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Information on EC 1.1.1.B3 - (S)-specific secondary alcohol dehydrogenase
for references in articles please use BRENDA:EC1.1.1.B3
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preliminary BRENDA-supplied EC number
EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.B3 (S)-specific secondary alcohol dehydrogenase
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
showSynonyms
short chain dehydrogenase, acetophenone reductase, nad+-dependent adh, (s)-specific secondary alcohol dehydrogenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-1-phenylethanol dehydrogenase
acetophenone reductase
ADH1
ADHTt
APRD
carbonyl reductase (NADH, specific for (S)-configuration of alcohol)
-
NAD+-dependent ADH
PED
short-chain NAD(H)-dependent alcohol dehydrogenase
SOU1
TtADH
additional information
short-chain NAD(H)-dependent alcohol dehydrogenase
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
-
-
additional information
-
the enzyme belongs to the short-chain dehydrogenase/reductase, SDR, superfamily
additional information
-
the enzyme belongs to the short-chain dehydrogenases/reductase superfamily
additional information
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
the enzyme belongs to the short-chain dehydrogenase/reductase, SDR, superfamily
-
additional information
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
the enzyme belongs to the short-chain dehydrogenases/reductase superfamily
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-R-CHOH-R' + NAD+ = R-CO-R' + NADH + H+
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
sec-alcohol:NAD(P)+ oxidoreductase (specific for (S)-configuration of alcohol)
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-2-butanol + NAD+
2-butanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 6% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 30% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-2-pentanol + NAD+
2-pentanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 15% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 0.5% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 5.6% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-3-phenyl-1-indanol + NADH + H+
(R)-3-phenyl-1-indanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
(S)-1,3-butanediol + NAD+ + H+
4-hydroxy-2-butanone + NADH
-
Substrates: -
Products: enantioselective oxidation of the (S)-isomer
Products: enantioselective oxidation of the (S)-isomer
?
(S)-1-phenyl 2-propanol + NADP+
phenylacetone + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
(S)-1-phenylethanol + NAD+
1 phenylethanone + NADH + H+
-
Substrates: 99% ethanoselective reaction
Products: -
Products: -
r
(S)-1-[4-(1-hydroxyethyl)phenyl]-methylketone + NADH + H+
(S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
(S)-3-butyn-2-ol + NAD+
but-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 6.9% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-3-pentyn-2-ol + NAD+
pent-3-yn-2-one + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 33% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-3-phenyl-1-indanone + NADH + H+
(S)-3-phenyl-1-indanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
(S)-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
Substrates: 99% ethanoselective reaction
Products: -
Products: -
r
1-(3-fluorophenyl)ethan-1-ol + NADP+
1-(3-fluorophenyl)ethan-1-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(3-methoxyphenyl)propan-2-ol + NADP+
1-(3-methoxyphenyl)propan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(3-methylphenyl)ethan-1-ol + NADP+
1-(3-methylphenyl)ethan-1-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(4-fluorophenyl)ethan-1-ol + NADP+
1-(4-fluorophenyl)ethan-1-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(4-fluorophenyl)propan-2-ol + NADP+
1-(4-fluorophenyl)propan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(4-methylphenyl)ethan-1-ol + NADP+
1-(4-methylphenyl)ethan-1-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(4-methylphenyl)propan-2-ol + NADP+
1-(4-methylphenyl)propan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-(furan-2-yl)methylketone + NADH + H+
(S)-1-(furan-2-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
1-chloroacetophenone + NADH + H+
(1S)-2-chloro-1-phenylethanol + NAD+
-
Substrates: -
Products: more thasn 99% enantiomeric excess
Products: more thasn 99% enantiomeric excess
?
1-hexanal + NADH + H+
hexan-1-ol + NAD+
Nocardia fusca AKU 2123
-
Substrates: 254% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
1-phenoxypropan-2-ol + NADP+
1-phenoxypropan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-phenylbutan-2-ol + NADP+
1-phenylbutan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-phenylpentan-1-one + NADH + H+
1-phenylpentan-1-ol + NAD+
Substrates: -
Products: -
Products: -
?
1-phenylpropan-1-one + NADH + H+
1-phenylpropan-1-ol + NAD+
Substrates: -
Products: -
Products: -
?
1-phenylpropan-2-ol + NADP+
1-phenylpropan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
1-tetralone + NADH + H+
(S)-1,2,3,4-tetrahydronaphthalen-1-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2'-fluoroacetophenone + NADH + H+
(S)-1-(2-fluorophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2'-hydroxyacetophenone + NADH + H+
(S)-2-(1-hydroxyethyl)phenol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2,2,2-trifluoroacetophenone + NADH + H+
(S)-1-phenyl-2,2,2-trifluoroethan-1-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2,2,2-trifluoroacetophenone + NADH + H+
?
-
Substrates: completely enantioselective reaction
Products: -
Products: -
r
2,2-dichloroacetophenone + NADH + H+
(S)-2,2-dichloro-1-phenylethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2,2-difluoroacetophenone + NADH + H+
(S)-2,2-difluoro-1-phenylethan-1-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2,3-butanedione + NADH + H+
? + NAD+
Substrates: 9% of the activity with ethyl 4-chloro-3-oxobutanoate
Products: -
Products: -
?
2,3-butanedione + NADPH + H+
? + NADP+
Substrates: -
Products: -
Products: -
?
2,3-pentanedione + NADH + H+
? + NAD+
Substrates: 82% of the activity with ethyl 4-chloro-3-oxobutanoate
Products: -
Products: -
?
2,4'-dichloroacetophenone + NADH + H+
(S)-2-chloro-1-(4-chloro-phenyl)-ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2-acetylpyridine + NADH + H+
(S)-1-(pyridin-2-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2-acetylthiophene + NADH + H+
(S)-1-(thiophen-2-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2-chloroacetophenone + NADH + H+
(R)-2-chloro-1-phenylethanol + NAD+
-
Substrates: 100% (R)-enantiospecific product
Products: -
Products: -
r
2-cyanoacetophenone + NADH + H+
(S)-3-hydroxy-3-phenylpropanenitrile + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2-decanone + NADH + H+
(S)-2-decanol + NAD+
Nocardia fusca AKU 2123
-
Substrates: 159% of the activity with (RS)-2-hexanol
Products: reaction is stereoselective
Products: reaction is stereoselective
r
2-fluoroacetophenone + NADH + H+
(S)-2-fluoro-1-phenylethan-1-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
2-heptanone + NADH + H+
(S)-2-heptanol + NAD+
Nocardia fusca AKU 2123
-
Substrates: 334% of the activity with (RS)-2-hexanol
Products: reaction is stereoselective
Products: reaction is stereoselective
r
2-hexanone + NADH + H+
(S)-2-hexanol + NAD+
Nocardia fusca AKU 2123
-
Substrates: 225% of the activity with (RS)-2-hexanol
Products: reaction is stereoselective
Products: reaction is stereoselective
r
2-octanone + NADH + H+
(S)-2-octanol + NAD+
Nocardia fusca AKU 2123
-
Substrates: 223% of the activity with (RS)-2-hexanol
Products: reaction is stereoselective
Products: reaction is stereoselective
r
3'-aminoacetophenone + NADH + H+
(S)-1-(3-aminophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-bromoacetophenone + NADH + H+
(S)-1-(3-bromophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-chloroacetophenone + NADH + H+
(S)-1-(3-chlorophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-fluoroacetophenone + NADH + H+
(S)-1-(3-fluorophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-hydroxyacetophenone + NADH + H+
(S)-3-[(1)-1-hydroxyethyl]phenol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-methoxyacetophenone + NADH + H+
(S)-1-(3-methoxyphenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3'-methylacetophenone + NADH + H+
(S)-1-(3-methylphenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-(3-bromo-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-bromophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-(3-chloro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-chlorophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-(3-fluoro-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-(3-fluorophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-(3-methoxyphenyl)-3-oxo-propionic acid methylester + NADH + H+
(S)-methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester + NADH + H+
(S)-methyl 3-hydroxy-3-(4-methoxyphenyl)propanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-acetylpyridine + NADH + H+
(S)-1-(pyridin-3-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-coumaranone + NADH + H+
(S)-2,3-dihydro-1-benzofuran-3-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
3-heptanone + NADH + H+
3-hexanol + NADH + H+
Substrates: -
Products: -
Products: -
?
4'-acetyl acetophenone + NADH + H+
(S)-1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-acetylbiphenyl + NADH + H+
(S)-1-(biphenyl-4-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-acetylphenyl methanesulfonate + NADH + H+
(S)-4-(1-hydroxyethyl)phenyl methanesulfonate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-aminoacetophenone + NADH + H+
(S)-1-(4-aminophenyl)ethanol + NAD+
-
Substrates: 50% (S)-enantiospecific product
Products: -
Products: -
r
4'-bromoacetophenone + NADH + H+
(S)-1-(4-bromophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-chloroacetophenone + NADH + H+
(1S)-1-(4-chlorophenyl)ethanol + NAD+
-
Substrates: 83% of the activity with acetophenone
Products: -
Products: -
?
4'-chloroacetophenone + NADH + H+
(S)-1-(4-chlorophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-ethylacetophenone + NADH + H+
(S)-1-(4-ethylphenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-fluoroacetophenone + NADH + H+
(1S)-1-(4-fluorophenyl)ethanol + NAD+
-
Substrates: 117% of the activity with acetophenone
Products: -
Products: -
?
4'-fluoroacetophenone + NADH + H+
(S)-1-(4-fluorophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-hydroxyacetophenone + NADH + H+
(S)-4-(1-hydroxyethyl)phenol + NAD+
-
Substrates: 90% (S)-enantiospecific product
Products: -
Products: -
r
4'-iodoacetophenone + NADH + H+
(1S)-1-(4-iodophenyl)ethanol + NAD+
-
Substrates: 31% of the activity with acetophenone
Products: -
Products: -
?
4'-methoxyacetophenone + NADH + H+
(S)-1-(4-methoxyphenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4'-nitroacetophenone + NADH + H+
(S)-1-(4-nitrophenyl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4-acetylbenzonitrile + NADH + H+
(S)-4-(1-hydroxyethyl)benzonitrile + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4-acetylpyridine + NADH + H+
(S)-1-(pyridin-4-yl)ethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
4-chloro-3-oxobutanoate + NADH + H+
(S)-4-chloro-3-hydroxybutanoate + NAD+
Substrates: -
Products: 99% enantiomeric excess of (S)-enantiomer
Products: 99% enantiomeric excess of (S)-enantiomer
?
4-methylpentan-2-ol + NADP+
4-methylpentan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
4-phenylbutan-2-ol + NADP+
4-phenylbutan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
6-hydroxy-1-indanone + NADH + H+
(S)-2,3-dihydro-1H-indene-1,6-diol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
6-methyl-5-hepten-2-one + NADH + H+
(S)-6-methyl-5-hepten-2-ol + NAD+
Nocardia fusca AKU 2123
-
Substrates: -
Products: 188% of the activity with (RS)-2-hexanol
Products: 188% of the activity with (RS)-2-hexanol
r
acetophenone + NADH + H+
alpha-phenylethanol + NAD+
Substrates: 87% of the activity with phenylacetaldehyde
Products: -
Products: -
?
acetophenone + NADPH + H+
(1S)-1-phenylethanol + NADP+
Substrates: -
Products: -
Products: -
?
alpha-tetralone + NADH + H+
(S)-alpha-tetralol + NAD+
-
Substrates: completely enantioselective reaction
Products: 99% enantiomeric excess after 6 h at 50°C
Products: 99% enantiomeric excess after 6 h at 50°C
r
capronaldehyde + NADH + H+
n-hexanol + NAD+
Substrates: 522% of the activity with phenylacetaldehyde
Products: -
Products: -
?
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
ethyl 4-chloro-3-oxobutanoate + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: -
Products: 38.1% of the activity with (RS)-2-hexanol
Products: 38.1% of the activity with (RS)-2-hexanol
r
ethyl 2-chloro-3-oxobutanoate + NADH + H+
ethyl 2-chloro-3-hydroxybutanoate + NAD+
Substrates: 49% of the activity with ethyl 4-chloro-3-oxobutanoate
Products: -
Products: -
?
ethyl 3-oxobutanoate + NADH + H+
ethyl 3-hydroxybutanoate + NAD+
Substrates: 28% of the activity with ethyl 4-chloro-3-oxobutanoate
Products: -
Products: -
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (S)-3-hydroxybutanoate + NADP+
Substrates: -
Products: -
Products: -
?
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD+
Substrates: -
Products: product in more than 99% enantiomeric excess
Products: product in more than 99% enantiomeric excess
?
heptan-1-ol + NADP+
heptanal + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
heptan-2-ol + NADP+
heptan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
heptan-2-one + NADH + H+
heptan-2-ol + NAD+
Substrates: -
Products: -
Products: -
?
heptan-3-one + NADH + H+
heptan-3-ol + NAD+
Substrates: -
Products: -
Products: -
?
heptan-4-one + NADH + H+
heptan-4-ol + NAD+
Substrates: -
Products: -
Products: -
?
hexan-1-ol + NADP+
hexanal + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
hexan-2-ol + NADP+
hexan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
hexan-2-one + NADH + H+
hexan-2-ol + NAD+
Substrates: -
Products: -
Products: -
?
hexan-3-one + NADH + H+
hexan-3-ol + NAD+
Substrates: -
Products: -
Products: -
?
methyl (4-chlorobenzoyl)acetate + NADH + H+
(S)-methyl 3-(4-chlorophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
methyl 3-(4-ethylphenyl)-3-oxopropanoate + NADH + H+
(S)-methyl 3-(4-ethylphenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
methyl 3-(4-methylphenyl)-3-oxopropanoate + NADH + H+
(S)-methyl 3-hydroxy-3-(4-methylphenyl)propanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
methyl 3-oxo-3-phenylpropanoate + NADH + H+
(S)-methyl 3-hydroxy-3-phenylpropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
methyl 4-bromobenzoylacetate + NADH + H+
(S)-methyl 3-(4-bromophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
methyl 4-chloro-3-oxobutanoate + NADPH + H+
methyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
Products: -
Products: -
?
methyl 4-fluorobenzoylacetate + NADH + H+
(S)-methyl 3-(4-fluorophenyl)-3-hydroxypropanoate + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
n-valeraldehyde + NADH + H+
? + NAD+
Nocardia fusca AKU 2123
-
Substrates: 84% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
nonan-2-one + NADH + H+
nonan-2-ol + NAD+
Substrates: -
Products: -
Products: -
?
nonan-3-one + NADH + H+
nonan-3-ol + NAD+
Substrates: -
Products: -
Products: -
?
nonan-4-one + NADH + H+
nonan-4-ol + NAD+
Substrates: -
Products: -
Products: -
?
nonan-5-one + NADH + H+
nonan-5-ol + NAD+
Substrates: -
Products: -
Products: -
?
octan-1-ol + NADP+
octanal + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
octan-2-ol + NADP+
octan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
octan-3-one + NADH + H+
octan-3-ol + NAD+
Substrates: -
Products: -
Products: -
?
octan-4-one + NADH + H+
octan-4-ol + NAD+
Substrates: -
Products: -
Products: -
?
p-chloro-acetophenone + NADH + H+
alpha-(p-chlorophenyl)ethanol + NAD+
Substrates: 288% of the activity with phenylacetaldehyde
Products: -
Products: -
?
pentan-1-ol + NADP+
pentanal + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
pentan-2-ol + NADP+
pentan-2-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
pentan-2-one + NADH + H+
pentan-2-ol + NAD+
Substrates: -
Products: -
Products: -
?
pentan-3-one + NADH + H+
pentan-3-ol + NAD+
Substrates: -
Products: -
Products: -
?
phenylacetaldehyde + NADH + H+
2-phenylethanol + NAD+
Substrates: -
Products: -
Products: -
?
propiophenone + NADH + H+
(S)-1-phenylpropan-1-ol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
pyruvic acid ethyl ester + NADH + H+
? + NAD+
Nocardia fusca AKU 2123
-
Substrates: 225% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
rac-1-indanol + NAD+
1-indanone + NADH + H+
-
Substrates: 3900% activity compared to (S)-1-phenylethanol
Products: -
Products: -
r
rac-alpha-tetralol + NAD+
alpha-tetralone + NADH + H+
-
Substrates: 2700% activity compared to (S)-1-phenylethanol
Products: -
Products: -
r
valeraldehyde + NADH + H+
n-pentanol + NAD+
Substrates: 433% of the activity with phenylacetaldehyde
Products: -
Products: -
?
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 0.9% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(R)-1-phenylethanol + NAD+
1-phenylethanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 21% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: the enzyme catalyzes the stereospecific oxidation of (S)-1-phenylethanol to acetophenone during anaerobic ethylbenzene mineralization, but also the reverse reaction, i.e. NADH-dependent enantioselective reduction of acetophenone to (S)-1-phenylethanol, high enantioselectivity of the reaction
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Rhodotorula sp. AS2.2241
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Substrates: activity of the wild-type enzyme, the mutant I886A is (R)-specific forming (R)-1-phenylethanol
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: asymmetric reduction of acetophenone to produce (S)-1-phenylethanol, with an enantiomeric excess of more than 99%
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
Substrates: asymmetric reduction of acetophenone to produce (S)-1-phenylethanol, with an enantiomeric excess of more than 99%
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 27% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(S)-2-butanol + NAD+
2-butanone + NADH + H+
-
Substrates: -
Products: -
Products: -
?
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 121% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-2-hexanol + NAD+
2-hexanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: reaction is stereoselective
Products: -
Products: -
r
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
Nocardia fusca AKU 2123
-
Substrates: 91% of the activity with (RS)-2-hexanol
Products: -
Products: -
r
(S)-2-pentanol + NAD+
2-pentanone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
1-indanone + NADH + H+
(S)-1-indanol + NAD+
-
Substrates: -
Products: 99% enantiomeric excess after 6 h at 50°C
Products: 99% enantiomeric excess after 6 h at 50°C
?
1-phenylbutan-1-one + NADH + H+
1-phenylbutan-1-ol + NAD+
Substrates: -
Products: -
Products: -
?
1-phenylbutan-1-one + NADH + H+
1-phenylbutan-1-ol + NAD+
Geotrichum candidum NBRC 4597
Substrates: -
Products: -
Products: -
?
1-phenylheptan-1-one + NADH + H+
1-phenylheptan-1-ol + NAD+
Substrates: -
Products: -
Products: -
?
1-phenylheptan-1-one + NADH + H+
1-phenylheptan-1-ol + NAD+
Geotrichum candidum NBRC 4597
Substrates: -
Products: -
Products: -
?
1-phenylhexan-1-one + NADH + H+
1-phenylhexan-1-ol + NAD+
Substrates: -
Products: -
Products: -
?
1-phenylhexan-1-one + NADH + H+
1-phenylhexan-1-ol + NAD+
Geotrichum candidum NBRC 4597
Substrates: -
Products: -
Products: -
?
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
-
Substrates: 102% of the activity with acetophenone
Products: -
Products: -
?
2'-fluoroacetophenone + NADH + H+
(1S)-1-(2-fluorophenyl)ethanol + NAD+
-
Substrates: 102% of the activity with acetophenone
Products: -
Products: -
?
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
-
Substrates: 102% of the activity with acetophenone
Products: -
Products: -
?
3'-fluoroacetophenone + NADH + H+
(1S)-1-(3-fluorophenyl)ethanol + NAD+
-
Substrates: 102% of the activity with acetophenone
Products: -
Products: -
?
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
-
Substrates: 80% of the activity with acetophenone
Products: -
Products: -
?
4'-acetoxy acetophenone + NADH + H+
(1S)-1-(4-acetoxyphenyl)ethanol + NAD+
-
Substrates: 80% of the activity with acetophenone
Products: -
Products: -
?
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
-
Substrates: 98% of the activity with acetophenone
Products: 102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
Products: 102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
?
4'-acetyl pyridine + NADH + H+
(1S)-1-(pyridin-4-yl)ethanol + NAD+
-
Substrates: 98% of the activity with acetophenone
Products: 102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
Products: 102% of the activity with acetophenone, enantiomeric excess of more than 99% for (S)-configuration of product
?
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
-
Substrates: 82% of the activity with acetophenone
Products: -
Products: -
?
4'-bromoacetophenone + NADH + H+
(1S)-1-(4-bromophenyl)ethanol + NAD+
-
Substrates: 82% of the activity with acetophenone
Products: -
Products: -
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
Substrates: -
Products: enantiomeric excess of more than 99% for (S)-configuration of product
Products: enantiomeric excess of more than 99% for (S)-configuration of product
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
Substrates: -
Products: -
Products: -
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
Geotrichum candidum NBRC 4597
Substrates: -
Products: -
Products: -
?
acetophenone + NADH + H+
(1S)-1-phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
?
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
Substrates: 100% (S)-enantiospecific product
Products: -
Products: -
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
Substrates: completely enantioselective reaction
Products: 99% enantiomeric excess after 6 h at 50°C
Products: 99% enantiomeric excess after 6 h at 50°C
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
r
acetophenone + NADH + H+
(S)-1-phenylethanol + NAD+
-
Substrates: -
Products: -
Products: -
r
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
-
Substrates: -
Products: -
Products: -
r
ethyl 4-chloro-3-oxobutanoate + NADH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate + NAD+
Nocardia fusca AKU 2123
-
Substrates: -
Products: -
Products: -
r
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
Products: the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
Products: the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
Products: the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
Products: the enzyme catalyzes the asymmetric reduction of ethyl 4-chloro-3-oxobutanoate, 99% enantiomeric excess
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
Substrates: -
Products: -
Products: -
?
octan-2-one + NADH + H+
octan-2-ol + NAD+
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: application of PEDH for asymmetric reduction of 42 prochiral ketones and 11 beta-keto esters to enantiopure secondary alcohols, high enantioselectivity of the reaction, substrate binding mechanism analysis by molecular docking, modeling of enzyme-substrate complexes, overview
Products: -
Products: -
?
additional information
?
-
Substrates: no substrates: cetophenone, 2-hydroxyacetophenone, acetone, butanone, 2-pentanone, 3-pentanone, 2-hexanone, 2-heptanone, 2-octanone, cyclohexanone, acetylacetone, 2,5-hexanedione and 5,5-dimethyl-l,3-cyclohexanedione
Products: -
Products: -
?
additional information
?
-
Nocardia fusca AKU 2123
-
Substrates: primary alcohols are not accepted as substrate
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme catalyzes stereoselective oxidation of (S)-secondary alcohols to corresponding ketones
Products: -
Products: -
?
additional information
?
-
Rhodotorula sp. AS2.2241
-
Substrates: the enzyme catalyzes stereoselective oxidation of (S)-secondary alcohols to corresponding ketones
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate specificity of ADHTt in the oxidation and the reduction reactions depends on the substrate, cf. (R)-specific secondary alcohol dehydrogenase, detailed overview. The enzyme shows a high reduction rate with halogenated aryl ketones, such as 2,2,2-trifluoroacetophenone, 2-chloroacetophenone, and 4-chlorobutyrophenone, and with aryl diketones, such as 1-phenyl-1,2-propanedione, although it is not active on benzil, i.e. diphenylethanedione. ADHTt proves to be very effective in reducing aryl alpha-keto esters, although it is not active on aliphatic alpha-keto esters and aryl beta-keto ester. Critical role of the D37 residue in discriminating NAD(H) from NADP(H)
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Rhodotorula sp. AS2.2241
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Substrates: activity of the wild-type enzyme, the mutant I886A is (R)-specific forming (R)-1-phenylethanol
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
-
Substrates: -
Products: -
Products: -
r
(S)-1-phenylethanol + NAD+
acetophenone + NADH + H+
Thermus thermophilus HB27 / ATCC BAA-163 / DSM 7039
-
Substrates: -
Products: -
Products: -
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
critical role of the D37 residue in discriminating NAD(H) from NADP(H)
NADH
-
critical role of the D37 residue in discriminating NAD(H) from NADP(H)
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