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Enzyme Nomenclature
Information on EC 1.1.1.1 - alcohol dehydrogenase
for references in articles please use BRENDA:EC1.1.1.1
Word Map on EC 1.1.1.1
- 1.1.1.1
- drosophila
- lactate
- melanogaster
- disulfiram
- catalase
- horse
-
retinoic
- hepatocytes
- injury
-
ingest
- methanol
- nicotinamide
- carcinoma
- dinucleotide
- pyrazole
-
ethanol-induced
- stomach
- intoxication
-
semialdehyde
- nadp+
- retinal
-
carcinogen
- cyp2e1
-
drinker
-
alcohol-induced
-
alcohol-related
-
asian
-
poison
-
abuse
-
nadp+-dependent
-
self-renewal
- benzaldehyde
-
flush
-
hydride
-
stem-like
- cyclophosphamide
- butanol
- etoh
-
first-pass
-
ethanol-treated
- diethyldithiocarbamate
-
allozymes
- acrolein
-
chaperone-like
- isopropanol
-
aversion
-
drank
- pargyline
- s-nitrosoglutathione
- ichthyosis
- synthesis
- medicine
- biotechnology
- degradation
- biofuel production
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The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
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EC NUMBER 
COMMENTARY 
1.1.1.1
-
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RECOMMENDED NAME
GeneOntology No.
alcohol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a secondary alcohol + NAD+ = a ketone + NADH + H+
-
-
-
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
ordered bi bi mechanism with cofactor adding first to form a binary enzyme complex
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
isoenzyme EE and SS: ordered bi bi mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
Theorell-Chance mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
kinetic mechanism is random for ethanol oxidation and compulsory ordered for acetaldehyde reduction
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
ordered bi-bi mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
rapid equilibrium random mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
rapid equilibrium random mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
Theorell-Chance mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
Theorell-Chance mechanism
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
oxidizes ethanol in an ordered bi-bi mechanism with NAD+ as the first substrate fixed
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
compulsory-order mechanism with the rate-limiting step being the dissociation of the product enzyme-NAD+ complex
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
mechanism is predominantly ordered with ethanol, but partially random with butanol
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
mechanism is predominantly ordered with ethanol, but partially random with butanol
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
Ser48 is involved in catalysis, isozyme gamma(2)gamma(2)
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
ordered bibi mechanism, structural and functional implications of amino acid residue 47
a primary alcohol + NAD+ = an aldehyde + NADH + H+
reaction mechanism, His51 is involved, but not essential, in catalysis facilitating the deprotonation of the hydroxyl group of water or alcohol ligated to the catalytic zinc
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
sequential reaction mechanism
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
ordered sequential bibi reaction mechanism, modeling of oxidation kinetic mechanism
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
detailed determination of the reaction and kinetic mechanisms, active site structure and determination of amino acid residues involved in catalysis, 3 isozymes
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
class IV alcohol dehydrogenase also functions as retinol dehydrogenase, reaction and kinetic mechanism: asymmetric rapid equilibrium random mechanism with 2 dead-end ternary complexes fro retinol oxidation and a rapid equilibrium ordered mechanism with one dead-end ternary complex for retinal reduction, a unique mechanistic form fro zinc-containing ADH in the medium chain dehydrogenase/reductase superfamily of enzymes
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
the catalytic triad consists of Cys44, His67, and Cys154, active site structure
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
catalytic mechanism involves a proton relay modulated by the coupled ionization of the active site Lys155/Tyr151 pair, and a NAD+ ribose 2'-OH switch, other active site residues are Ser138 and Trp144, ionization properties, substrate binding, overview
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
oxidizes ethanol in an ordered bi-bi mechanism with NAD+ as the first substrate fixed
-
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
the catalytic triad consists of Cys44, His67, and Cys154, active site structure
-
-
a primary alcohol + NAD+ = an aldehyde + NADH + H+
sequential reaction mechanism
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a primary alcohol + NAD+ = an aldehyde + NADH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
reduction
-
-
-
-
redox reaction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
alcohol:NAD+ oxidoreductase
A zinc protein. Acts on primary or secondary alcohols or hemi-acetals with very broad specificity; however the enzyme oxidizes methanol much more poorly than ethanol. The animal, but not the yeast, enzyme acts also on cyclic secondary alcohols.
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CAS REGISTRY NUMBER
COMMENTARY
9031-72-5
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cationic pyrazole-sensitive isoenzyme, anodic pyrazole-sensitive isoenzyme and cathionic pyrazole-in sensitive isoenzyme
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-
i.e. Pichia angusta, HpADH3 is not the major ADH in strain DL-1, gene ADH3
UniProt
i.e. Pichia angusta, HpADH3 is not the major ADH in strain DL-1, gene ADH3
UniProt
-
285581, 285582, 285584, 285585, 285586, 285587, 285588, 285589, 285591, 285592, 285594, 285595, 285609, 285610, 285641, 285647, 285648, 285653, 285657, 655206, 655233, 668487, 685703, 695889, 697215, 697660, 738096, 738394
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-
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285565, 285567, 285574, 654370, 669630, 686331, 687976, 689316, 691867, 697802, 722013, 722073, 738034
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class I isoenzymes: alpha,gamma2, gamma2gamma2, alpha,gamma1, alpha,beta1, beta1,gamma2, gamma1,gamma1, beta1,gamma1, beta1,beta1
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-
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285558, 285641, 285643, 285644, 285645, 285649, 654053, 655735, 655741, 667307, 668532, 669148, 685776, 687134, 687831, 688435, 688657, 688866, 689887, 695705, 696411, 697267, 697658, 735629, 735836, 736534, 737468, 738720, 738991, 739927
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UniProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
-
the enzyme belongs to the short-chain alcohol dehydrogenases
evolution
the class I type enzyme belongs to the medium-chain alcohol dehydrogenases, structural and evolutionary relationships of the pigeon enzyme, phylogenetic tree, overview
evolution
the class III type enzyme belongs to the medium-chain alcohol dehydrogenases, structural and evolutionary relationships of the dogfish enzyme, phylogenetic tree, overview
evolution
alcohol dehydrogenase is a fermentative enzyme that is highly conserved across species, from prokaryotes to fungi, plants, and animals
evolution
-
the enzyme belongs to the short-chain alcohol dehydrogenases
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evolution
-
alcohol dehydrogenase is a fermentative enzyme that is highly conserved across species, from prokaryotes to fungi, plants, and animals
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evolution
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the enzyme ADH3 belongs to the group III alcohol dehydrogenases
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metabolism
ADHE can be involved either in ethanol production or assimilation, or both, depending upon environmental conditions
physiological function
-
different fermentation product yields observed in different ethanol-producing thernophiles that employ the phosphoroclastic pathway for pyruvate metabolism are related to the specific activities and the direction of specific oxidoreductases that control electron flow. Thermoanaerobium brockii extracts contain reversible NAD- and NADP-linked alcohol dehydrogenase activities that are not effectively inhibited by low NAD(P) or ethanol
physiological function
Adh1 is the primary alcohol dehydrogenase responsible for the production of ethanol from the reduction of acetaldehyde in Kluyveromyces marxianus
physiological function
-
deletion of the bifunctional alcohol and aldehyde dehydrogenase gene adhE reduces ethanol production by more than 95%. In the deletion strains, fermentation products shift from ethanol to lactate production and result in lower cell density and longer time to reach maximal cell density. The deletion strain additionally contains a point mutation in the lactate dehydrogenase gene, which appears to deregulate its activation by fructose 1,6-bisphosphate, leading to constitutive activation of lactate dehydrogenase
physiological function
deletion of the bifunctional alcohol and aldehyde dehydrogenase gene adhE reduces ethanol production by more than 95%. In the deletion strain, fermentation products shift from ethanol to lactate production and result in lower cell density and longer time to reach maximal cell density. It loses more than 85% of alcohol dehydrogenase activity. Aldehyde dehydrogenase activity does not appear to be affected, although its activity is low in cell extracts. Adding ubiquinone-0 to the aldehyde dehydrogenase assay increases activity in the parent strain but does not increase activity in the adhE deletion strain
physiological function
-
in ethanol-tolerant mutant strain, EA, the tolerant phenotype is primarily due to a mutated bifunctional acetaldehyde-CoA/alcohol dehydrogenase gene (adhE), with a complete loss of NADH-dependent activity and concomitant acquisition of NADPH-dependent activity, which likely affects electron flow in the mutant strain. Mutant adhE allele alone confers increased ethanol tolerance
physiological function
deletion of the Aadh1 gene affects growth of the cells with 1-butanol, ethanol and glucose as the carbon source, and a strain which overexpresses the gene metabolizes 1-butanol more rapidly. Aadh1 is a major enzyme for the synthesis of ethanol and the degradation of 1-butanol in Blastobotrys adeninivorans
physiological function
-
Adh1 is the primary alcohol dehydrogenase responsible for the production of ethanol from the reduction of acetaldehyde in Kluyveromyces marxianus
-
physiological function
-
deletion of the bifunctional alcohol and aldehyde dehydrogenase gene adhE reduces ethanol production by more than 95%. In the deletion strains, fermentation products shift from ethanol to lactate production and result in lower cell density and longer time to reach maximal cell density. The deletion strain additionally contains a point mutation in the lactate dehydrogenase gene, which appears to deregulate its activation by fructose 1,6-bisphosphate, leading to constitutive activation of lactate dehydrogenase; in ethanol-tolerant mutant strain, EA, the tolerant phenotype is primarily due to a mutated bifunctional acetaldehyde-CoA/alcohol dehydrogenase gene (adhE), with a complete loss of NADH-dependent activity and concomitant acquisition of NADPH-dependent activity, which likely affects electron flow in the mutant strain. Mutant adhE allele alone confers increased ethanol tolerance
-
physiological function
-
deletion of the bifunctional alcohol and aldehyde dehydrogenase gene adhE reduces ethanol production by more than 95%. In the deletion strain, fermentation products shift from ethanol to lactate production and result in lower cell density and longer time to reach maximal cell density. It loses more than 85% of alcohol dehydrogenase activity. Aldehyde dehydrogenase activity does not appear to be affected, although its activity is low in cell extracts. Adding ubiquinone-0 to the aldehyde dehydrogenase assay increases activity in the parent strain but does not increase activity in the adhE deletion strain
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additional information
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ADH1 molecular modeling and molecular dynamics simulations, and comparison to rat ADH5 enzyme, overview
additional information
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ADH5 molecular modeling and molecular dynamics simulations, and comparison to human ADH1 enzyme, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(-)-carvone + NADH + H+
? + NAD+
1% activity compared to cyclohexanone
-
-
?
(1S,3S)-3-methylcyclohexanol + NAD+
(rac)-3-methylcyclohexanone + NADH + H+
125% activity compared to cyclohexanol
163% activity compared to cyclohexanone
-
r
(2E)-2-methylpent-2-enal + NADPH + H+
(2E)-2-methylpent-2-en-1-ol + NADP+
41.5% of the activity with (2E)-but-2-enal, yield 95% after 12 h
-
-
?
(2E)-3,7-dimethylocta-2,6-dienal + NADPH + H+
(2E)-3,7-dimethylocta-2,6-dien-1-ol + NADP+
37.4% of the activity with (2E)-but-2-enal, yield 87% after 12 h
-
-
?
(2E)-but-2-enal + NADPH + H+
(2E)-but-2-en-1-ol + NADP+
yield 96% after 12 h
-
-
r
(2E)-dec-2-enal + NADPH + H+
(2E)-dec-2-en-1-ol + NADP+
16.7% of the activity with (2E)-but-2-enal, yield 91% after 12 h
-
-
?
(2E)-hex-2-enal + NADPH + H+
(2E)-hex-2-en-1-ol + NADP+
41.7% of the activity with (2E)-but-2-enal, yield 98% after 12 h
-
-
?
(2E)-oct-2-enal + NADPH + H+
(2E)-oct-2-en-1-ol + NADP+
30.2% of the activity with (2E)-but-2-enal, yield 69% after 12 h
plus 27% oct-2-enyl ester
-
?
(6S)-5,6-dihydro-6-methyl-4H-thieno[2,3b]thiopyran-4-one-7,7-dioxide + NADH + H+
(4S,6S)-5,6-dihydro-4-hydroxy-6-methyl-4H-thieno[2,3b]thiopyran-7,7-dioxide + NAD+
-
-
-
-
-
(R)-1-indanol + NAD+
?
62% of activity compared to (S)-1-indanol
-
-
?
(R)-3-methylcyclohexanone + NADH + H+
? + NAD+
2% activity compared to cyclohexanone
-
-
?
(R)-alpha-tetralol + NAD+
?
58% of activity compared to (S)-1-indanol
-
-
?
(R)-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
-
-
r
(S)-1-phenyl-2-propanol + NAD+
phenylacetone + NADH + H+
-
9% activity compared to cyclohexanone
-
r
(S)-2-heptanol + NAD+
2-heptanone + NADH + H+
-
331% of the activity with 2-propanol
-
-
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
-
38% of the activity with 2-propanol
-
-
r
(S)-2-pentanol + NAD+
?
11% of activity compared to (S)-1-indanol
-
-
?
(S)-2-phenylpropanol + NAD+
(S)-2-phenylpropanal + NADH + H+
-
156% of the activity with 2-phenylethanol
-
-
?
(S)-4-phenylbutan-2-ol + NAD+
benzylacetone + NADH + H+
-
3% activity compared to cyclohexanone
-
r
(S)-alpha-tetralol + NAD+
?
12% of activity compared to (S)-1-indanol
-
-
?
(S)-perillylalcohol + NAD+
(S)-perillaldehyde + NADH + H+
52% activity compared to cyclohexanol
-
-
?
(Z)-hex-2-en-1-ol + NAD+
(Z)-hex-2-en-1-one + NADH
-
9.7% of the activity with ethanol
-
-
?
1,1-dichloroacetone + NADH + H+
1,1-dichloropropan-2-ol + NADH
-
1078% of the activity with phenyl trifluoromethyl ketone
-
-
?
1,2-hexanediol + NAD+
?
-
20% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1,2-pentanediol + NAD+
?
-
12% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1,3-butanediol + NAD+
?
-
39% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1-(3-bromophenyl)ethanol + NAD+
1-(3-bromophenyl)ethanone + NADH + H+
315% of the activity with 1-phenylethanol
-
-
?
1-(3-chlorophenyl)ethanol + NAD+
1-(3-chlorophenyl)ethanone + NADH + H+
205% of the activity with 1-phenylethanol
-
-
?
1-(4'-chlorophenyl)ethanol + NAD+
1-(4'-chlorophenyl)ethanone + NADH + H+
-
26% of the activity with (S)-(-)-1-phenylethanol
-
-
?
1-(4'-fluorophenyl)ethanol + NAD+
1-(4'-fluorophenyl)ethanone + NADH + H+
-
45% of the activity with (S)-1-phenylethanol
-
-
r
1-(4-bromophenyl)ethanol + NAD+
1-(4-bromophenyl)ethanone + NADH + H+
167% of the activity with 1-phenylethanol
-
-
?
1-(4-chlorophenyl)ethanol + NAD+
1-(4-chlorophenyl)ethanone + NADH + H+
151% of the activity with 1-phenylethanol
-
-
?
1-(4-methylphenyl)ethanol + NAD+
1-(4-methylphenyl)ethanone + NADH + H+
189% of the activity with 1-phenylethanol
-
-
?
1-(p-tolyl)-ethanol + NAD+
1-(4-methylphenyl)ethanone + NADH + H+
19% activity compared to cyclohexanol
26% activity compared to cyclohexanone
-
?
1-chloro-5-acetylfuro[2,3-c]pyridine + NADH + H+
1-chloro-5-(1-hydroxyethyl)furo[2,3-c]pyridine + NAD+
-
-
-
-
r
1-decalone + NADH + H+
decahydronaphthalen-1-ol + NAD+
85% of the activity compared to 1-phenyl-1,2-propanedione
-
-
?
1-heptanol + NAD+
heptanol + NADH + H+
-
56% of the activity with 2-propanol, in the reverse reaction 755% of the activity with phenyl trifluoromethyl ketone
-
-
r
1-hexanol + NAD+
?
-
15% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1-hydroxy-2-butanone + NADH + H+
butane-1,2-diol + NAD+
-
59% of the activity with N-benzyl-3-pyrrolidinone
-
-
?
1-hydroxymethyl-6-methylpyrene + NAD+
1-formyl-6-methylpyrene + NADH + H+
-
-
-
r
1-hydroxymethyl-8-methylpyrene + NAD+
1-formyl-8-methylpyrene + NADH + H+
-
-
-
r
1-octanol + 2 NADP+ + H2O
octanoic acid + 2 NADPH + 2 H+
-
-
-
r
1-octanol + NAD+
1-octanal + NADH + H+
-
6% of activity with N-benzyl-3-pyrrolidinol
-
-
?
1-pentanol + NAD+
pentanal + NADH + H*
-
8% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1-phenyl-1,2-ethanediol + NAD+
1-phenyl-2-propanone + NADH + H+
1% activity compared to cyclohexanol
-
-
r
1-phenyl-1,2-propandione + NADH + H+
1-phenyl-2-hydroxy-1-propanone + NAD+
-
146% of the activity with 2,2,2-trifluoroacetophenone
-
-
r
1-phenyl-1,2-propanedione + NADH
?
about 25% of the activity compared to isatin
-
-
?
1-phenyl-1-propanol + NAD+
1-phenyl-1-propanone + NADH + H+
-
59% of the activity with (S)-(-)-1-phenylethanol
-
-
?
1-phenyl-1-propanol + NAD+
1-phenylpropanal + NADH + H+
-
59% of the activity with (S)-1-phenylethanol
-
-
r
1-phenyl-1-propanol + NAD+
?
-
31% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
1-phenyl-2-propanone + NADH + H+
(S)-1-phenyl-2-propanol + NAD+
-
-
-
-
-
1-phenyl-3-butanone + NADH + H+
1-phenylbutan-3-ol + NAD+
-
353% of the activity with phenyl trifluoromethyl ketone
-
-
?
1-phenylethanol + NAD+
acetophenone + NADH + H+
-
1% activity compared to cyclohexanone
-
?
1-phenylethanol + NADP+
1-phenylethanone + NADPH + H+
-
-
-
?
12-hydroxylauric acid methyl ester + NAD+
12-oxo lauricacid methyl ester + NADH + H+
-
-
product is a key intermediate for biobased polyamide 12 production
-
?
12-oxolauric acid methyl ester + NADH + H+
12-hydroxylauric acid methyl ester + NAD+
-
-
-
-
?
2',3',4',5',6'-pentafluoroacetophenone + NADH + H+
1-(2,3,4,5,6-pentafluorophenyl)ethanol + NAD+
45% of the activity compared to 1-phenyl-1,2-propanedione
-
-
?
2,2'-dichlorobenzil + NADH + H+
1,2-bis(2-chlorophenyl)-2-hydroxyethanone + NAD+
-
-
-
?
2,2,2-trichloroethanol + NAD+
trichloroacetaldehyde + NADH + H+
-
-
-
-
?
2,2,2-trifluoro-1-phenylethanone + propan-2-ol
(1R)-2,2,2-trifluoro-1-phenylethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 99% enantiomeric excess
-
?
2,2,2-trifluoroacetophenone + NADH
2,2,2-trifluoro-1-phenylethanol + NAD+
about 35% of the activity compared to isatin
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(R)-2,2,2-trifluoro-1-phenylethanol + NADP+
180% of the activity with acetoin
-
-
r
2,2-difluoro-1-phenylethanone + propan-2-ol
(1R)-2,2-difluoro-1-phenylethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 94% enantiomeric excess
-
?
2,3'-dichloroacetophenone + NADH + H+
1-(2,3-dichlorophenyl)ethanol + NAD+
-
67% of the activity with phenyl trifluoromethyl ketone
-
-
?
2,3'-dichloroacetophenone + NADH + H+
2-chloro-1-(3-chlorophenyl)ethanol + NAD+
-
-
-
-
r
2,3-butanediol + NAD+
?
-
83% of the activity with (S)-N-benzyl-3-pyrrolidinol
-
-
?
2,3-butanedione + NADH + H+
?
-
activity is 1.6fold higher than with N-benzyl-3-pyrrolidinone
-
-
?
2,3-pentanedione + NADH
? + NADH
-
5.5% of the activity with acetaldehyde
-
-
?
2-(3-fluorobiphenyl-4-yl)propanal + NADH + H+
(S)-2-(3-(fluoro)biphenyl-4-yl)propanol + NAD+
2-(4-trifluoromethylphenyl)propanal + NADH + H+
(S)-2-(4-trifluoromethyl)phenylpropanol + NAD+
-
18 h, 55% yield, 98% enantiomeric excess
-
-
?
2-(6-methoxynaphthalen-2-yl)propanal + NADH + H+
(S)-2-(6-methoxynaphthalen-2-yl)propan-1-ol + NAD+
-
18 h, 96% yield, 98% enantiomeric excess
-
-
?
2-(naphthalen-1-yl)propanal + NADH + H+
(S)-2-(naphthalen-1-yl)propanol + NAD+
-
18 h, 90% yield, 80% enantiomeric excess
-
-
?
2-(naphthalen-2-yl)propanal + NADH + H+
(S)-2-(naphthalen-2-yl)propanol + NAD+
-
18 h, 57% yield, 94% enantiomeric excess
-
-
?
2-acetylpyrrole + NADH + H+
1-(1H-pyrrol-2-yl)ethanol + NAD+
-
70% of activity with N-benzyl-3-pyrrolidinone
-
-
?
2-butanone + NADH + H+
butan-2-ol + NAD+
-
2.8fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
2-butanone + NADPH + H+
butan-2-ol + NADP+
12.1% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
2-chloroacetophenone + NADH + H+
1-(2-chlorophenyl)ethanol + NAD+
-
low activity
-
-
r
2-chlorocyclohexanone + NADH + H+
? + NAD+
3% activity compared to cyclohexanone
-
-
?
2-decalone + NADH + H+
? + NAD+
28% activity compared to cyclohexanone
-
-
?
2-decanol + NAD+
2-decanone + NADH + H+
weak activity
-
-
r
2-ethylhexan-1-ol + NAD+
2-ethylhexanal + NADH
Sporotrichum pulverulentum
-
weak activity
-
-
?
2-fluoro-1-(4-chlorophenyl)ethanone + propan-2-ol
(1R)-2-fluoro-1-(4-chlorophenyl)ethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 98% enantiomeric excess
-
?
2-fluoro-1-(4-fluorophenyl)ethanone + propan-2-ol
(1R)-2-fluoro-1-(4-fluorophenyl)ethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 97% enantiomeric excess
-
?
2-fluoro-1-(4-iodophenyl)ethanone + propan-2-ol
(1R)-2-fluoro-1-(4-iodophenyl)ethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 99% enantiomeric excess
-
?
2-fluoro-1-phenylethanone + propan-2-ol
(1R)-2-fluoro-1-phenylethanol + acetone
in presence of propan-2-ol at 10% v/v, reduction of fluorinated ketones is catalyzed without addition of NADH
99% conversion, 99% enantiomeric excess
-
?
2-heptanol + NAD+
heptan-2-one + NADH + H+
62% of the activity with 1-phenylethanol
-
-
?
2-heptanone + NADH
(S)-2-heptanol + NAD+ + H+
-
-
79% enantiomeric excess
-
?
2-heptanone + NADH + H+
(R)-2-heptanol + NAD+
-
229% of the activity with phenyl trifluoromethyl ketone
99% enantiomeric excess
-
?
2-heptanone + NADPH + H+
heptan-2-ol + NADP+
6.8% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
2-hexanone + NADH + H+
?
-
activity is 1.6fold higher than with N-benzyl-3-pyrrolidinone
-
-
?
2-hexanone + NADH + H+
hexan-2-ol + NAD+
-
50.4fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
2-hexanone + NADPH + H+
hexan-2-ol + NADP+
5.9% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
2.4% of the activity with NADPH
-
-
?
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
-
-
-
?
2-methoxybenzaldehyde + NADH + H+
2-methoxybenzylalcohol + NAD+
-
13% of the activity with 2,2,2-trifluoroacetophenone
-
-
?
2-methoxybenzyl alcohol + NAD+
2-methoxybenzaldehyde + NADH + H+
-
25% of the activity with (S)-(-)-1-phenylethanol
-
-
?
2-methyl-2,4-pentanediol + NAD+
?
1% activity compared to cyclohexanol
-
-
?
2-methylbutyraldehyde + NADH + H+
2-methylbutanol + NAD+
-
1.4% of the activity with acetaldehyde
-
-
?
2-methylcyclohexanone + NADH + H+
2-methylcyclohexanol + NAD+
13% of the activity compared to 1-phenyl-1,2-propanedione
-
-
?
2-methylcyclohexanone + NADH + H+
? + NAD+
46% activity compared to cyclohexanone
-
-
?
2-methylpropionaldehyde + NADH + H+
2-methylpropanal + NAD+
-
3.3% of the activity with acetaldehyde
-
-
?
2-nitrobenzaldehyde + NADH + H+
(2-nitrophenyl)methanol + NAD+
-
33% of activity with N-benzyl-3-pyrrolidinone
-
-
?
2-nitrobenzaldehyde + NADH + H+
2-nitrobenzyl alcohol + NAD+
-
low activity
-
-
r
2-nonanol + NAD+
2-nonanone + NADH + H+
weak activity
-
-
r
2-octanone + NADPH + H+
octan-2-ol + NADP+
11.9% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
2-oxo-4-methylpentane + NADH
4-methylpentan-2-ol + NAD+
-
-
-
-
?
2-oxo-butyric acid + NADH + H+
2-hydroxybutyric acid + NAD+
-
15% of activity with N-benzyl-3-pyrrolidinone
-
-
?
2-oxopropanal + NADH + H+
? + NAD+
328% of the activity with acetoin
-
-
r
2-pentanone + NADH
(S)-2-pentanol + NAD+ + H+
-
-
60% enantiomeric excess
-
?
2-pentanone + NADPH + H+
pentan-2-ol + NADP+
11.9% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
2-phenylcyclohexanone + NADH + H+
? + NAD+
2% activity compared to cyclohexanone
-
-
?
2-phenylethanol + NAD+
2-phenylethanone + NADH + H+
57% activity compared to cyclohexanol
-
-
r
2-phenylpropanal + NADH + H+
(S)-2-phenylpropanol + NAD+
-
18 h, 74% yield, 98% enantiomeric excess
-
-
?
2-propanol + NAD+
aceton + NADH + H+
-
-
irreversible, no measurable activity with acetone
-
ir
2-[3-(2-phenyl-1,3-dioxolan-2-yl)phenyl]propanal + NADH + H+
(S)-2-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)propanol + NAD+
-
18 h, 95% yield, 61% enantiomeric excess
-
-
?
3',4'-dimethoxyphenylacetone + NADH + H+
1-(3,4-dimethoxyphenyl)propan-2-ol + NAD+
-
24% of the activity with phenyl trifluoromethyl ketone
-
-
?
3'-bromoacetophenone + NADH + H+
1-(3-bromophenyl)ethanol + NAD+
-
151% of the activity with phenyl trifluoromethyl ketone
-
-
?
3'-chloroacetophenone + NADH + H+
1-(3-chlorophenyl)ethanol + NAD+
-
70% of the activity with phenyl trifluoromethyl ketone
-
-
?
3'-methoxyacetophenone + NADH + H+
1-(3-methoxyphenyl)ethanol + NAD+
-
51% of the activity with phenyl trifluoromethyl ketone
-
-
?
3,3,5-trimethylcyclohexanone + NADH + H+
? + NAD+
2% activity compared to cyclohexanone
-
-
?
3,4-dimethylbenzyl alcohol + NAD+
3,4-dimethylbenzaldehyde + NADH + H+
45% activity compared to cyclohexanol
-
-
r
3,4-hexanedione + NADH + H+
?
-
77% of the activity with N-benzyl-3-pyrrolidinone
-
-
?
3,4-methylenedioxyphenyl acetone + NADH
(S)-(3,4-methylenedioxyphenyl)-2-propanol + NAD+ + H+
-
-
-
-
-
3,5-dimethylcyclohexanol + NAD+
3,5-dimethylcyclohexanone + NADH + H+
1% activity compared to cyclohexanol
-
-
r
3-acetylpyridine + NADH + H+
1-pyridin-3-ylethanol + NAD+
-
7.9fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
3-aminobenzyl alcohol + NAD+
3-aminobenzaldehyde + NADH + H+
8% activity compared to cyclohexanol
-
-
r
3-bromobenzyl alcohol + NAD+
3-bromobenzaldehyde + NADH + H+
-
-
-
-
?
3-bromobenzylalcohol + NAD+
3-bromobenzaldehyde + NADH + H+
-
-
-
-
?
3-chloro-2-butanone + NADH + H+
3-chlorobutan-2-ol + NAD+
-
151% of the activity with phenyl trifluoromethyl ketone
-
-
?
3-heptanol + NAD+
3-heptanone + NADH + H+
-
93% of the activity with 2-propanol
-
-
r
3-methoxy-1-phenylpropan-1-one + NADH
3-methoxy-1-phenylpropan-1-ol + NAD+
-
-
-
-
?
3-methoxybenzaldehyde + NADH + H+
3-methoxybenzyl alcohol + NAD+
-
-
-
-
r
3-methoxybenzaldehyde + NADH + H+
3-methoxybenzylalcohol + NAD+
-
14% of the activity with 2,2,2-trifluoroacetophenone
-
-
?
3-methoxybenzylalcohol + NAD+
3-methoxybenzaldehyde + NADH + H+
-
-
-
-
?
3-methyl-2-cyclohexenone + NADH + H+
? + NAD+
1% activity compared to cyclohexanone
-
-
?
3-methylbutan-2-ol + NAD+
3-methylbutan-2-one + NADH
-
R-(-)-3-methylbutan-2-ol and S-(+)-3-methylbutan-2-ol
-
-
?
3-methylbutanol + NAD+
3-methylbutanone + NADH + H+
133% activity compared to cyclohexanol
-
-
r
3-methylbutyraldehyde + NADH + H+
3-methylbutanol + NAD+
-
2.9% of the activity with acetaldehyde
-
-
?
3-methylcyclohexanol + NAD+
3-methylcyclohexanone + NADH + H+
14% of activity compared to (S)-1-indanol
-
-
?
3-methylcyclohexanol + NAD+
?
10% of the activity compared to isoborneol
-
-
?
3-methylcyclohexanone + NADH + H+
3-methylcyclohexanol + NAD+
33% of the activity compared to 1-phenyl-1,2-propanedione
-
-
?
3-methylphenylethyl alcohol + NAD+
?
64% activity compared to cyclohexanol
-
-
?
3-pentanone + NADPH + H+
pentan-3-ol + NADP+
7.1% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
3-penten-2-one + NADH + H+
? + NAD+
2% activity compared to cyclohexanone
-
-
?
3-phenylpropanol + NAD+
3-phenylpropanal + NADH + H+
-
135% of the activity with 2-phenylethanol
-
-
?
3-phenylpropionaldehyde + NADH
3-phenylpropan-1-ol + NAD+
-
1218% of the activity with phenyl trifluoromethyl ketone
-
-
?
3-phenylpropionaldehyde + NADH + H+
3-phenylpropanol + NAD+
-
6.9fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
3beta,17beta-dihydroxy-5beta-androstane + NAD+
5beta-androstan-3,17dione + NADH
-
-
-
-
?
3beta,7alpha,12alpha-trihydroxy-5beta-cholanoic acid + NAD+
? + NADH
-
-
-
-
?
3beta-hxdroxy-5alpha-cholanoate + NAD+
3-oxo-5alpha-cholanoate + NADH
-
-
-
-
?
4'-bromoacetophenone + NADH + H+
1-(4-bromophenyl)ethanol + NAD+
-
77% of the activity with phenyl trifluoromethyl ketone
-
-
?
4'-chloroacetophenone + NADH + H+
1-(4-chlorophenyl)ethanol + NAD+
-
60% of the activity with phenyl trifluoromethyl ketone
-
-
?
4'-chlorobutyrophenone + NADH + H+
1-(4-chlorophenyl)butan-1-ol + NAD+
-
10% of the activity with 2,2,2-trifluoroacetophenone
-
-
?
4-acetylpyridine + NADH + H+
1-pyridin-4-ylethanol + NAD+
-
64.5fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
4-bromobenzyl alcohol + NAD+
4-bromobenzaldehyde + NADH + H+
-
-
-
-
?
4-bromobenzylalcohol + NAD+
4-bromobenzaldehyde + NADH + H+
-
-
-
-
?
4-carboxybenzaldehyde + NADH + H+
4-carboxybenzyl alcohol + NAD+
-
-
-
-
?
4-carboxybenzaldehyde + NADH + H+
4-carboxybenzylalcohol + NAD+
-
-
-
-
?
4-ethylcyclohexanol + NAD+
4-ethylcyclohexanone + NADH + H+
60% activity compared to cyclohexanol
-
-
r
4-ethylcyclohexanone + NADH + H+
? + NAD+
22% activity compared to cyclohexanone
-
-
?
4-hydroxy-2-butanone + NADH + H+
2,4-dihydroxybutane + NAD+
-
26% of the activity with phenyl trifluoromethyl ketone
-
-
?
4-hydroxynonenal + NADH + H+
4-hydroxynonenol + NAD+
-
substrate of isozyme ADH4
-
-
r
4-methoxy-1-naphthaldehyde + NAD+
4-methoxy-1-naphthol + NADH + H+
-
fluorogenic substrate of class I and II isozymes
-
-
?
4-methoxy-1-naphthaldehyde + NAD+
4-methoxy-1-naphthyl alcohol + NADH + H+
-
substrate for class I ADH
-
-
?
4-methoxy-1-naphthaldehyde + NADH + H+
4-methoxynaphthalene-1-carbaldehyde + NAD+
-
substrate for class I ADH
-
-
r
4-methoxybenzaldehyde + NADH + H+
4-methoxybenzyl alcohol + NAD+
-
-
51% of the activity with butan-2-ol
-
?
4-methoxybenzaldehyde + NADH + H+
4-methoxybenzylalcohol + NAD+
-
13% of the activity with 2,2,2-trifluoroacetophenone
-
-
?
4-methoxybenzylalcohol + NAD+
4-methoxybenzaldehyde + NADH + H+
-
-
-
-
r
4-methoxyphenylacetone + NADH
(2S)-1-(4-methoxyphenyl)propan-2-ol + NAD+ + H+
-
-
-
-
?
4-methylcyclohexanol + NAD+
4-methylcyclohexanone + NADH + H+
56% activity compared to cyclohexanol
-
-
r
4-methylcyclohexanone + NADH + H+
4-methylcyclohexanol + NAD+
60% of the activity compared to 1-phenyl-1,2-propanedione
-
-
?
4-methylcyclohexanone + NADH + H+
? + NAD+
25% activity compared to cyclohexanone
-
-
?
4-nitrobenzaldehyde + NADH + H+
4-nitrobenzylalcohol + NAD+
-
-
-
-
?
4-nitrobenzyl alcohol + NAD+
4-nitrobenzaldehyde + NADH + H+
94% activity compared to benzyl alcohol
-
-
?
4-nitrosodimethylaniline + NAD+
? + NADH + H+
-
photometric assay substrate
-
-
?
4-phenylbutan-2-one + NADH
4-phenylbutan-2-ol + NAD+
-
-
-
-
?
5-acetyl-7-chlorofuro[2,3-c]pyridine + NADH + H+
5-(1-hydroxyethyl)-7-chlorofuro[2,3-c]pyridine + NAD+
-
-
-
-
r
5-acetylfuro[2,3-c]pyridine + NADH + H+
5-(1-hydroxyethyl)furo[2,3-c]pyridine + NAD+
-
-
-
-
r
5alpha-androstan-17beta-ol-3-one + NADH + H+
3beta,17beta-dihydroxy-5alpha-androstan + NAD+
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH
-
low activity
-
-
?
5beta-cholanic acid-3-one + NADH
5beta-cholanic acid-3-ol + NAD+
-
low activity
-
-
?
5beta-pregnan-21-ol-3,20-dione hemisuccinate + NADH
5beta-pregnan-3,20,21-trione hemisuccinate + NADH
-
-
-
-
?
6-benzyloxy-3,5-dioxo-hexanoic acid ethyl ester + NADH + H+
(3R,5S)-6-benzyloxy-3,5-dihydroxy-hexanoic acid ethyl ester + NAD+
-
-
-
-
-
6-methoxy-2-naphthaldehyde + NADH + H+
(6-methoxynaphthalen-2-yl)methanol + NAD+
-
substrate for class II ADH
-
-
r
6-methoxy-2-naphthaldehyde + NADH + H+
6-methoxy-2-naphthyl alcohol + NAD+
-
substrate for class II ADH
-
-
?
6-methoxy-2-naphthaldehyde + NADH + H+
6-methoxy-2-naphtol + NAD+
-
class II isozyme, reductive activity
-
-
?
a primary alcohol + NAD+
an aldehyde + NADH + H+
-
ADH3 is involved in multiple cellular pathways, as diverse as formaldehyde detoxification, retinoid metabolism and NO homeostasis, ADH3 is considered to play only a minor role in hepatic alcohol metabolism because ethanol concentrations rarely exceed 50 mM
-
-
?
acetoin + NAD+
diacetyl + NADH
18% of the activity with 2,3-butanediol
-
-
?
acetone + NAD+ + H2O
? + NADH + H+
about 5% of the activity with 1-octanol
-
-
r
acetone + NADH + H+
propan-2-ol + NAD+
-
1.9fold higher activity compared to activity with N-benzyl-3-pyrrolidinone
-
-
?
acetone + NADPH + H+
propan-2-ol + NADP+
14.7% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
acetophenone + NADH
(R)-alpha-phenyl ethanol + NAD+
-
the enzyme exhibits high stereoselectivity in the desymmetrization of the prochiral ketone acetophenone, producing optically pure (R)-alpha-phenyl ethanol at high conversion
-
-
?
acetophenone + NADH + H+
(R)-1-phenylethanol + NAD+
-
6% of the activity with phenyl trifluoromethyl ketone, in the reverse reaction 87% of the activity with 2-propanol
99% enantiomeric excess
-
?
acetophenone + NADH + H+
(S)-(-)-1-phenylethanol + NAD+
-
more than 99% enantiomeric excess
-
-
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
-
99% enantiomeric excess
-
r
acetophenone + NADPH + H+
1-phenylethanol + NADP+
5.1% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
acetylacetone + NADH + H+
?
-
63% of the activity with N-benzyl-3-pyrrolidinone
-
-
?
acetylacetone + NADH + H+
acetophenone + NADH + H+
1% activity compared to cyclohexanone
1% activity compared to cyclohexanone
-
r
all-trans retinal + NADH + H+
all-trans retinol + NAD+
26.8% of the activity with butan-1-ol
-
-
?
alpha-ethyl benzoylformate + NADH + H+
ethyl (R)-(-)-mandelate + NAD+
-
-
95% enantiomeric excess
-
r
alpha-methyl benzoylformate + NADH + H+
methyl (R)-mandelate + NAD+
-
-
92% enantiomeric excess
-
r
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
107% of the activity with (2E)-but-2-enal, yield 99% after 12 h
-
-
r
benzil + NADH + H+
(R)-benzoin + NAD+
62% of the activity compared to 1-phenyl-1,2-propanedione. The enzyme catalyses the asymmetric reduction of benzil to (R)-benzoin with both excellent conversion (98%) and optical purity (98%) by way of an efficient in situ NADH-recycling system involving a second thermophilic ADH
-
-
?
benzoin + NADH + H+
1,2-diphenylethane-1,2-diol
-
13% of activity with N-benzyl-3-pyrrolidinone
-
-
?
benzoylformic acid + NADPH + H+
mandelate + NADP+
2.4% of the activity with 2-hydroxyacetophenone and NADPH
-
-
?
benzyl alcohol + NAD+
benzaldehyde + acycloNADH + H+
-
acycloNAD+ i.e. NAD+-analogue, where the nicotinamide ribosyl moiety has been replaced by the nicotinamide (2-hydroxyethoxy)methyl moiety
-
-
?
benzyloxycarbonyl-3-pyrrolidinone + NADH + H+
(S)-benzyloxycarbonyl-3-pyrrolidinol + NAD+
-
production with 99.6% enantiomeric excess
-
-
?
butan-1-ol + NAD+
butanal + acycloNADH + H+
-
acycloNAD+ i.e. NAD+-analogue, where the nicotinamide ribosyl moiety has been replaced by the nicotinamide (2-hydroxyethoxy)methyl moiety
-
-
?
butan-2-ol + NAD+
butanone + NADH + H+
-
-
83% of the activity with butan-2-ol
-
?
butanal + NADH
1-butanol + NAD+ + H+
-
% of the activity with phenyl trifluoromethyl ketone
-
-
ir
butyraldehyde + NADH + H+
butanol + NAD+
-
56% of the activity with acetaldehyde
-
-
?
butyraldehyde + NADPH + H+
butanol + NADP+
-
22% of the activity with NADH
-
-
?
choline + NAD+
? + NADH + H+
3% activity compared to benzyl alcohol
-
-
?
cis-4-methylcyclohexanol + NAD+
4-methylcyclohexanone + NADH
-
-
-
-
?
cis-decahydro-1-naphthol + NAD+
?
11% of activity compared to (S)-1-indanol
-
-
?
cyclohexanone + NADH + H+
?
-
activity is 2.1fold higher than with N-benzyl-3-pyrrolidinone
-
-
?