557
Pathway
Ascorbate Metabolism
E. coli is able to utilize L-ascorbate (vitamin C) as the sole source of carbon under anaerobic and aerobic conditions.
Ascorbic acid in the cytoplasm is processed through a spontaneous reaction with a hydrogen ion and hydrogen peroxide, producing water, dehydroascorbic acid and ascorbic acid. Dehydroascorbic acid reacts with water spontaneously producing an isomer, dehydroascorbate (bicyclic form). The compound then loses a hydrogen ion resulting in a 2,3-Diketo-L-gulonate. This compound is then reduced through a NADH dependent 2,3 diketo-L-gulonate reductase, releasing a NAD and 3-Dehydro-L-gulonate.This compound is phosphorylated through an ATP mediated L-xylulose/3-keto-L-gulonate kinase resulting in an ADP, hydrogen ion and a 3-Keto-L-gulonate 6 phosphate.
L-ascorbate can also be imported and converted to L-ascorbate-6-phosphate by the L-ascorbate PTS transporter. L-ascorbate-6-phosphate reacts with a probable L-ascorbate-6-phosphate lactonase ulaG, resulting in a 3-keto-L-gulonate 6-phosphate.
The compound 3-keto-L-gulonate 6-phosphate can be processed aerobically or anaerobically.
Aerobic:
3-keto-L-gulonate 6-phosphate is decarboxylated by a 3-keto-L-gulonate-6-phosphate decarboxylase ulaD, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by L-ribulose-5-phosphate 3-epimerase ulaE, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase ulaF resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway.
Anaerobic:
3-keto-L-gulonate 6-phosphate is decarboxylated by 3-keto-L-gulonate 6-phosphate decarboxylase sgbH, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by predicted L-xylulose 5-phosphate 3-epimerase, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway.
Expression of the ula regulon is regulated by the L-ascorbate 6-phosphate-binding repressor UlaR and by cAMP-CRP.
Under aerobic conditions, metabolism of L-ascorbate is hindered by the special reactivity and toxicity of this compound in the presence of oxygen.
Metabolic
PW000793
Center
PathwayVisualizationContext1080
2500
3350
#000099
PathwayVisualization541
557
Ascorbate Metabolism
E. coli is able to utilize L-ascorbate (vitamin C) as the sole source of carbon under anaerobic and aerobic conditions.
Ascorbic acid in the cytoplasm is processed through a spontaneous reaction with a hydrogen ion and hydrogen peroxide, producing water, dehydroascorbic acid and ascorbic acid. Dehydroascorbic acid reacts with water spontaneously producing an isomer, dehydroascorbate (bicyclic form). The compound then loses a hydrogen ion resulting in a 2,3-Diketo-L-gulonate. This compound is then reduced through a NADH dependent 2,3 diketo-L-gulonate reductase, releasing a NAD and 3-Dehydro-L-gulonate.This compound is phosphorylated through an ATP mediated L-xylulose/3-keto-L-gulonate kinase resulting in an ADP, hydrogen ion and a 3-Keto-L-gulonate 6 phosphate.
L-ascorbate can also be imported and converted to L-ascorbate-6-phosphate by the L-ascorbate PTS transporter. L-ascorbate-6-phosphate reacts with a probable L-ascorbate-6-phosphate lactonase ulaG, resulting in a 3-keto-L-gulonate 6-phosphate.
The compound 3-keto-L-gulonate 6-phosphate can be processed aerobically or anaerobically.
Aerobic:
3-keto-L-gulonate 6-phosphate is decarboxylated by a 3-keto-L-gulonate-6-phosphate decarboxylase ulaD, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by L-ribulose-5-phosphate 3-epimerase ulaE, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase ulaF resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway.
Anaerobic:
3-keto-L-gulonate 6-phosphate is decarboxylated by 3-keto-L-gulonate 6-phosphate decarboxylase sgbH, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by predicted L-xylulose 5-phosphate 3-epimerase, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway.
Expression of the ula regulon is regulated by the L-ascorbate 6-phosphate-binding repressor UlaR and by cAMP-CRP.
Under aerobic conditions, metabolism of L-ascorbate is hindered by the special reactivity and toxicity of this compound in the presence of oxygen.
Metabolic
3
93024
657
SubPathway
91144
691
Compound
117
2060
11741871
Yew WS, Gerlt JA: Utilization of L-ascorbate by Escherichia coli K-12: assignments of functions to products of the yjf-sga and yia-sgb operons. J Bacteriol. 2002 Jan;184(1):302-6.
557
Pathway
2061
12644495
Zhang Z, Aboulwafa M, Smith MH, Saier MH Jr: The ascorbate transporter of Escherichia coli. J Bacteriol. 2003 Apr;185(7):2243-50.
557
Pathway
2062
14996803
Campos E, Baldoma L, Aguilar J, Badia J: Regulation of expression of the divergent ulaG and ulaABCDEF operons involved in LaAscorbate dissimilation in Escherichia coli. J Bacteriol. 2004 Mar;186(6):1720-8.
557
Pathway
2063
18844374
Garces F, Fernandez FJ, Gomez AM, Perez-Luque R, Campos E, Prohens R, Aguilar J, Baldoma L, Coll M, Badia J, Vega MC: Quaternary structural transitions in the DeoR-type repressor UlaR control transcriptional readout from the L-ascorbate utilization regulon in Escherichia coli. Biochemistry. 2008 Nov 4;47(44):11424-33. doi: 10.1021/bi800748x. Epub 2008 Oct 10.
557
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
110
Bacillus velezensis MRC5958
492670
Prokaryote
Velezensis
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
11
Extracellular Space
GO:0005615
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
27
Peroxisome Membrane
GO:0005778
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
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
8
5
1
1
PW_BS000008
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
4
3
1
1
PW_BS000004
3
2
1
1
PW_BS000003
14
10
1
PW_BS000014
13
1
2
1
PW_BS000013
15
11
1
PW_BS000015
28
1
16
1
1
PW_BS000028
10
1
7
1
1
PW_BS000010
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
18
13
1
1
PW_BS000018
2
1
1
1
PW_BS000002
31
1
5
1
1
PW_BS000031
49
7
1
1
PW_BS000049
54
1
3
1
5
PW_BS000054
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
22
14
1
1
PW_BS000022
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
17
12
1
1
PW_BS000017
29
1
1
1
PW_BS000029
70
28
5
1
1
PW_BS000070
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
94
3
PW_BS000094
103
3
3
1
PW_BS000103
105
11
3
PW_BS000105
111
5
12
1
PW_BS000111
113
6
12
1
PW_BS000113
112
2
12
1
PW_BS000112
110
2
3
1
PW_BS000110
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
130
13
12
1
PW_BS000130
114
11
12
PW_BS000114
129
1
5
12
1
PW_BS000129
135
5
17
1
PW_BS000135
118
1
17
1
PW_BS000118
108
1
3
PW_BS000108
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
101
5
3
1
PW_BS000101
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
107
31
3
PW_BS000107
95
1
7
2
1
PW_BS000095
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
163
2
18
1
PW_BS000163
159
24
PW_BS000159
1
1
PW_BS000001
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
117
1
3
1
PW_BS000117
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
205
5
6
1
PW_BS000024
207
6
6
1
PW_BS000024
206
2
6
1
PW_BS000024
211
10
18
PW_BS000024
213
7
18
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
222
3
4
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
170
18
PW_BS000170
225
35
4
1
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
164
4
PW_BS000164
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
249
13
4
1
PW_BS000024
227
34
4
1
PW_BS000024
65
11
1
PW_BS000065
290
5
49
1
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
300
13
10
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
223
12
4
1
PW_BS000024
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
315
1
23
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
293
4
1
PW_BS000024
253
5
4
1
PW_BS000024
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
336
1
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
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
368
3
60
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
384
12
5
1
PW_BS000100
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
398
7
17
1
PW_BS000113
232
40
3
PW_BS000024
122
5
5
1
PW_BS000122
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
408
4
5
1
PW_BS000115
124
1
5
1
PW_BS000124
412
1
2
5
PW_BS000115
405
10
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
429
1
5
1
PW_BS000115
121
12
17
1
PW_BS000121
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
382
14
5
1
PW_BS000100
436
25
5
PW_BS000115
120
3
17
1
PW_BS000120
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
446
1
2
17
PW_BS000115
376
10
17
PW_BS000053
137
11
17
PW_BS000137
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
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
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
1
PW_BS000113
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
482
4
10
1
PW_BS000115
299
1
10
1
PW_BS000024
483
11
10
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
495
7
10
1
PW_BS000115
484
14
10
1
PW_BS000115
480
12
10
1
PW_BS000115
501
3
6
1
PW_BS000115
502
4
6
1
PW_BS000115
388
1
6
1
PW_BS000112
208
11
6
PW_BS000024
209
10
6
PW_BS000024
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
395
13
6
1
PW_BS000113
513
1
7
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
23
15
1
1
PW_BS000023
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
109
32
3
PW_BS000109
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
47
19
1
4
PW_BS000047
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
304
1
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
326
8
12
PW_BS000028
416
8
5
PW_BS000115
452
8
17
PW_BS000115
488
8
10
PW_BS000115
505
8
6
PW_BS000115
610
1
110
PW_BS000503
40859
L-ascorbate 6-phosphate
L-Ascorbate 6-phosphate belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. L-Ascorbate 6-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). An organophosphate oxoanion that is the trianion formed from L-ascorbic acid 6-phosphate by deprotonation of the 3-hydroxy group and of both hydroxy groups of the phosphate function
61698
[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O
C6H6O9P
InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1
KIENGQUGHPTFGC-JLAZNSOCSA-K
(2R)-4-hydroxy-2-[(1S)-1-hydroxy-2-(phosphonatooxy)ethyl]-5-oxo-2,5-dihydrofuran-3-olate
253.08
252.976589511
-0.74
2
L-ascorbate 6-phosphate
-3
-3
L-ascorbate-6-phosphate(3−),l-ascorbate-6-phosphate,l-ascorbate 6-phosphate,l-ascorbate 6-phosphate
PW_C040859
LA6P
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
40860
3-keto-L-gulonate 6-phosphate
6-(Hydrogen phosphonatooxy)-2,4,5-trihydroxy-3-oxohexanoate is soluble (in water) and a moderately acidic compound (based on its pKa). 3-Keto-L-gulonate 6-phosphate has the chemical formula C6H9O10P, and an average molecular weight of 272.103. 3-Keto-L-gulonate 6-phosphate is involved in the Ascorbate Metabolism Pathway.
58774
OC(COP([O-])([O-])=O)C(O)C(=O)C(O)C(O)=O
C6H9O10P
InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/p-2
BDUIIKXSXFDPEC-UHFFFAOYSA-L
2,4,5-trihydroxy-3-oxo-6-(phosphonatooxy)hexanoic acid
272.103
271.994430648
-0.84
4
2,4,5-trihydroxy-3-oxo-6-(phosphonatooxy)hexanoic acid
-2
-3
3-keto-l-gulonate 6-p, 3-keto-l-gulonate-6-phosphate, 3-dehydro-l-gulonate-6-phosphate
PW_C040860
3KLG6P
2724
3-Dehydro-L-gulonate
HMDB0006334
3-Dehydro-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 3-Dehydro-L-gulonate is the 4th to last step in the synthesis of D-Xylulose 5-phosphate and is converted from 2,3-Diketo-L-gulonate via the enzyme 3-dehydro-L-gulonate 2-dehydrogenase (EC 1.1.1.130). It is then converted to 3-Dehydro-L-gulonate 6-phosphate via the enzyme L-xylulokinase (EC 2.7.1.53).
C00618
439273
16142
388406
OC[C@H](O)[C@@H](O)C(=O)[C@H](O)C(O)=O
C6H10O7
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,5,7-9,11H,1H2,(H,12,13)/t2-,3+,5-/m0/s1
WTAHRPBPWHCMHW-LWKDLAHASA-N
(2S,4R,5S)-2,4,5,6-tetrahydroxy-3-oxohexanoic acid
194.1394
194.042652674
-0.27
5
3-dehydro-L-gulonic acid
0
-1
FDB023894
3-dehydro-l-gulonic acid;L-xylo-hex-3-ulosonic acid;3-dehydro-l-gulonate
PW_C002724
3DLG
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
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
2783
2,3-Diketo-L-gulonate
HMDB0006511
2,3-Diketo-L-gulonate, also known as 2,3-diketo-L-gulonic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2,3-Diketo-L-gulonate is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, 2,3-diketo-L-gulonate is primarily located in the cytoplasm. 2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-).
3445-22-5
C04575
53477844
15622
2,3-diketo-l-gulonate
OC[C@H](O)C(O)C(=O)C(=O)C(O)=O
C6H8O7
InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3?/m0/s1
GJQWCDSAOUMKSE-SCQFTWEKSA-N
(5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
192.1235
192.02700261
-0.51
4
(5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
0
-1
FDB023950
(4r,5s)-4,5,6-trihydroxy-2,3-dioxohexanoate;(4r,5s)-4,5,6-trihydroxy-2,3-dioxohexanoic acid;2,3-diketo-l gulonic acid;2,3-diketo-l-gulonate;2,3-diketogulonic acid;Diketogulonic acid;L-threo-2,3-hexodiulosonic acid;L-threo-hexo-2,3-diulosonic acid
PW_C002783
2,3-DkG
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
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
40861
dehydroascorbate (bicyclic form)
5-(1,2-Dihydroxyethyl)-2,3,4(5H)-furantrione, also known as dehydroascorbate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-(1,2-Dihydroxyethyl)-2,3,4(5H)-furantrione is soluble (in water) and a moderately acidic compound (based on its pKa). 5-(1,2-Dihydroxyethyl)-2,3,4(5H)-furantrione can be biosynthesized from ascorbic acid..
17242
[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO
C6H6O6
InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1
SBJKKFFYIZUCET-DUZGATOHSA-N
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
174.1082
174.016437924
0.04
2
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
0
-1
Dehydroascorbate monohydrate
PW_C040861
DHABcyc
977
Dehydroascorbic acid
HMDB0001264
Dehydroascorbic acid is the oxidized form of vitamin C. Reduced Vitamin C concentrations in the brain exceed those in blood by 10 fold. Dehydroascorbic acid readily enters the brain and is retained in the brain tissue in the form of ascorbic acid (ascorbic acid is not able to cross the blood-brain barrier). Therefore, transport of dehydroascorbic acid by the Glucose Transporter 1 (GLUT1, Glucose transporters are integral membrane glycoproteins involved in transporting glucose into most cells. GLUT1 is a major glucose transporter in the mammalian blood-brain barrier. It is present at high levels in primate erythrocytes and brain endothelial cells.) is a mechanism by which the brain acquires vitamin C. (OMIM 138140).
490-83-5
C00425
210328
17242
L-DEHYDRO-ASCORBATE
182283
[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO
C6H6O6
InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1
SBJKKFFYIZUCET-DUZGATOHSA-N
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
174.1082
174.016437924
0.04
2
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
0
-1
FDB021459
1-dehydroascorbate;1-dehydroascorbic acid;Dhaa;Dehydro-l-ascorbate;Dehydro-l-ascorbic acid;Dehydroascorbate;L-dehydroascorbate;L-dehydroascorbic acid;L-threo-2,3-hexodiulosonic acid gamma-lactone;L-threo-hexo-2,3-diulosono-1,4-lactone;Oxidized ascorbate;Oxidized ascorbic acid;Oxidized vitamin c
PW_C000977
DHAA
700
20
2022
14
12298
225
13404
222
77768
341
79118
115
121612
405
124170
376
127581
209
1783
Hydrogen peroxide
HMDB0003125
Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).
7722-84-1
C00027
784
16240
HYDROGEN-PEROXIDE
763
OO
H2O2
InChI=1S/H2O2/c1-2/h1-2H
MHAJPDPJQMAIIY-UHFFFAOYSA-N
peroxol
34.0147
34.005479308
2
hydrogen peroxide
0
0
FDB014562
Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;Hooh
PW_C001783
H2O2
98
9
113
5
188
8
551
14
627
28
755
15
1243
3
1691
2
1749
51
2534
22
3818
10
4749
13
4752
31
5495
126
5502
123
5510
127
5810
108
6005
147
7038
163
8396
151
11817
216
11886
215
12461
226
12709
291
12719
292
13028
301
13035
298
13040
302
13405
222
42658
315
77022
225
77047
294
77079
293
77500
113
77540
334
77598
115
77720
332
77725
337
77806
114
77810
111
77819
326
78073
329
78152
132
78598
112
120050
408
120102
122
120463
405
120595
409
120609
416
120954
407
121047
124
122120
382
122801
374
122814
443
122839
135
123097
376
123157
447
123165
448
123220
137
123234
452
123520
119
123611
118
124672
399
125428
482
125469
297
125709
478
125732
483
125748
488
125895
481
126103
299
126275
484
126967
502
126978
207
127006
205
127201
209
127215
208
127230
505
127356
206
127601
388
127838
389
31
Ascorbic acid
HMDB0000044
Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. [PubChem] Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants. (PMID: 10799361).
50-81-7
C00072
54670067
29073
ASCORBATE
10189562
DB00126
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
C6H8O6
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
176.1241
176.032087988
0.14
4
vitamin C
0
-1
FDB001224
(+)-sodium l-ascorbate;(+)-ascorbate;(+)-ascorbic acid;3-keto-l-gulofuranolactone;3-oxo-l-gulofuranolactone;Adenex;Allercorb;Antiscorbic vitamin;Antiscorbutic vitamin;Arco-cee;Ascoltin;Ascor-b.i.d.;Ascorb;Ascorbajen;Ascorbate;Ascorbic acid;Ascorbicab;Ascorbicap;Ascorbicin;Ascorbin;Ascorbutina;Ascorin;Ascorteal;Ascorvit;C-level;C-long;C-quin;C-span;C-vimin;Cantan;Cantaxin;Catavin c;Ce lent;Ce-mi-lin;Ce-vi-sol;Cebicure;Cebid;Cebion;Cebione;Cecon;Cee-caps td;Cee-vite;Cegiolan;Ceglion;Ceklin;Celaskon;Celin;Cell c;Cemagyl;Cemill;Cenetone;Cenolate;Cereon;Cergona;Cescorbat;Cetamid;Cetane;Cetane-caps tc;Cetane-caps td;Cetebe;Cetemican;Cevalin;Cevatine;Cevex;Cevi-bid;Cevimin;Cevital;Cevitamate;Cevitamic acid;Cevitamin;Cevitan;Cevitex;Cewin;Chewcee;Ciamin;Cipca;Citriscorb;Citrovit;Colascor;Concemin;Davitamon c;Dora-c-500;Duoscorb;Ferrous ascorbate;Hicee;Hybrin;Ido-c;Juvamine;Kangbingfeng;Kyselina askorbova;L(+)-ascorbate;L(+)-ascorbic acid;L-(+)-ascorbate;L-(+)-ascorbic acid;L-3-ketothreohexuronic acid lactone;L-ascorbate;L-ascorbic acid;L-lyxoascorbate;L-lyxoascorbic acid;L-threo-ascorbic acid;L-xyloascorbate;L-xyloascorbic acid;Laroscorbine;Lemascorb;Liqui-cee;Meri-c;Natrascorb;Natrascorb injectable;Planavit c;Proscorbin;Redoxon;Ribena;Ronotec 100;Rontex 100;Roscorbic;Rovimix c;Scorbacid;Scorbu c;Scorbu-c;Secorbate;Sodascorbate;Suncoat vc 40;Testascorbic;Vasc;Vicelat;Vicin;Vicomin c;Viforcit;Viscorin;Viscorin 100m;Vitace;Vitacee;Vitacimin;Vitacin;Vitamin c;Vitamisin;Vitascorbol;Xitix;Gamma-lactone l-threo-hex-2-enonate;Gamma-lactone l-threo-hex-2-enonic acid;Acide ascorbique;Acido ascorbico;Acidum ascorbicum;Acidum ascorbinicum;Ascorbinsaeure;E 300;E-300;E300
PW_C000031
VitC
679
31
698
20
1267
5
2021
14
6252
107
12146
151
12297
225
13402
222
42506
318
77752
129
77766
341
78429
334
79116
115
115855
336
120558
414
120993
408
121610
405
123192
450
123558
374
124168
376
125933
482
127392
502
127579
209
691
Xylulose 5-phosphate
HMDB0000868
Xylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of liver glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK; EC 2.7.1.11] in glycolysis and promotes the action of the transcription factor carbohydrate responsive element binding protein (ChREBP) to increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358).
60802-29-1
C00231
439190
16332
XYLULOSE-5-PHOSPHATE
388330
DB04034
OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O
C5H11O8P
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1
FNZLKVNUWIIPSJ-RFZPGFLSSA-N
{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
230.1098
230.01915384
-0.95
5
ribulose-5-phosphate
0
-2
FDB022290
D-xylulose 5-po4;D-xylulose 5-phosphate;D-xylulose-5-p;D-xylulose-5-phosphate;Xu-5-p;Xylulose 5-phosphate;Xylulose-p;Xylulose-phosphate;5-o-phosphono-d-threo-pentos-2-ulose;5-o-phosphono-d-xylulose;D-xylulose 5-phosphoric acid;D-xylulose-5-phosphoric acid
PW_C000691
Xyl-5-P
1776
2
13294
225
13298
151
77178
132
122188
124
124740
118
126348
299
127910
388
40862
L-ribulose 5-phosphate
OCC(=O)[C@@H](O)[C@@H](O)COP([O-])([O-])=O
L-ribulose 5-phosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. In Escherichia coli, RpiA catalyzes the interconversion of ribose-5-phosphate and ribulose-5-phosphate and is a key enzyme in the pentose phosphate pathway. (PMID 12182339) Interconversion of D-ribose-5-phosphate (R5P) and D-ribulose-5-phosphate is an important step in the pentose phosphate pathway. (PMID 18640127) A key player in LPS synthesis is the enzyme D-arabinose-5-phosphate isomerase (API), which catalyzes the reversible isomerization of D-ribulose-5-phosphate to D-arabinose-5-phosphate, a precursor of 3-deoxy-D-manno-octulosonate that is an essential residue of the LPS inner core. (PMID 20954237) Dihydroxybutanone phosphate synthase (DS) catalyzes a commitment step in riboflavin biosynthesis where ribulose 5-phosphate is converted to dihydroxybutanone phosphate and formate. (PMID 11053863) Ribose-5-phosphate isomerase A (RpiA) plays an important role in interconverting between ribose-5-phosphate (R5P) and ribulose-5-phosphate in the pentose phosphate pathway and the Calvin cycle. (PMID 19214439) (from ECMDB)
58226
OCC(=O)[C@@H](O)[C@@H](O)COP([O-])([O-])=O
C5H9O8P
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/p-2/t4-,5+/m0/s1
FNZLKVNUWIIPSJ-CRCLSJGQSA-L
(3S,4S)-1,3,4-trihydroxy-5-(phosphonatooxy)pentan-2-one
228.094
228.004601408
-0.63
3
L-ribulose 5-phosphate(2-)
-2
-2
PW_C040862
LR5P
40863
L-xylulose -5-phosphate
L-Xylulose 5-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). L-Xylulose 5-phosphate may be a unique E.coli metabolite. L-Xylulose -5-phosphate has the chemical formula C7H13O6P, and an average molecular weight of 224.15. L-Xylulose -5-phosphate is involved in a couple of pathways, which are Ascorbate Metabolism Pathway and L-Lyxose Degradation Pathway.
23615403
57829
CC(COP([O-])([O-])=O)C(C)C(=O)CO
C7H13O6P
InChI=1S/C7H15O6P/c1-5(4-13-14(10,11)12)6(2)7(9)3-8/h5-6,8H,3-4H2,1-2H3,(H2,10,11,12)/p-2
GOBYCGYLQSIFMQ-UHFFFAOYSA-L
1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
224.15
224.046072296
-0.83
1
1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one
-2
-2
L-xylulose-5-p, l-xylulose 5-phosphate dianion, 5-o-phosphonato-l-xylulose, 5-o-phosphonato-l-threo-pentos-2-ulose
PW_C040863
LX5P
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
7232
Probable L-ascorbate-6-phosphate lactonase ulaG
P39300
Involved in hydrolase activity. Probably catalyzes the hydrolysis of L-ascorbate-6-P into 3-keto-L-gulonate-6-P. Is essential for L-ascorbate utilization under anaerobic conditions. Also shows phosphodiesterase activity, hydrolyzing phosphodiester bond in the artificial chromogenic substrate bis-p-nitrophenyl phosphate (bis- pNPP).
ulaG
b4192
AP009048
3
3.1.1.-
8647
101
6581
L-xylulose/3-keto-L-gulonate kinase
P37677
Involved in phosphotransferase activity, alcohol group as acceptor. Catalyzes the phosphorylation of L-xylulose and 3-keto- L-gulonate. Is involved in L-lyxose utilization via xylulose, and may also be involved in the utilization of 2,3-diketo-L-gulonate.
lyx
b3580
AP009048
3
2.7.1.-; 2.7.1.53
6580
2,3-diketo-L-gulonate reductase
P37672
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor. Catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate.
dlgD
b3575
AP009048
3
1.1.1.130
8648
101
6603
L-ribulose-5-phosphate 4-epimerase ulaF
P39306
Involved in metal ion binding. Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. Is involved in the anaerobic L-ascorbate utilization.
ulaF
b4198
AP009048
3
5.1.3.4
7539
predicted L-xylulose 5-phosphate 3-epimerase
P37679
yiaR
b3582
3
5.1.3.22
6602
L-ribulose-5-phosphate 3-epimerase ulaE
P39305
Involved in intramolecular oxidoreductase activity, interconverting aldoses and ketoses. Catalyzes the isomerization of L-xylulose-5-phosphate to L-ribulose-5-phosphate. Is involved in the anaerobic L-ascorbate utilization.
ulaE
b4197
AP009048
3
5.1.3.22
6601
3-keto-L-gulonate-6-phosphate decarboxylase ulaD
P39304
Involved in magnesium ion binding. Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. Is involved in the anaerobic L-ascorbate utilization.
ulaD
b4196
AP009048
3
4.1.1.85
6582
3-keto-L-gulonate-6-phosphate decarboxylase sgbH
P37678
Involved in catalytic activity. Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. May be involved in the utilization of 2,3- diketo-L-gulonate.
sgbH
b3581
AP009048
3
4.1.1.85
6583
L-ribulose-5-phosphate 4-epimerase sgbE
P37680
Involved in metal ion binding. Catalyzes the isomerization of L-ribulose 5-phosphate to D-xylulose 5-phosphate. May be involved in the utilization of 2,3- diketo-L-gulonate.
sgbE
b3583
AP009048
3
5.1.3.4
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
6701
Ascorbate-specific phosphotransferase enzyme IIA component
P69820
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 ascorbate transport.
ulaC
b4195
AP009048
3
2.7.1.-
6253
109
6702
Ascorbate-specific phosphotransferase enzyme IIB component
P69822
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 ascorbate transport.
ulaB
b4194
AP009048
3
2.7.1.69
6254
109
7126
Ascorbate-specific permease IIC component ulaA
P39301
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system. The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport.
ulaA
b4193
AP009048
3
6255
109
1403
L-ascorbate 6-phosphate lactonase
3
PW_P001403
1635
7232
6
1404
L-xylulose kinase
3
PW_P001404
1636
6581
2
1405
2,3-diketo-L-gulonate reductase
3
PW_P001405
1637
6580
2
1410
L-ribulose 5-phosphate 4-epimerase
3
PW_P001410
1642
6603
1411
predicted L-xylulose 5-phosphate 3-epimerase
3
PW_P001411
1643
7539
1409
L-xylulose 5-phosphate 3-epimerase
3
PW_P001409
1641
6602
1412
3-keto-L-gulonate 6-phosphate decarboxylase UlaD
3
PW_P001412
1644
6601
1408
3-keto-L-gulonate 6-phosphate decarboxylase sgbH
3
PW_P001408
1640
6582
1413
L-ribulose-5-phosphate 4-epimerase
3
PW_P001413
1645
6583
1549
HPr - phosphorylated
3
PW_P001549
1828
7464
1550
HPr
3
PW_P001550
1829
7464
3619
L-ascorbate PTS permease
3
PW_P003619
10460
6701
10461
6702
10462
7126
2696
false
PW_R002696
Right
10593
40859
1
Compound
false
10594
1420
1
Compound
false
10595
40860
1
Compound
false
2689
1403
3.1.1.-
2697
false
PW_R002697
Right
10596
2724
1
Compound
false
10597
414
1
Compound
false
10598
40860
1
Compound
false
10599
1034
1
Compound
false
10600
40034
1
Compound
false
2690
1404
2.7.1.-
2698
false
PW_R002698
Right
10601
2783
1
Compound
false
10602
1144
1
Compound
false
10603
40034
1
Compound
false
10604
2724
1
Compound
false
10605
721
1
Compound
false
2691
1405
1.1.1.130
2700
true
PW_R002700
Right
10609
40861
1
Compound
false
10610
40034
1
Compound
false
10611
2783
1
Compound
false
2701
true
PW_R002701
Right
10612
977
1
Compound
false
10613
1420
1
Compound
false
10614
40861
1
Compound
false
2702
true
PW_R002702
Right
10615
1783
1
Compound
false
10616
40034
1
Compound
false
10617
31
2
Compound
false
10618
977
1
Compound
false
10619
31
1
Compound
false
10620
1420
2
Compound
false
2713
false
PW_R002713
Right
10651
40860
1
Compound
false
10652
40034
1
Compound
false
10653
40863
1
Compound
false
10654
1316
1
Compound
false
2702
1412
4.1.1.85
2709
false
PW_R002709
Right
10639
40860
1
Compound
false
10640
40034
1
Compound
false
10641
1316
1
Compound
false
10642
40863
1
Compound
false
2698
1408
2714
false
PW_R002714
Right
10655
40862
1
Compound
false
10656
691
1
Compound
false
2703
1413
5.1.3.4
2710
false
PW_R002710
Right
10643
40863
1
Compound
false
10644
40862
1
Compound
false
2699
1409
2707
false
PW_R002707
Right
10635
40862
1
Compound
false
10636
691
1
Compound
false
2696
1410
5.1.3.4
6126
false
PW_R006126
Right
25070
40863
1
Compound
false
25071
40862
1
Compound
false
6087
1411
6088
1409
136
PW_RCT000136
Right
804
136
31
Compound
1
107
805
136
1549
ProteinComplex
1
108
806
136
40859
Compound
1
108
807
136
1550
ProteinComplex
1
108
136
14548
40859
3
false
2550
1732
10
regular
100
110
14549
1420
49
false
2465
1633
10
regular
78
78
14550
40860
3
false
2549
1122
10
regular
100
120
14551
2724
3
false
2050
597
10
regular
100
110
14552
414
42
false
2205
577
10
regular
50
30
14553
1034
43
false
2526
712
10
regular
50
30
14554
40034
55
false
2521
519
10
regular
78
78
14555
2783
3
false
1403
597
10
regular
100
110
14556
1144
60
false
1553
702
10
regular
50
30
14557
40034
55
false
1563
523
10
regular
78
78
14558
721
59
false
1940
577
10
regular
50
30
14561
40861
3
false
1148
592
10
regular
100
120
14562
40034
55
false
1290
718
10
regular
78
78
14563
977
3
false
903
597
10
regular
100
110
14564
1420
49
false
1033
718
10
regular
78
78
14565
1783
56
false
636
708
10
regular
78
78
14566
40034
55
false
639
518
10
regular
78
78
14567
31
3
false
502
602
10
regular
100
100
14568
31
3
false
795
717
10
regular
100
100
14569
1420
49
false
805
518
10
regular
78
78
14584
691
3
false
850
947
10
regular
100
110
14586
40862
3
false
1300
1347
10
regular
100
110
14595
40034
55
false
2291
873
10
regular
78
78
14596
40863
3
false
1755
947
10
regular
100
110
14597
1316
52
false
1915
873
10
regular
78
78
14598
40034
55
false
2281
1253
10
regular
78
78
14599
1316
52
false
1911
1453
10
regular
78
78
14600
40863
3
false
1754
1347
10
regular
100
110
14601
691
3
false
850
1342
10
regular
100
110
19516
31
107
3
false
3050
1739
10
regular
100
100
2380807
40862
117
3
false
1305
946
10
regular
100
110
7497
7232
101
17
false
2509
1527
8
subunit
regular
180
85
7498
6581
6
false
2322
609
8
subunit
regular
160
80
7499
6580
101
6
false
1697
612
8
subunit
regular
160
80
7505
6603
2
false
1045
964
8
subunit
regular
150
70
7506
7539
2
false
1505
1367
8
subunit
regular
150
70
7508
6602
2
false
1499
967
8
subunit
regular
150
70
7512
6601
2
false
2054
967
8
subunit
regular
150
70
7513
6582
2
false
2054
1367
8
subunit
regular
150
70
7514
6583
2
false
1060
1364
8
subunit
regular
150
70
9363
7464
108
2
false
2725
1934
8
subunit
regular
150
70
9364
7464
108
2
false
2730
1592
8
subunit
regular
150
70
9365
6701
109
76
false
2845
1697
8
subunit
regular
150
70
9366
6702
109
76
false
2845
1812
8
subunit
regular
150
70
9367
7126
109
76
false
2845
1757
8
subunit
regular
150
70
6050
1403
541
7400
7497
6051
1404
541
7401
7498
6052
1405
541
7402
7499
6058
1410
541
7408
7505
6059
1411
541
7409
7506
6061
1409
541
7411
7508
6065
1412
541
7415
7512
6066
1408
541
7416
7513
6067
1413
541
7417
7514
7453
1549
541
108
9174
9363
7454
1550
541
108
9175
9364
7455
3619
541
109
9176
9365
9177
9366
9178
9367
22359
M2600 1732 C2599 1695 2599 1643 2599 1612
5
false
18
22360
M2543 1672 C2573 1672 2599 1675 2599 1612
5
false
18
22361
M2599 1242 C2599 1301 2599 1451 2599 1527
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22362
M2150 652 C2204 651 2259 650 2322 649
5
false
18
22363
M2230 607 C2232 647 2274 651 2322 649
5
false
18
22364
M2599 1122 C2600 985 2599 758 2599 649 C2523 649 2611 650 2482 649
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22365
M2551 712 C2552 679 2542 650 2482 649
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22366
M2560 597 C2559 623 2542 649 2482 649
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22367
M1503 652 C1557 651 1651 652 1697 652
5
false
18
22368
M1578 702 C1578 674 1623 652 1697 652
5
false
18
22369
M1602 601 C1601 650 1642 652 1697 652
5
false
18
22370
M2050 652 C1966 651 1942 651 1857 652
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22371
M1965 607 C1960 638 1911 650 1857 652
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22375
M1248 652 C1297 651 1286.5 651.5 1320.5 651.5
5
false
18
22376
M1329 718 C1317 696 1323 653 1360 652
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22377
M1403 652 C1371 652 1345.5 651.5 1318.5 651.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22378
M1003 652 C1046 652 1065 652.5 1114 652.5
5
false
18
22379
M1072 718 C1066 681 1084 652.5 1108 652.5
5
false
18
22380
M1148 652 C1119 652 1093 652.5 1057 652.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22381
M675 708 C676 681 700 651.5 749 651.5
5
false
18
22382
M678 596 C678 626 706 651.5 748 651.5
5
false
18
22383
M602 652 C653 652 700 651.5 751 651.5
5
false
18
22384
M903 652 C859 652 790 650.5 745 651.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22385
M845 717 C845 669 807 651.5 762 651.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22386
M844 596 C843 617 828 651.5 777 651.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22421
M2549 1182 C2548 1132 2549 1069 2548 1000 C2495 1000 2297 1003 2204 1002
5
false
18
22422
M2330 951 C2322 1009 2273 1003 2204 1002
5
false
18
22423
M1855 1002 C1910 1002 1981 1000 2054 1002
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22424
M1954 951 C1955 977 1989 1003 2054 1002
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22425
M2549 1182 C2549 1212 2549 1358 2550 1399 C2465 1399 2296 1400 2204 1402
5
false
18
22426
M2320 1331 C2320 1361 2303 1400 2204 1402
5
false
18
22427
M1950 1453 C1951 1404 1984 1403 2054 1402
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22428
M1854 1402 C1910 1403 1996 1401 2054 1402
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
22429
M1300 1402 C1233 1400 1273 1403 1210 1399
5
false
18
22430
M950 1397 C995 1399 1018 1399 1060 1399
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
29152
M3050 1789 C3021 1791 3034 1791 2995 1792
5
false
18
29153
M2650 1787 C2683 1787 2816 1793 2845 1792
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
29154
M2875 1969 C2916 1951 2923 1936 2920 1882
5
false
7
29155
M2880 1627 C2916 1639 2921 1661 2920 1697
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3231298
M1755 1002 C1703 1002 1711 1002 1649 1002
5
false
18
3231299
M1405 1001 C1458 1001 1473 1002 1499 1002
5
false
18
true
M 25.946855044164835 2354.261556296296 L 11 2353 L 17.380887721185843 2366.575134323078
false
3231376
M1305 1001 C1260 999 1236 999 1195 999
5
false
18
3231377
M950 1002 C1001 1000 990 1000 1045 999
5
false
18
true
M 294.94685504416486 2568.261556296296 L 280 2567 L 286.38088772118584 2580.575134323078
false
3231608
M1754 1402 C1723 1402 1704 1402 1655 1402
5
false
18
3231609
M1400 1402 C1445 1403 1470 1403 1505 1402
5
false
18
true
M 587.9468550441649 2299.261556296296 L 573 2298 L 579.3808877211858 2311.575134323078
false
3231916
M850 1002 C815 1002 801 1002 750 1002
5
false
18
3236673
M850 1397 C820 1397 780 1396 750 1396
5
false
18
3895
541
2696
13265
14548
22359
Left
13266
14549
22360
Left
13267
14550
22361
Right
4114
2689
6050
3896
541
2697
13268
14551
22362
Left
13269
14552
22363
Left
13270
14550
22364
Right
13271
14553
22365
Right
13272
14554
22366
Right
4115
2690
6051
3897
541
2698
13273
14555
22367
Left
13274
14556
22368
Left
13275
14557
22369
Left
13276
14551
22370
Right
13277
14558
22371
Right
4116
2691
6052
3899
541
2700
13281
14561
22375
Left
13282
14562
22376
Right
13283
14555
22377
Right
3900
541
2701
13284
14563
22378
Left
13285
14564
22379
Left
13286
14561
22380
Right
3901
541
2702
13287
14565
22381
Left
13288
14566
22382
Left
13289
14567
22383
Left
13290
14563
22384
Right
13291
14568
22385
Right
13292
14569
22386
Right
3913
541
2713
13327
14550
22421
Left
13328
14595
22422
Left
13329
14596
22423
Right
13330
14597
22424
Right
4129
2702
6065
3914
541
2709
13331
14550
22425
Left
13332
14598
22426
Left
13333
14599
22427
Right
13334
14600
22428
Right
4130
2698
6066
3915
541
2714
13335
14586
22429
Left
13336
14601
22430
Right
4131
2703
6067
715342
541
2710
117
2897080
14596
3231298
Left
2897081
2380807
3231299
Right
673130
2699
6061
715360
541
2707
117
2897152
2380807
3231376
Left
2897153
14584
3231377
Right
673148
2696
6058
715411
541
6126
2897361
14600
3231608
Left
2897362
14586
3231609
Right
673199
6087
6059
242
136
541
1385
19516
29152
Left
1386
14548
29153
Right
37
7453
29154
Left
38
7454
29155
Right
245
7455
170
92524
93024
541
14
false
600
967
16
regular
89627
14584
3231916
Left
92674
93024
541
14
false
600
1361
16
regular
89777
14601
3236673
Left
186268
720
1413
1.3
1.3
0
2
92
479
481
978
M425 525 C425 475 475 425 525 425 C1222 425 2128 425 2825 425 C2875 425 2925 475 2925 525 C2925 964 2925 1536 2925 1975 C2925 2025 2875 2075 2825 2075 C2128 2075 1222 2075 525 2075 C475 2075 425 2025 425 1975 C425 1536 425 964 425 525
1
true
6
2500.0
1650.0
979
M126 227 C126 177 176 127 226 127 C1105 127 2247 127 3126 127 C3176 127 3226 177 3226 227 C3226 848 3226 1654 3226 2275 C3226 2325 3176 2375 3126 2375 C2247 2375 1105 2375 226 2375 C176 2375 126 2325 126 2275 C126 1654 126 848 126 227
1
true
6
3100.0
2248.0
1300
15
ANAEROBIC
1410
1012
20
1.9
1.9
160
15
1301
15
AEROBIC
1415
1252
20
1.9
1.9
160
15