1848
Pathway
Methylglyoxal Degradation III
In E. coli there are several pathways for the removal of methylglyoxal. In this pathway, methylglyoxal is reduced to acetol by the action of various enzymes possessing methylglyoxal reductase activity. Most of the enzymes that have been characterized with this activity belong to the NADPH-dependent aldo-keto reductase subfamily of the aldo-keto reductase (AKR) superfamily. AKRs are found in both prokaryotes and eukaryotes and catalyze the reduction of carbonyl-containing aldehyde and/or ketone containing compounds to their corresponding alcohols. A few dual-specificity AKRs are also able to utilize NADH. An AKR from E. coli has been identified that is NADH-specific (AKR11B2, the product of gene ydjG). AKRs have been of considerable interest in metabolic engineering studies.
E. coli K-12 enzymes homologous to mammalian AKRs have been shown to catalyze the methylglyoxal reductase reaction. Overexpression of the aldo-keto reductase AKR14A1, encoded by the yghZ gene, leads to increased resistance to methylglyoxal. In addition, three other genes yeaE (yeaE), dkgA (yqhE), and dkgB (yafB) were shown to encode proteins with similar activities. All four proteins were purified, and shown to catalyze the reaction in vitro, in the presence of NADPH.
Prolonged incubation of E. coli cell-free extracts with methylglyoxal resulted in conversion of acetol to (S)-propane-1,2-diol. The enzyme proposed to catalyze (S)-propane-1,2-diol production is L-1,2-propanediol dehydrogenase / glycerol dehydrogenase. In bacteria (S)-propane-1,2-diol is a dead-end metabolite and exits the cell rapidly.
Although AKRs can reduce methylglyoxal to acetol, a methylglyoxal reductase (NADPH-dependent) encoded by an unknown gene was purified from E. coli and shown to convert methylglyoxal to lactaldehyde. (EcoCyc)
Metabolic
PW002079
Center
PathwayVisualizationContext2366
1626
1595
#000099
PathwayVisualization1832
1848
Methylglyoxal Degradation III
In E. coli there are several pathways for the removal of methylglyoxal. In this pathway, methylglyoxal is reduced to acetol by the action of various enzymes possessing methylglyoxal reductase activity. Most of the enzymes that have been characterized with this activity belong to the NADPH-dependent aldo-keto reductase subfamily of the aldo-keto reductase (AKR) superfamily. AKRs are found in both prokaryotes and eukaryotes and catalyze the reduction of carbonyl-containing aldehyde and/or ketone containing compounds to their corresponding alcohols. A few dual-specificity AKRs are also able to utilize NADH. An AKR from E. coli has been identified that is NADH-specific (AKR11B2, the product of gene ydjG). AKRs have been of considerable interest in metabolic engineering studies.
E. coli K-12 enzymes homologous to mammalian AKRs have been shown to catalyze the methylglyoxal reductase reaction. Overexpression of the aldo-keto reductase AKR14A1, encoded by the yghZ gene, leads to increased resistance to methylglyoxal. In addition, three other genes yeaE (yeaE), dkgA (yqhE), and dkgB (yafB) were shown to encode proteins with similar activities. All four proteins were purified, and shown to catalyze the reaction in vitro, in the presence of NADPH.
Prolonged incubation of E. coli cell-free extracts with methylglyoxal resulted in conversion of acetol to (S)-propane-1,2-diol. The enzyme proposed to catalyze (S)-propane-1,2-diol production is L-1,2-propanediol dehydrogenase / glycerol dehydrogenase. In bacteria (S)-propane-1,2-diol is a dead-end metabolite and exits the cell rapidly.
Although AKRs can reduce methylglyoxal to acetol, a methylglyoxal reductase (NADPH-dependent) encoded by an unknown gene was purified from E. coli and shown to convert methylglyoxal to lactaldehyde. (EcoCyc)
Metabolic
3
3890
12583903
Grant AW, Steel G, Waugh H, Ellis EM: A novel aldo-keto reductase from Escherichia coli can increase resistance to methylglyoxal toxicity. FEMS Microbiol Lett. 2003 Jan 21;218(1):93-9.
1848
Pathway
1
Cell
CL:0000000
4
Cardiomyocyte
CL:0000746
5
Hepatocyte
CL:0000182
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
2
Bacteria
2
Prokaryote
Bacteria
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
19
Schizosaccharomyces pombe
4896
Eukaryote
5
Cytoplasm
GO:0005737
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
1
Cytosol
GO:0005829
10
Cell Membrane
GO:0005886
19
sarcoplasmic reticulum
GO:0016529
35
Chloroplast
GO:0009507
3
Mitochondrial Matrix
GO:0005759
36
Membrane
GO:0016020
11
Extracellular Space
GO:0005615
12
Mitochondrial Inner Membrane
GO:0005743
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
25
Golgi apparatus
GO:0005794
1
Liver
BTO:0000759
72
9
5
cardiocyte
BTO:0001539
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
8
5
1
1
PW_BS000008
22
14
1
1
PW_BS000022
329
14
12
1
PW_BS000028
111
5
12
1
PW_BS000111
122
5
5
1
PW_BS000122
382
14
5
1
PW_BS000100
135
5
17
1
PW_BS000135
399
14
17
1
PW_BS000113
297
5
10
1
PW_BS000024
484
14
10
1
PW_BS000115
205
5
6
1
PW_BS000024
389
14
6
1
PW_BS000112
3
2
1
1
PW_BS000003
10
1
7
1
1
PW_BS000010
5
4
1
1
PW_BS000005
18
13
1
1
PW_BS000018
2
1
1
1
PW_BS000002
29
1
1
1
PW_BS000029
49
7
1
1
PW_BS000049
31
1
5
1
1
PW_BS000031
14
10
1
PW_BS000014
108
1
3
PW_BS000108
147
1
24
1
PW_BS000147
159
24
PW_BS000159
35
5
19
1
4
PW_BS000035
117
1
3
1
PW_BS000117
188
1
18
PW_BS000024
163
2
18
1
PW_BS000163
160
1
18
1
PW_BS000160
213
7
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
170
18
PW_BS000170
225
35
4
1
PW_BS000024
151
1
4
1
PW_BS000151
224
2
4
1
PW_BS000024
198
5
18
1
PW_BS000024
211
10
18
PW_BS000024
222
3
4
1
PW_BS000024
164
4
PW_BS000164
286
36
4
1
PW_BS000024
226
4
4
1
PW_BS000024
249
13
4
1
PW_BS000024
315
1
23
PW_BS000024
322
1
23
1
PW_BS000024
293
4
1
PW_BS000024
132
1
12
1
PW_BS000132
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
130
13
12
1
PW_BS000130
112
2
12
1
PW_BS000112
115
10
12
PW_BS000115
336
1
12
1
PW_BS000028
119
2
17
1
PW_BS000119
94
3
PW_BS000094
407
2
5
1
PW_BS000115
405
10
5
PW_BS000115
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
429
1
5
1
PW_BS000115
124
1
5
1
PW_BS000124
383
7
5
1
PW_BS000100
376
10
17
PW_BS000053
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
464
1
17
1
PW_BS000115
118
1
17
1
PW_BS000118
398
7
17
1
PW_BS000113
481
2
10
1
PW_BS000115
299
1
10
1
PW_BS000024
495
7
10
1
PW_BS000115
206
2
6
1
PW_BS000024
388
1
6
1
PW_BS000112
390
7
6
1
PW_BS000112
4
3
1
1
PW_BS000004
15
11
1
PW_BS000015
26
1
1
1
5
PW_BS000026
54
1
3
1
5
PW_BS000054
17
12
1
1
PW_BS000017
42
24
1
1
PW_BS000042
70
28
5
1
1
PW_BS000070
103
3
3
1
PW_BS000103
107
31
3
PW_BS000107
100
5
2
1
PW_BS000100
105
11
3
PW_BS000105
155
3
24
1
PW_BS000155
157
2
24
1
PW_BS000157
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
152
8
4
PW_BS000152
101
5
3
1
PW_BS000101
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
162
12
18
1
PW_BS000162
195
13
18
PW_BS000024
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
223
12
4
1
PW_BS000024
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
318
31
23
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
120
3
17
1
PW_BS000120
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
479
3
10
1
PW_BS000115
483
11
10
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
501
3
6
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
334
4
12
1
PW_BS000028
408
4
5
1
PW_BS000115
374
4
17
1
PW_BS000053
482
4
10
1
PW_BS000115
502
4
6
1
PW_BS000115
9
6
1
1
PW_BS000009
28
1
16
1
1
PW_BS000028
6
1
3
1
PW_BS000006
95
1
7
2
1
PW_BS000095
141
1
7
19
1
PW_BS000141
1
1
PW_BS000001
216
4
18
1
PW_BS000024
298
1
7
10
1
PW_BS000024
113
6
12
1
PW_BS000113
126
6
5
1
PW_BS000126
443
6
17
1
PW_BS000115
43
25
1
1
PW_BS000043
356
25
12
1
PW_BS000028
419
25
5
1
PW_BS000115
455
25
17
1
PW_BS000115
490
25
10
1
PW_BS000115
507
25
6
1
PW_BS000115
905
Pyruvaldehyde
HMDB0001167
Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.
78-98-8
C00546
880
17158
METHYL-GLYOXAL
857
DB03587
CC(=O)C=O
C3H4O2
InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
AIJULSRZWUXGPQ-UHFFFAOYSA-N
2-oxopropanal
72.0627
72.021129372
0.40
0
methylglyoxal
0
0
FDB008295
1,2-propanedione;1-ketopropionaldehyde;2-keto propionaldehyde;2-ketopropionaldehyde;2-oxo-propionaldehyde;2-oxopropanal;Acetylformaldehyde;Acetylformyl;Ketopropionaldehyde;Methylglyoxal;Propanedione;Propanolone;Pyroracemic aldehyde;Pyruvaldehyde;Pyruvic aldehyde;Alpha-ketopropionaldehyde;2-oxopropionaldehyde;Ch3cocho;A-ketopropionaldehyde;α-ketopropionaldehyde
PW_C000905
Pyruval
1177
8
2535
22
78074
329
78759
111
120875
122
122121
382
123451
135
124673
399
125851
297
126276
484
127525
205
127839
389
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
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
3018
Hydroxyacetone
HMDB0006961
Hydroxyacetone, also known as acetol or acetone alcohol, belongs to the class of organic compounds known as alpha-hydroxy ketones. These are organic compounds containing a carboxylic acid, and an amine group attached to the alpha carbon atom, relative to the C=O group. Hydroxyacetone exists as a liquid, soluble (in water), and a very weakly acidic compound (based on its pKa). Hydroxyacetone has been detected in multiple biofluids, such as feces and urine. Hydroxyacetone participates in a number of enzymatic reactions. In particular, hydroxyacetone can be biosynthesized from acetone. Hydroxyacetone can also be converted into hydroxyacetone phosphate. Outside of the human body, hydroxyacetone can be found in a number of food items such as bamboo shoots, pitanga, root vegetables, and arrowhead. This makes hydroxyacetone a potential biomarker for the consumption of these food products. Hydroxyacetone is an intermediate in glycine, serine and threonine metabolism (KEGG: C05235). It is generated from methylglyoxal via the oxidoreductases [EC 1.1.1.-].
116-09-6
C05235
8299
27957
21106125
CC(=O)CO
C3H6O2
InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3
XLSMFKSTNGKWQX-UHFFFAOYSA-N
1-hydroxypropan-2-one
74.0785
74.036779436
0.96
1
acetone alcohol
0
0
FDB012041
1-hydroxy-2-propanone;2-ketopropyl alcohol;Acetol;Acetone alcohol;Methylketol;Pyruvic alcohol;Pyruvinalcohol
PW_C003018
Acetol
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
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
40967
(S)-Propane-1,2-diol
CC(CO)O1,2-Propanediol (1,2-PDO) occurs in two stereoisomers - (S)-propane-1,2-diol and (R)-propane-1,2-diol. Both forms are produced by certain organisms. For example, during the catabolism of 6-deoxyhexoses [Suzuki68, Weimer84] or during the fermentation of glucose via methylglyoxal [TranDin85, Cameron86].
1,2-PDO is a bulk industrial chemical with a global demand of around 1.36 million tons/year [Shelley07]. It is widely used in the production of unsaturated polyester resin and as a nontoxic replacement of ethylene glycol in deicer and antifreeze products. Current commercial production of 1,2-PDO is mainly by a synthetic process that results in a racemic mixture.
29002
CC(O)CO
C3H8O2
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
DNIAPMSPPWPWGF-UHFFFAOYSA-N
propane-1,2-diol
76.0944
76.0524295
1.10
2
1,2-propanediol
0
0
(s)-propane-1,2-diol, (s)-1,2-propane-diol, (s)-1,2-propanediol, (s)-1,2-dihydroxypropane, l-1,2-propanediol
PW_C040967
Sp12di
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
7315
Uncharacterized protein yghZ
Q46851
Energy production and conversion. Specific function unknown.
yghZ
b3001
AP009048
3
1.1.1.-
6141
Glycerol dehydrogenase
P0A9S5
Involved in oxidoreductase activity. Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively.
gldA
b3945
AP009048
3
1.1.1.6
6816
2,5-diketo-D-gluconic acid reductase A
Q46857
Involved in oxidoreductase activity. Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives.
dkgA
b3012
AP009048
3
1.1.1.274
8870
101
6497
2,5-diketo-D-gluconic acid reductase B
P30863
Involved in oxidoreductase activity. Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG).
dkgB
b0207
AP009048
3
1.1.1.346
8871
101
4070
L-glyceraldehyde 3-phosphate reductase
25
PW_P004070
11080
7315
1
3935
L-1,2-propanediol dehydrogenase / glycerol dehydrogenase
3
PW_P003935
10914
6141
8
3949
methylglyoxal reductase
3
PW_P003949
10928
6816
10929
6497
6074
false
PW_R006074
Both
24853
905
1
Compound
false
24854
146
1
Compound
false
24855
40034
1
Compound
false
24856
3018
1
Compound
false
24857
143
1
Compound
false
6036
3949
1.1.1.274
6037
4070
1.1.1.-
6075
false
PW_R006075
Both
24858
3018
1
Compound
false
24859
1144
1
Compound
false
24860
40034
1
Compound
false
24861
40967
1
Compound
false
24862
721
1
Compound
false
6038
3935
1.1.1.6
10317
PW_T010317
10677
40967
1
Compound
117
107
Right
71354
905
3
false
537
426
10
regular
100
100
71355
146
62
false
642
581
10
regular
50
30
71356
40034
55
false
447
552
10
regular
78
78
71357
3018
3
false
534
906
10
regular
100
100
71358
143
61
false
654
826
10
regular
50
30
71359
1144
60
false
646
1046
10
regular
50
30
71360
40034
55
false
446
1002
10
regular
78
78
71361
40967
3
false
965
1096
10
regular
100
110
71362
721
59
false
740
1086
10
regular
50
30
2680183
40967
107
3
false
1290
1096
10
regular
100
110
32699
7315
2
false
511
671
8
subunit
regular
150
70
32700
6141
7
false
487
1113
8
subunit
regular
190
85
27483
4070
1832
32380
32699
27484
3935
1832
32381
32700
101307
M587 526 C587 556 586 641 586 671
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101308
M642 596 C595 600 586 641 586 671
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101309
M525 591 C587 592 586 641 586 671
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101310
M584 906 C584 876 586 771 586 741
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101311
M654 841 C592 841 586 771 586 741
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101312
M584 1006 C584 1036 582 1083 582 1113
5
false
18
true
M 294.7306351706878 532.7960839420218 L 279.7837801265229 531.5345276457258 L 286.16466784770876 545.1096619688042
false
101313
M646 1061 C591 1062 582 1083 582 1113
5
false
18
true
M 294.7306351706878 532.7960839420218 L 279.7837801265229 531.5345276457258 L 286.16466784770876 545.1096619688042
false
101314
M524 1041 C571 1042 582 1083 582 1113
5
false
18
true
M 294.7306351706878 532.7960839420218 L 279.7837801265229 531.5345276457258 L 286.16466784770876 545.1096619688042
false
101315
M965 1151 C931 1152 722 1149 677 1153
5
false
18
true
M 294.7306351706878 532.7960839420218 L 279.7837801265229 531.5345276457258 L 286.16466784770876 545.1096619688042
false
101316
M765 1116 C763 1148 740 1152 677 1153
5
false
18
true
M 294.7306351706878 532.7960839420218 L 279.7837801265229 531.5345276457258 L 286.16466784770876 545.1096619688042
false
3662369
M1065 1151 C1095 1151 1110 1151 1140 1151
83
false
18
3662370
M1290 1151 C1260 1151 1095 1151 1065 1151
83
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20704
1832
6074
80447
71354
101307
Left
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1832
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3662369
Left
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2680183
3662370
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702
479
1.0
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2
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481
3576
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