
70
7382
7802
101
8
false
1939
830
8
subunit
regular
140
85
7383
7803
2
false
1879
882
8
subunit
regular
150
70
7386
6109
101
8
false
1855
1600
8
subunit
regular
140
85
7387
6040
101
2
false
1103
1607
8
subunit
regular
150
70
7388
7804
2
false
621
1855
8
subunit
regular
150
70
7389
7805
6
false
816
1850
8
subunit
regular
160
80
7390
6006
6
false
1146
2052
8
subunit
regular
160
80
7391
6418
6
false
1947
2300
8
subunit
regular
160
80
7392
6216
8
false
1999
2000
8
subunit
regular
140
85
7393
6399
8
false
1954
2050
8
subunit
regular
140
85
7394
7738
136
false
2664
1895
8
subunit
regular
175
155
7395
7738
136
false
2569
1950
8
subunit
regular
175
155
7396
7739
136
false
2749
1960
8
subunit
regular
175
155
7397
7740
136
false
2654
2010
8
subunit
regular
175
155
9525
7464
108
2
false
447
1260
8
subunit
regular
150
70
9526
7464
108
2
false
447
955
8
subunit
regular
150
70
9527
6694
109
77
false
407
1100
8
subunit
regular
160
80
9528
6693
109
76
false
292
1105
8
subunit
regular
150
70
9563
6106
101
136
false
2205
1360
8
subunit
regular
175
155
9564
6157
136
false
2100
1315
8
subunit
regular
175
155
9565
6071
101
6
false
2615
1600
8
subunit
regular
160
80
28590
10347
2
false
1172
806
8
subunit
regular
150
70
28591
7464
108
2
false
972
508
8
subunit
regular
150
70
28592
7464
108
2
false
1372
506
8
subunit
regular
150
70
28593
5826
109
77
false
1167
336
8
subunit
regular
160
80
28692
5903
2
false
2443
2620
8
subunit
regular
150
70
28694
5903
2
false
1773
2757
8
subunit
regular
150
70
5949
1342
533
7280
7377
5950
1345
533
7281
7378
5951
1344
533
7282
7379
5952
1343
533
7283
7380
5953
1346
533
7284
7381
5954
1347
533
7285
7382
7286
7383
5956
1349
533
7289
7386
5957
1350
533
7290
7387
5958
1351
533
7291
7388
5959
1352
533
7292
7389
5960
1353
533
7293
7390
5961
1354
533
7294
7391
5962
1355
533
7295
7392
7296
7393
5963
1276
533
7297
7394
7298
7395
7299
7396
7300
7397
7582
1549
533
108
9335
9525
7583
1550
533
108
9336
9526
7584
3575
533
109
9337
9527
9338
9528
7610
1348
533
9373
9563
9374
9564
7611
1536
533
9375
9565
24086
3875
533
28278
28590
24087
1549
533
108
28279
28591
24088
1550
533
108
28280
28592
24089
3876
533
109
28281
28593
24149
3901
533
28380
28692
24151
3901
533
28382
28694
21873
M1297 1140 C1394 1140 1590 1140 1651 1141 C1651 1068 1651 998 1653 915 C1754 915 1812 915 1879 917
5
false
18
21874
M1817 885 C1817 905 1834 917 1879 917
5
false
18
21875
M2245 1085 C2246 998 2246 1010 2247 917 C2189 917 2115 917 2029 917
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21876
M2115 975 C2100 939 2107 917 2029 917
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21877
M2149 884 C2136 908 2065 916 2029 917
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21886
M1451 1640 C1389 1639 1328 1644 1253 1642
5
false
18
21887
M1356 1675 C1300 1677 1256 1617 1253 1642
5
false
18
21888
M1046 1595 C1041 1624 1049 1641 1103 1642
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21889
M946 1640 C1009 1640 1047 1641 1103 1642
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21892
M896 1700 C895 1815 896 1757 896 1850
5
false
18
21893
M896 2090 C896 2055 897 1954 896 1930
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21894
M996 2090 C1076 2091 1082 2091 1146 2092
5
false
18
21895
M1586 2090 C1531 2091 1414 2092 1306 2092
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21896
M1395 2126 C1394 2095 1357 2092 1306 2092
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21904
M1686 2090 C1821 2090 1872 2090 1954 2090
5
false
18
21905
M1843 2130 C1849 2103 1905 2089 1954 2090
5
false
18
21906
M1847 2029 C1847 2070 1869 2090 1954 2090
5
false
18
21907
M2202 2050 C2187 2082 2168 2090 2094 2090
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21908
M2347 2090 C2241 2090 2227 2090 2094 2090
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21909
M2447 2090 C2513 2090 2572 2091 2659 2090
5
false
18
21910
M2522 2140 C2521 2105 2603 2091 2659 2090
5
false
18
21911
M2512 2045 C2517 2087 2582 2092 2659 2090
5
false
18
21912
M2748 2740 C2748 2710 2744 2195 2744 2165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21913
M2833 2310 C2778 2308 2746 2260 2744 2165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
21914
M2646 2290 C2725 2275 2744 2195 2744 2165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
29761
M247 1140 C283 1141 248 1140 292 1140
5
false
18
29762
M632 1140 C600 1140 595 1140 567 1140
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
29763
M447 1295 C401 1291 364 1271 367 1175
5
false
18
false
false
29764
M447 990 C394 989 377 1006 367 1105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
false
false
29837
M2430 1640 C2535 1640 2533 1639 2615 1640
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
29838
M2695 1495 C2695 1525 2695 1570 2695 1600
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88130
M1247 1085 C1247 1012 1248 967 1247 876
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
88131
M1202 937 C1236 937 1248 924 1247 876
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
88132
M1298 941 C1276 939 1250 911 1247 876
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
88133
M1197 741 C1236 748 1247 763 1247 806
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
88134
M1247 696 C1248 744 1247 728 1247 806
5
false
18
true
M 25.946855044164835 398.261556296296 L 11 397 L 17.380887721185843 410.5751343230783
false
88135
M1247 298 C1247 331 1247 292 1247 336
5
false
18
88136
M1247 586 C1247 526 1247 485 1247 416
5
false
18
true
M 877.6135217108315 398.261556296296 L 862.6666666666666 397 L 869.0475543878524 410.5751343230783
false
88137
M1047 508 C1047 469 1084 378 1167 376
5
false
18
88138
M1447 506 C1448 439 1398 375 1327 376
5
false
18
true
M 877.6135217108315 398.261556296296 L 862.6666666666666 397 L 869.0475543878524 410.5751343230783
false
88435
M2698 2790 C2578 2790 2517 2742 2518 2690
5
false
18
true
M 672.2801883774982 4247.5948896296295 L 657.3333333333334 4246.333333333333 L 663.7142210545192 4259.908467656412
false
88436
M2298 2790 C2360 2789 2517 2778 2518 2690
5
false
18
true
M 672.2801883774982 4247.5948896296295 L 657.3333333333334 4246.333333333333 L 663.7142210545192 4259.908467656412
false
88437
M2470 2550 C2513 2552 2518 2590 2518 2620
5
false
18
true
M 672.2801883774982 4247.5948896296295 L 657.3333333333334 4246.333333333333 L 663.7142210545192 4259.908467656412
false
88438
M2575 2550 C2548 2551 2515 2554 2518 2620
5
false
18
true
M 672.2801883774982 4247.5948896296295 L 657.3333333333334 4246.333333333333 L 663.7142210545192 4259.908467656412
false
88443
M2033 2740 C2031 2775 2038 2791 1923 2792
5
false
18
88444
M2198 2790 C2130 2791 2052 2791 1923 2792
5
false
18
88445
M1655 2860 C1654 2820 1697 2791 1773 2792
5
false
18
true
M 672.2801883774982 4183.5948896296295 L 657.3333333333334 4182.333333333333 L 663.7142210545192 4195.908467656412
false
88446
M1550 2790 C1639 2790 1702 2791 1773 2792
5
false
18
true
M 672.2801883774982 4183.5948896296295 L 657.3333333333334 4182.333333333333 L 663.7142210545192 4195.908467656412
false
2945907
M1247 1195 C1247 1276 1248 1250 1247 1307
5
false
18
true
M 1302.4008505046538 863.5608704974252 L 1290 872 L 1303.5089257873833 878.5198868142758
false
2949458
M2695 1385 C2696 1336 2696 1385 2695 1305
5
false
18
2949627
M846 1640 C778 1641 712 1641 696 1641 C696 1741 696 1806 696 1855
5
false
18
2949628
M896 2090 C886 2090 710 2090 697 2090 C695 2033 696 1964 696 1925
5
false
18
true
M 236.00961894323342 2457.5 L 249 2450 L 236.00961894323342 2442.5
false
2949845
M896 1580 C897 1486 897 1620 896 1510
5
false
18
2950134
M1686 2090 C1686 2140 1687 2234 1685 2340 C1759 2339 1896 2341 1947 2340
5
false
18
2950135
M1879 2305 C1878 2330 1888 2341 1947 2340
5
false
18
2950136
M1786 2316 C1792 2340 1885 2339 1947 2340
5
false
18
2950137
M1842 2381 C1843 2347 1915 2341 1947 2340
5
false
18
2950138
M2196 2290 C2191 2323 2179 2340 2107 2340
5
false
18
true
M 805.9468550441649 3594.261556296296 L 791 3593 L 797.3808877211858 3606.575134323078
false
2950139
M2200 2411 C2201 2371 2190 2341 2107 2340
5
false
18
true
M 805.9468550441649 3594.261556296296 L 791 3593 L 797.3808877211858 3606.575134323078
false
2950140
M2347 2090 C2346 2196 2346 2217 2346 2339 C2240 2341 2209 2340 2107 2340
5
false
18
true
M 805.9468550441649 3594.261556296296 L 791 3593 L 797.3808877211858 3606.575134323078
false
false
false
2950256
M2748 2840 C2748 2896 2748 2853 2748 2890
5
false
18
true
M 1648.0096189432334 4717.5 L 1661 4710 L 1648.0096189432334 4702.5
false
2950412
M2295 1140 C2297 1169 2295 1397 2295 1367
5
false
18
true
M 1017.9468550441649 1567.261556296296 L 1003 1566 L 1009.3808877211858 1579.5751343230784
false
2950413
M2380 1580 C2382 1550 2380 1410 2380 1440
5
false
18
true
M 1017.9468550441649 1567.261556296296 L 1003 1566 L 1009.3808877211858 1579.5751343230784
false
2950414
M2645 1440 C2566 1441 2442 1440 2380 1440
5
false
18
true
M 1017.9468550441649 1567.261556296296 L 1003 1566 L 1009.3808877211858 1579.5751343230784
false
2950523
M1297 1140 C1476 1141 1743 1142 1781 1142
5
false
18
2950524
M1752 1199.5 C1823 1200.5 1779 1105 1781 1142
5
false
18
2950525
M2195 1140 C2115 1140 2050 1141 1931 1142
5
false
18
true
M 921.9468550441649 1382.261556296296 L 907 1381 L 913.3808877211858 1394.5751343230784
false
2950526
M2006 1190 C2044 1189 1932 1211 1931 1142
5
false
18
true
M 921.9468550441649 1382.261556296296 L 907 1381 L 913.3808877211858 1394.5751343230784
false
2950791
M2330 1640 C2250 1640 2072 1640 1995 1640
5
false
18
2950792
M2136 1690 C2136 1675 2086 1639 1995 1640
5
false
18
2950793
M2133 1591 C2128 1617 2077 1640 1995 1640
5
false
18
2950794
M1551 1640 C1593 1640 1819 1640 1855 1640
5
false
18
true
M 830.9468550441649 1961.261556296296 L 816 1960 L 822.3808877211858 1973.5751343230784
false
2950795
M1781 1585 C1780 1605 1811 1639 1855 1640
5
false
18
true
M 830.9468550441649 1961.261556296296 L 816 1960 L 822.3808877211858 1973.5751343230784
false
2950796
M1760 1691 C1761 1652 1815 1640 1855 1640
5
false
18
true
M 830.9468550441649 1961.261556296296 L 816 1960 L 822.3808877211858 1973.5751343230784
false
3658058
M732 1140 C762 1140 862 1140 892 1140
5
false
18
3658059
M1197 1140 C1167 1140 1082 1140 1052 1140
5
false
18
true
M 269.94685504416486 1002.261556296296 L 255 1001 L 261.38088772118584 1014.5751343230784
false
3799
533
2633
12803
14159
21873
Left
12804
14163
21874
Left
12805
14164
21875
Right
12806
14165
21876
Right
12807
14166
21877
Right
4018
2626
5954
3802
533
2636
12816
14170
21886
Left
12817
14173
21887
Left
12818
14174
21888
Right
12819
14175
21889
Right
4021
2629
5957
3804
533
2638
12822
14175
21892
Left
12823
14177
21893
Right
4023
2631
5959
3805
533
2639
12824
14177
21894
Left
12825
14178
21895
Right
12826
14179
21896
Right
4024
2632
5960
3807
533
2641
12834
14178
21904
Left
12835
14186
21905
Left
12836
14187
21906
Left
12837
14188
21907
Right
12838
14189
21908
Right
4026
2634
5962
3808
533
2574
12839
14189
21909
Left
12840
14190
21910
Left
12841
14191
21911
Left
12842
14192
21912
Right
12843
14193
21913
Right
12844
14194
21914
Right
4027
2542
5963
5265
533
2936
18878
19948
29837
Left
18879
19947
29838
Right
5421
2902
7611
17926
533
5148
68982
14159
88130
Left
68983
61353
88131
Left
68984
61354
88132
Left
68985
61355
88133
Right
68986
61356
88134
Right
18129
5121
24086
17965
533
5172
69161
14192
88435
Left
69162
61607
88436
Left
69163
61608
88437
Right
69164
61609
88438
Right
18165
5143
24149
17967
533
5173
69169
61614
88443
Left
69170
61607
88444
Left
69171
61615
88445
Right
69172
61616
88446
Right
18167
5144
24151
654497
533
2637
117
2644417
14175
2949627
Left
2644418
14177
2949628
Right
612323
2630
5958
654603
533
2640
101
2644860
14178
2950134
Left
2644861
14180
2950135
Left
2644862
14181
2950136
Left
2644863
14182
2950137
Left
2644864
14183
2950138
Right
2644865
14184
2950139
Right
2644866
14189
2950140
Right
612429
2633
5961
654660
533
2634
117
2645103
14164
2950412
Left
2645104
19948
2950413
Right
2645105
19947
2950414
Right
612486
2627
7610
654684
533
2632
117
2645202
14159
2950523
Left
2645203
14160
2950524
Left
2645204
14164
2950525
Right
2645205
14162
2950526
Right
612510
2624
5950
612511
2622
5952
612512
2623
5951
612513
2625
5953
654740
533
2635
117
2645437
19948
2950791
Left
2645438
14168
2950792
Left
2645439
14169
2950793
Left
2645440
14170
2950794
Right
2645441
14171
2950795
Right
2645442
14172
2950796
Right
612569
2628
5956
797207
533
2631
101
3222251
19896
3658058
Left
3222252
14159
3658059
Right
752881
2621
5949
244
138
533
1393
19895
29761
Left
1394
19896
29762
Right
39
7582
29763
Left
40
7583
29764
Right
247
7584
172
381
171
533
2130
61357
88135
Left
2131
61356
88136
Right
89
24087
88137
Left
90
24088
88138
Right
387
24089
205
82797
83303
533
14
false
1172
1307
16
regular
79907
14159
2945907
Left
82944
83449
533
14
false
2620
1235
16
regular
80053
19947
2949458
Right
82960
83464
533
14
false
821
1440
16
regular
80069
14175
2949845
Left
82978
83484
533
14
false
2673
2890
16
regular
80087
14192
2950256
Left
186250
557
2200
1.6
1.6
0
2
92
479
481
961
M370 476 C370 426 420 376 470 376 C1198 376 2146 376 2874 376 C2924 376 2974 426 2974 476 C2974 1219 2974 2184 2974 2927 C2974 2977 2924 3027 2874 3027 C2146 3027 1198 3027 470 3027 C420 3027 370 2977 370 2927 C370 2184 370 1219 370 476
1
true
6
2604.0
2651.0
962
M125 225 C125 175 175 125 225 125 C1103 125 2243 125 3121 125 C3171 125 3221 175 3221 225 C3221 1120 3221 2284 3221 3179 C3221 3229 3171 3279 3121 3279 C2243 3279 1103 3279 225 3279 C175 3279 125 3229 125 3179 C125 2284 125 1120 125 225
1
true
6
3096.0
3154.0