Information on EC 1.1.1.184 - carbonyl reductase (NADPH)

Word Map on EC 1.1.1.184
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
1.1.1.184
-
RECOMMENDED NAME
GeneOntology No.
carbonyl reductase (NADPH)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
R-CHOH-R' + NADP+ = R-CO-R' + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
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-
Metabolic pathways
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-
Metabolism of xenobiotics by cytochrome P450
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arachidonic acid metabolism
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-
SYSTEMATIC NAME
IUBMB Comments
secondary-alcohol:NADP+ oxidoreductase
Acts on a wide range of carbonyl compounds, including quinones, aromatic aldehydes, ketoaldehydes, daunorubicin and prostaglandins E and F, reducing them to the corresponding alcohol. Si-specific with respect to NADPH [cf. EC 1.1.1.2 alcohol dehydrogenase (NADP+)].
CAS REGISTRY NUMBER
COMMENTARY hide
77106-95-7
-
89700-36-7
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89700-37-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
putative
UniProt
Manually annotated by BRENDA team
putative
UniProt
Manually annotated by BRENDA team
Candida macedoniensis
-
-
-
Manually annotated by BRENDA team
3alpha-hydroxysteroid dehydrogenase/carbonyl reductase
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-
Manually annotated by BRENDA team
Cylindrocarpon sclerotigenum
enzyme CSCR1, strain IFO 31855
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-
Manually annotated by BRENDA team
strain NCIM 980
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-
Manually annotated by BRENDA team
strain NCIM 980
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-
Manually annotated by BRENDA team
enzyme KLCR1 from strain NRIC 1329
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-
Manually annotated by BRENDA team
predicted; gene nccr; putative
UniProt
Manually annotated by BRENDA team
predicted; gene nccr
UniProt
Manually annotated by BRENDA team
var. dairenensis, IFO415
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-
Manually annotated by BRENDA team
gene Gre2 or YOL151w
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-
Manually annotated by BRENDA team
actIII orf5 gene, ketoreductase type II
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-2-butanol + NADP+
2-butanone + NADPH + H+
show the reaction diagram
(S)-2-butanol + NADP+
2-butanone + NADPH + H+
show the reaction diagram
1,2-naphthoquinone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
1,4-benzoquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
1,4-benzoquinone + NADPH
? + NADP+
show the reaction diagram
-
native and recombinant enzymes, low activity
-
-
?
1,4-naphthoquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
1,4-naphthoquinone + NADPH
? + NADP+
show the reaction diagram
-
native and recombinant enzymes, low activity
-
-
?
1,4-naphthoquinone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanol + NADP+
show the reaction diagram
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanol + NADP+
show the reaction diagram
1-(4-chlorophenyl)ethanone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
show the reaction diagram
1-acetonaphthone + NADPH
? + NADP+
show the reaction diagram
1-acetonaphtone + NADPH + H+
? + NADP+
show the reaction diagram
1-adamantyl methyl ketone + NADPH + H+
1-adamantyl methyl alcohol + NADP+
show the reaction diagram
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
1-butanal + NADPH
1-butanol + NADP+
show the reaction diagram
-
-
-
-
?
1-heptanal + NADPH
1-heptanol + NADP+
show the reaction diagram
-
-
-
-
?
1-hexanal + NADPH
1-hexanol + NADP+
show the reaction diagram
-
-
-
-
?
1-indanone + NADPH
1-indanol + NADP+
show the reaction diagram
-
-
-
-
?
1-methylisatin + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
1-nonanal + NADPH
1-nonanol + NADP+
show the reaction diagram
-
-
-
-
?
1-pentanal + NADPH
1-pentanol + NADP+
show the reaction diagram
-
-
-
-
?
1-phenyl-1,2-propandione + NADPH + H+
(R)-1-phenyl-2-hydroxy-1-propanone + NADP+
show the reaction diagram
1-phenyl-1,2-propandione + NADPH + H+
(S)-1-phenyl-2-hydroxy-1-propanone + NADP+
show the reaction diagram
1-phenyl-1,2-propanedione + NADPH
? + NADP+
show the reaction diagram
-
recombinant enzyme
-
-
?
1-phenylethanone + NADPH + H+
(S)-1-phenylethanol + NADP+
show the reaction diagram
1-phenylisatin + NADPH
? + NADP+
show the reaction diagram
1-propanal + NADPH
1-propanol + NADP+
show the reaction diagram
-
-
-
-
?
13,14-dihydro-15-ketoprostaglandin F2alpha + NADPH
13,14-dihydroprostaglandin F2alpha + NADP+
show the reaction diagram
13-deoxydoxorubicin + NADPH + H+
?
show the reaction diagram
an anthracyclin, formation of a 13-hydroxy-anthracyclin
-
-
?
16-ketoestrone + NADPH
? + NADP+
show the reaction diagram
2 4-fluoroacetophenone + 2 NADPH + 2 H+
(1S)-1-(4-fluorophenyl)ethanol + (1R)-1-(4-fluorophenyl)ethanol + 2 NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 46% enantiomeric excess, mutant Q245H, (S)-configuration with 92%, mutant Q245P, with 90%, mutant Q245L, with 93% enantiomeric excess, respectively
-
?
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
show the reaction diagram
-
-
-
-
?
2'-methoxyacetophenone + NADPH + H+
1-(2-methoxyphenyl)ethanol + NADP+
show the reaction diagram
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
2,2,2-trifluoroacetophenone + NADPH + H+
(1S)-2,2,2-trifluoro-1-phenylethanol + NADP+
show the reaction diagram
2,2,2-trifluoroacetophenone + NADPH + H+
(R)-2,2,2-trifluoro-1-phenylethanol + NADP+
show the reaction diagram
2,2-dimethylcyclohexanone-1,3-dione + NADPH + H+
(S)-3-hydroxy-2,2-dimethylcyclohexanone + NADP+
show the reaction diagram
-
-
-
-
?
2,2-dimethylpropiophenone + NADPH + H+
2,2-dimethylpropiophenol + NADP+
show the reaction diagram
-
-
over 90% chiral purity of the alcohol product
-
?
2,3-bornanedione + NADPH
?
show the reaction diagram
-
-
-
-
?
2,3-butanediol + NADP+
acetoin + NADPH + H+
show the reaction diagram
-
-
-
-
?
2,3-butanedione + NADPH
?
show the reaction diagram
-
-
-
-
?
2,3-butanedione + NADPH
? + NADP+
show the reaction diagram
2,3-butanedione + NADPH + H+
? + NADP+
show the reaction diagram
2,3-heptandione + NADPH + H+
? + NADP+
show the reaction diagram
2,3-heptanedione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
2,3-heptanedione + NADPH + H+
? + NADP+
show the reaction diagram
18.8% of the activity with dihydroxyacetone
-
-
?
2,3-hexadione + NADPH
? + NADP+
show the reaction diagram
-
recombinant enzyme
-
-
?
2,3-hexandione + NADPH + H+
? + NADP+
show the reaction diagram
2,3-hexanedione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
2,3-hexanedione + NADPH + H+
? + NADP+
show the reaction diagram
2,3-pentanedione + NADPH + H+
(R)-2-hydroxy-pentane-3-one + NADP+
show the reaction diagram
2,3-pentanedione + NADPH + H+
(S)-2-hydroxy-pentane-3-one + NADP+
show the reaction diagram
2,3-pentanedione + NADPH + H+
? + NADP+
show the reaction diagram
2,4-octanedione + NADPH + H+
(S)-2-hydroxy-4-octanone + NADP+
show the reaction diagram
-
-
-
-
?
2,5-diketo-D-gluconate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
2-(3,4,6-tri-[3,4,5,6-tetrahydro])phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(3,4,6-tri-[3,4,5,6-tetrahydro])phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(3,5-difluoro)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(3,5-difluoro)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(3-fluoro)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(3-fluoro)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(3-fluoro)phthalimido-methyl-3-oxobutanoate + NADPH
3-hydroxy-2-(3-fluoro)phthalimidomethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(3-methoxy)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(3-methoxy)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(4-fluoro)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(4-fluoro)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(4-methyl)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(4-methyl)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(4-methyl)phthalimido-methyl-3-oxobutanoate + NADPH
3-hydroxy-2-(4-methyl)phthalimidomethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-(4-tert-butyl)phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-(4-tert-butyl)phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-benzoylpyridine + NADPH
(S)-alpha-phenyl-2-pyridylmethanol + NADP+
show the reaction diagram
-
highly stereoselective reaction, native and recombinant enzymes, low activity
-
-
?
2-benzoylpyridine + NADPH
?
show the reaction diagram
-
-
-
-
?
2-bromo-aceto-2-chlorophenone + NADPH
(R)-2-bromo-1-(2-chlorophenyl)ethanol + NADP+
show the reaction diagram
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-aceto-3-chlorophenone + NADPH
(R)-2-bromo-1-(3-chlorophenyl)ethanol + NADP+
show the reaction diagram
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-aceto-4-chlorophenone + NADPH
(R)-2-bromo-1-(4-chlorophenyl)ethanol + NADP+
show the reaction diagram
-
stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-bromo-acetophenone + NADPH
(R)-2-bromo-1-phenylethanol + NADP+
show the reaction diagram
-
i.e. phenacyl bromide, stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-butanol + NADP+
2-butanone + NADPH + H+
show the reaction diagram
2-butanone + NADPH
2-butanol + NADP+
show the reaction diagram
2-chloro-aceto-3-chlorophenone + NADPH
(R)-2-chloro-1-(3-chlorophenyl)ethanol + NADP+
show the reaction diagram
-
i.e. 3-chlorophenacyl chloride
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-chloroacetophenone + NADPH + H+
(R)-2-chloro-1-phenylethanol + NADP+
show the reaction diagram
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzyl alcohol + NADP+
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
2-chlorobenzaldehyde + NADPH + H+
2-chlorobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
2-halo-acetophenone + NADPH
(R)-2-halo-1-phenylethanol + NADP+
show the reaction diagram
-
i.e. phenacyl halide, stereospecific enzyme
product reacts spontaneously to the (R)-styrene oxide derivative in NaOH
-
?
2-heptanone + NADPH
2-heptanol + NADP+
show the reaction diagram
-
-
-
-
?
2-hydroxy-3-butanone + NADPH
2,3-dihydroxybutanol + NADP+
show the reaction diagram
-
-
-
?
2-hydroxyacetophenone + NADH + H+
(S)-1-phenyl-1,2-ethanediol + NAD+
show the reaction diagram
2-hydroxyacetophenone + NADPH + H+
(R)-1-phenyl-1,2-ethanediol + NADP+
show the reaction diagram
2-hydroxyacetophenone + NADPH + H+
(S)-1-phenyl-1,2-ethanediol + NADP+
show the reaction diagram
2-ketopantothenonitrile + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
2-methyl-1,4-benzoquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
2-nitrobenzaldehyde + NADPH
2-nitrobenzyl alcohol + NADP+
show the reaction diagram
2-nitrobenzaldehyde + NADPH
2-nitrobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
2-oxo-4-phenylbutanoate + NADPH + H+
(R)-2-hydroxy-4-phenylbutanoate + NADPH
show the reaction diagram
2-oxobutyric acid + NADPH
2-hydroxybutyric acid + NADP+
show the reaction diagram
-
low activity
-
-
?
2-pentanol + NADP+
2-pentanone + NADPH + H+
show the reaction diagram
-
-
-
-
r
2-pentanone + NADPH
2-pentanol + NADP+
show the reaction diagram
-
-
-
-
?
2-phthalimido-ethyl-3-oxobutanoate + NADPH
3-hydroxy-2-phthalimidoethylbutanoate + NADP+
show the reaction diagram
-
reduction of the beta-keto group to stereospecifically give the (R)-alcohol
-
-
?
2-propanol + NADP+
propanone + NADPH + H+
show the reaction diagram
-
-
2-propanone i.e. acetone
-
r
3,4-hexandione + NADPH + H+
? + NADP+
show the reaction diagram
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
show the reaction diagram
3-benzoylpyridine + NADPH
?
show the reaction diagram
3-chlorobenzaldehyde + NADPH + H+
3-chlorobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+
3-hydroxybenzyl alcohol + NADP+
show the reaction diagram
-
7.1% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
3-nitroacetophenone + NADPH
1-(3-nitrophenyl)ethanol + NADP+
show the reaction diagram
-
-
-
-
?
3-nitroacetophenone + NADPH
?
show the reaction diagram
-
-
-
-
?
3-nitrobenzaldehyde + NADPH
3-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
3-nitrobenzaldehyde + NADPH
3-nitrobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
3-nitrobenzaldehyde + NADPH + H+
3-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
7.0% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
3-oxo-3-(2,4-difluorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(2,4-difluorophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
92% yield, 98% enantiomeric excess
-
?
3-oxo-3-(3-methoxyphenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(3-methoxyphenyl)propanenitrile + NADP+
show the reaction diagram
-
-
89% yield, 97% enantiomeric excess
-
?
3-oxo-3-(3-nitrophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(3-nitrophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
87% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-bromophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-bromophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
88% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-chlorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-chlorophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-cyanophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-cyanophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-fluorophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-fluorophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
90% yield, 99% enantiomeric excess
-
?
3-oxo-3-(4-methylphenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-methylphenyl)propanenitrile + NADP+
show the reaction diagram
-
-
90% yield, 98% enantiomeric excess
-
?
3-oxo-3-(4-nitrophenyl)propanenitrile + NADPH
(R)-3-hydroxy-3-(4-nitrophenyl)propanenitrile + NADP+
show the reaction diagram
-
-
86% yield, 99% enantiomeric excess
-
?
3-oxo-3-phenylpropanenitrile + NADPH
(R)-3-hydroxy-3-phenylpropanenitrile + NADP+
show the reaction diagram
-
-
85% yield, 98% enantiomeric excess
-
?
3alpha-hydroxy-5beta-androstan-17-one + NADPH
?
show the reaction diagram
-
-
-
-
?
4'-chloroacetophenone + NADPH + H+
(S)-1-(4-chlorophenyl)ethanol + NADP+
show the reaction diagram
4-(6-methoxy-2-benzoxazolyl)acetophenone + NADPH
?
show the reaction diagram
-
-
-
-
?
4-acetylpyridine + NADPH
?
show the reaction diagram
-
-
-
-
?
4-acetylpyridine + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
4-benzoylpyridine + NADPH
(S)-alpha-phenyl-4-pyridylmethanol
show the reaction diagram
-
-
-
-
?
4-benzoylpyridine + NADPH
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
show the reaction diagram
4-benzoylpyridine + NADPH
(S)-phenyl(pyridin-4-yl)methanol + NADP+
show the reaction diagram
-
-
-
?
4-benzoylpyridine + NADPH
?
show the reaction diagram
4-benzoylpyridine + NADPH
phenyl-4-pyridylmethanol + NADP+
show the reaction diagram
-
-
-
?
4-benzoylpyridine + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
S-(-)-phenylpyridin-4-yl-methynol + NADP+
show the reaction diagram
-
stereoselective reduction
-
-
?
4-bromoacetophenone + NADPH
(1S)-1-(4-bromophenyl)ethanol (1R)-1-(4-bromophenyl)ethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 42% enantiomeric excess, mutant Q245H, (S)-configuration with 92%, mutant Q245P, with 98%, mutant Q245L, with 97% enantiomeric excess, respectively
-
?
4-bromobenzaldehyde + NADPH + H+
(4-bromophenyl)methanol + NADP+
show the reaction diagram
4-carboxybenzaldehyde + NADPH
4-carboxybenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
reduction of 4-chloro-3-oxobutanoate to ethyl (S)-4-chloro-3-hydroxybutanoate by transformants in an aqueous mono-phase system for 18 h, gives a molar yield of 94% and an optical purity of the (S)-isomer of more than 99% enantiomeric excess
-
-
?
4-chloroacetophenone + NADPH
(1S)-1-(4-chlorophenyl)ethanol (1R)-1-(4-chlorophenyl)ethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 14% enantiomeric excess, mutant Q245H, (S)-configuration with 90%, mutant Q245P, with 96%, mutant Q245L, with 96% enantiomeric excess, respectively
-
?
4-chlorobenzaldehyde + NADPH + H+
(4-chlorophenyl)methanol + NADP+
show the reaction diagram
4-chlorobenzaldehyde + NADPH + H+
4-chlorobenzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-fluorobenzaldehyde + NADPH + H+
(4-fluorophenyl)methanol + NADP+
show the reaction diagram
-
99% conversion
-
-
?
4-hexanoylpyridine + NADPH
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
show the reaction diagram
-
-
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
show the reaction diagram
4-methoxyacetophenone + NADPH
(1S)-1-(4-methoxyphenyl)ethanol + (1R)-1-(4-methoxyphenyl)ethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 57% enantiomeric excess, mutant Q245H, (S)-configuration with 79%, mutant Q245P, with 98%, mutant Q245L, with 96% enantiomeric excess, respectively
-
?
4-methylacetophenone + NADPH
(1S)-1-(4-methylphenyl)ethanol (1R)-1-(4-methylphenyl)ethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 59% enantiomeric excess, mutant Q245H, (S)-configuration with 95%, mutant Q245P, with 96%, mutant Q245L, with 95% enantiomeric excess, respectively
-
?
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH + H+
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
show the reaction diagram
-
i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
-
-
r
4-nitroacetophenone + NADPH
1-(4-nitrophenyl)ethanol + NADP+
show the reaction diagram
-
native and recombinant enzymes, low activity
-
-
?
4-nitroacetophenone + NADPH
?
show the reaction diagram
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
4-nitrobenzaldehyde + NADPH
4-nitrobenzylalcohol + NADP+
show the reaction diagram
4-oxonon-2-enal + NADPH
4-oxononanal + 4-hydroxynon-2-enal + 1-hydroxynon-2-en-4-one + 1,4-dihydroxynon-2-ene + NADP+
show the reaction diagram
-
molecular modeling of substrate binding in the active site
product identification, 4-hydroxynon-2-enal is the major product
-
?
4-oxonon-2-enal + NADPH + H+
1-hydroxynon-2-en-4-one + NADP+
show the reaction diagram
4-oxonon-2-enal + NADPH + H+
4-hydroxynon-2-enal + NADP+
show the reaction diagram
4-oxonon-2-enal + NADPH + H+
4-oxononanal + NADP+
show the reaction diagram
4-pregnen-3,20-dione + NADPH
?
show the reaction diagram
-
isozymes CHCR1-3
-
-
ir
4-tert-butylacetophenone + NADPH
(1S)-1-(4-tert-butylphenyl)ethanol (1R)-1-(4-tert-butylphenyl)ethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 31% enantiomeric excess, mutant Q245H, (S)-configuration with 96%, mutant Q245P, with 99%, mutant Q245L, with 99% enantiomeric excess, respectively
-
?
5-bromoisatin + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH
?
show the reaction diagram
5alpha-androstane-17beta-ol-3-one + NADPH
? + NADP+
show the reaction diagram
5alpha-androstane-3,17-dione + NADPH
?
show the reaction diagram
5alpha-androstane-3,17-dione + NADPH
? + NADP+
show the reaction diagram
5alpha-androstane-3alpha,17beta-diol + NADPH
?
show the reaction diagram
-
isozymes CHCR1-3
-
-
r
5alpha-dihydrotestosterone + NADPH
?
show the reaction diagram
-
only enzyme form CR1
-
-
?
5beta-androstan-17beta-ol-3-one + NADPH
?
show the reaction diagram
5beta-androstane-3,17-dione + NADPH
?
show the reaction diagram
5beta-dihydrotestosterone + NADPH
?
show the reaction diagram
-
only enzyme form CR1
-
-
?
5beta-pregnan-3alpha-ol-20-one + NADPH
? + NADP+
show the reaction diagram
5beta-pregnan-3beta-ol-20-one + NADPH
?
show the reaction diagram
-
isozymes CHCR1-3
-
-
r
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
9,10-phenanthrenequinone + NADPH
? + NADP+
show the reaction diagram
9,10-phenanthrenequinone + NADPH + H+
? + NADP+
show the reaction diagram
9,10-phenanthroline + NADPH + H+
?
show the reaction diagram
-
stereoselective reduction
-
-
?
9-cis-retinal + NADPH
9-cis-retinol + NADP+
show the reaction diagram
-
recombinant enzyme
-
-
?
9-cis-retinal + NADPH
9-cis-retinol + NADPH
show the reaction diagram
-
-
-
-
?
acenaphthenequinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
acetaldehyde + NADPH + H+
ethanol + NADP+
show the reaction diagram
-
-
-
-
?
acetohexamide + NADPH
?
show the reaction diagram
-
-
-
-
?
acetohexamide + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
acetone + NADPH
2-propanol + NADP+
show the reaction diagram
-
-
-
-
?
acetone + NADPH
propan-2-ol + NADP+
show the reaction diagram
acetophenone + NADPH + H+
(1S)-1-phenylethanol + (1R)-1-phenylethanol + NADP+
show the reaction diagram
-
-
wild-type, (R)-configuration of product with 42% enantiomeric excess, mutant Q245H, (S)-configuration with 78%, mutant Q245P, with 64%, mutant Q245L, with 82% enantiomeric excess, respectively
-
?
adrenochrome + NADPH + H+
?
show the reaction diagram
-
stereoselective reduction
-
-
?
all-trans retinal + NADPH + H+
all-trans retinol + NADP+
show the reaction diagram
-
-
-
-
?
all-trans-retinal + NADPH + H+
all-trans-retinol + NADP+
show the reaction diagram
all-trans-retinol + NADP+
all-trans-retinal + NADPH
show the reaction diagram
-
-
-
-
r
alpha-acetoxyacetophenone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
alpha-naphthoquinone + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
alpha-tocopherolquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
befunolol + NADPH
?
show the reaction diagram
-
-
-
-
?
benzalacetone + NADPH
?
show the reaction diagram
-
-
-
-
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
show the reaction diagram
benzaldehyde + NADPH
benzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
benzaldehyde + NADPH + H+
benzyl alcohol + NADP+
show the reaction diagram
benzaldehyde + NADPH + H+
benzylalcohol + NADP+
show the reaction diagram
-
-
-
-
?
benzil + NADPH
? + NADP+
show the reaction diagram
-
recombinant enzyme
-
-
?
benzoylformic acid ethyl ester + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
bupropion + NADPH + H+
erythrohydrobupropion + NADP+
show the reaction diagram
-
-
in liver cytosol, antidepressant bupropion is reduced to erythrohydrobupropion and threohydrobupropion
-
?
bupropion + NADPH + H+
threohydrobupropion + NADP+
show the reaction diagram
-
-
in liver cytosol, antidepressant bupropion is reduced to erythrohydrobupropion and threohydrobupropion
-
?
butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
show the reaction diagram
-
-
-
-
?
butyrophenone + NADPH + H+
(1S)-1-phenylbutan-1-ol + NADP+
show the reaction diagram
-
-
over 90% chiral purity of the alcohol product
-
?
camphorquinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
camphorquinone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
camphorquinone + NADPH + H+
camphorquinol + NADP+
show the reaction diagram
-
-
-
-
?
carnitine + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
chloromethyl 3-oxobutyrate + NADPH + H+
chloromethyl (S)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
97% purity of the S-enantiomer
-
?
crotonaldehyde + NADPH
2-buten-1-ol + NADP+
show the reaction diagram
-
-
-
-
?
cycloheptanone + NADPH + H+
cycloheptanol + NADP+
show the reaction diagram
-
-
-
-
?
cyclohex-2-en-3-ol + NADPH
cyclohex-2-en-3-one + NADP+
show the reaction diagram
-
-
-
-
?
cyclohexanol + NADP+
cyclohexanone + NADPH + H+
show the reaction diagram
-
-
-
-
r
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
cyclopentanol + NADP+
cyclopentanone + NADPH + H+
show the reaction diagram
-
-
-
-
r
cyclopentanone + NADPH
cyclopentanol + NADP+
show the reaction diagram
-
low activity
-
-
?
D-xylose + NADPH
? + NADP+
show the reaction diagram
Cylindrocarpon sclerotigenum
-
very low activity
-
-
ir
daunorubicin + NADPH
?
show the reaction diagram
daunorubicin + NADPH
daunorubicinol + NADP+
show the reaction diagram
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
decanal + NADPH
decanol + NADP+
show the reaction diagram
-
-
-
-
?
DELTA4-androstan-17beta-ol-3-one + NADPH
?
show the reaction diagram
-
isozymes CHCR1-3
-
-
r
diacetyl + NADPH
?
show the reaction diagram
-
-
-
-
?
diacetyl + NADPH
? + NADP+
show the reaction diagram
diacetyl + NADPH + H+
(3S)-acetoin + NADP+
show the reaction diagram
diacetyl + NADPH + H+
acetoin + NADP+
show the reaction diagram
dihydrokawain + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
dihydroxyacetone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
dihydroxyacetone + NADPH + H+
glycerol + NADP+
show the reaction diagram
doxorubicin + NADPH
doxorubicinol + NADP+
show the reaction diagram
-
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
show the reaction diagram
duroquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 2-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
135.7% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
ethyl 2-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
-
-
-
?
ethyl 2-chloro-3-oxobutanoate + NADPH + H+
ethyl-2-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
-
-
-
?
ethyl 2-ketopantothenate + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
ethyl 2-methyl-3-oxobutanoate + NADPH + H+
ethyl 3-hydroxy-2-methylbutanoate + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-methylacetoacetate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-oxo-3-phenylpropanoate + NADPH + H+
ethyl 2-hydroxy-3-phenylpropanoate + NADP+
show the reaction diagram
128% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 2-oxo-3-phenylpyruvate + NADPH + H+
ethyl 2-hydroxy-3-phenylpyruvate + NADPH
show the reaction diagram
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (2S)-2-hydroxy-4-phenylbutanoate + NADP+
show the reaction diagram
ethyl 2-oxo-4-phenylbutanoate + NADPH + H+
ethyl (R)-2-hydroxy-4-phenylbutanoate + NADPH
show the reaction diagram
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-oxo-4-phenylbutyrate + NADPH + H+
ethyl 2-hydroxy-4-phenylbutyrate + NADP+
show the reaction diagram
ethyl 2-oxophenylacetate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 2-oxopropanoate + NADPH + H+
ethyl 2-hydroxypropanoate + NADP+
show the reaction diagram
41% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
ethyl 3,3-dimethyl-2-oxobutanoate + NADPH + H+
ethyl 3,3-dimethyl-2-hydroxybutanoate + NADP+
show the reaction diagram
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
ethyl 3,3-dimethyl-2-oxobutyrate + NADPH + H+
(S)-ethyl 3,3-dimethyl-2-hydroxybutyrate + NADP+
show the reaction diagram
-
stereoselective reaction
over 90% chiral purity of the alcohol product
-
?
ethyl 3-methyl-2-oxobutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 3-methyl-2-oxobutanoate + NADPH + H+
ethyl (2R)-2-hydroxy-3-methylbutanoate + NADP+
show the reaction diagram
-
95% conversion, 98.3% enantiomeric excess
-
?
ethyl 3-oxo-3-phenylpropionate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 3-oxobutanoate + NADPH
ethyl 3-hydroxybutanoate + NADP+
show the reaction diagram
-
-
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 3-oxobutanoate + NADPH + H+
ethyl (3S)-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 3-oxobutanoate + NADPH + H+
ethyl 3-hydroxybutanoate + NADP+
show the reaction diagram
-
25.2% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
ethyl 3-oxobutyrate + NADPH + H+
ethyl (R,S)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
61% S-enantiomer
-
?
ethyl 3-oxopentanoate + NADPH + H+
ethyl (R,S)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
61% S-enantiomer
-
?
ethyl 3-oxopentanoate + NADPH + H+
ethyl (S)-3-hydroxypentanoate + NADP+
show the reaction diagram
-
-
99% conversion, 99% enantiomeric excess
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
ethyl (3R)-4,4,4-trifluoro-3-hydroxybutanoate + NADP+
show the reaction diagram
74% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl 4,4,4-trifluoro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4,4,4-trifluoro-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
90% purity of the S-enantiomer
-
?
ethyl 4,4-dimethyl-3-oxopentanoate + NADPH + H+
ethyl 4,4-dimethyl-3-hydroxypentanoate + NADP+
show the reaction diagram
-
reduction of the sterically bulky ketone to the corresponding alcohol with excellent optical purity
-
-
?
ethyl 4-chloro-3-oxobutanoate + NAD(P)H + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NAD(P)+
show the reaction diagram
ethyl 4-chloro-3-oxobutanoate + NADPH
ethyl-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
the enantioselectivity of NcCR for the reduction of ethyl 4-chloro-3-oxobutanoate shows a strong dependence on temperature. The enantiomeric excess is substantially increased by decreasing the temperature from 40°C (78.8%) to -3°C (98.0%)
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-ethyl 4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3R)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
8776% of the activity with 2-chloroacetophenone
100% conversion, 62% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (3S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
enantioselectivity shows a strong dependence on temperature. Under optimal conditions of -3°C, (S)-4-chloro-3-hydroxybutanoate in 98% enantiomeric excess is produced
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (R)-4-chloro-3-hydroxybutanoate
show the reaction diagram
-
99% conversion, 92% enantiomeric excess
99% conversion, 92% enantiomeric excess
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl 4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 4-chloroacetoacetate + NADPH + H+
? + NADPH
show the reaction diagram
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 5-oxohexanoate + NADPH
ethyl-5-hydroxyhexanoate + NADP+
show the reaction diagram
-
-
-
-
?
ethyl acetoacetate + NADPH
? + NADP+
show the reaction diagram
-
-
-
?
ethyl benzoylformate + NADPH
? + NADP+
show the reaction diagram
-
-
-
?
ethyl benzoylformate + NADPH + H+
? + NADPH
show the reaction diagram
ethyl pyruvate + NADPH + H+
2-hydroxypropanoic acid + NADP+
show the reaction diagram
-
-
-
-
?
ethyl pyruvate + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
ethyl pyruvate + NADPH + H+
ethyl (2S)-2-hydroxypropanoate + NADP+
show the reaction diagram
7821% of the activity with 2-chloroacetophenone
100% conversion, 99% enantiomeric excess
-
?
ethyl pyruvate + NADPH + H+
ethyl lactate + NADP+
show the reaction diagram
-
-
-
?
ethylpyruvate + NADPH
? + NADP+
show the reaction diagram
Cylindrocarpon sclerotigenum
-
low activity
-
-
ir
fluoxetine + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
glutaraldehyde + NADPH
? + NADP+
show the reaction diagram
-
low activity
-
-
?
glutathione-4-oxonon-2-enal + NADPH
glutathione-4-oxononanal + NADP+
show the reaction diagram
-
conjugate, molecular modeling of substrate binding in the active site
-
-
?
glutathione-4-oxonon-2-enal + NADPH + H+
glutathione-4-hydroxynon-2-enal + NADP+
show the reaction diagram
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
show the reaction diagram
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
show the reaction diagram
hexaphenone + NADPH
1-phenylhexan-1-ol + NADP+
show the reaction diagram
-
native and recombinant enzymes
-
-
?
hydrindantin + NADPH
?
show the reaction diagram
-
-
-
-
?
hydroxyacetone + NADPH
? + NADP+
show the reaction diagram
Cylindrocarpon sclerotigenum
-
low activity
-
-
ir
hydroxyacetone + NADPH + H+
glycerol + NADP+
show the reaction diagram
-
-
-
?
indole 3-acetaldehyde + NADPH
indole-3-ol + NADP+
show the reaction diagram
-
-
-
-
?
isatin + NADPH
?
show the reaction diagram
isatin + NADPH
? + NADP+
show the reaction diagram
isatin + NADPH + H+
3-hydroxy-2-oxoindole + NADP+
show the reaction diagram
isatin + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
isoamyl pyruvate + NADPH + H+
isoamyl lactate + NADP+
show the reaction diagram
-
-
-
?
isopropyl 2-ketopantothenate + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
isopropyl 3-oxobutyrate + NADPH + H+
isopropyl (S)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
99% purity of the S-enantiomer
-
?
ketopantoyl lactone + NADPH
(R)-pantolactone + NADP+
show the reaction diagram
-
-
-
-
?
ketopantoyl lactone + NADPH
?
show the reaction diagram
loxoprofen + NADPH
?
show the reaction diagram
-
-
-
-
?
menadione + NADPH
?
show the reaction diagram
menadione + NADPH
? + NADP+
show the reaction diagram
menadione + NADPH + H+
?
show the reaction diagram
menadione + NADPH + H+
? + NADP+
show the reaction diagram
methyl 2-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 2-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
methyl 2-ketopantothenate + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
methyl 2-oxo-3-phenylpropanoate + NADPH + H+
methyl 2-hydroxy-3-phenylpropanoate + NADP+
show the reaction diagram
-
86.3% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl 2-oxo-4-phenylbutanoate + NADPH + H+
methyl (R)-2-hydroxy-4-phenylbutanoate + NADPH
show the reaction diagram
-
88.5% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl 2-oxopropanoate + NADPH + H+
methyl (2S)-2-hydroxypropanoate + NADP+
show the reaction diagram
-
67% conversion, 99.9% enantiomeric excess
-
?
methyl 4-chloro-3-oxobutanoate + NADPH + H+
(S)-methyl 4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
25.4% of the activity with ethyl 4-chloro-3-oxobutanoate
-
-
?
methyl 4-chloroacetoacetate + NADPH
methyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
highly enantioselective reduction
-
-
ir
methyl benzoylformate + NADPH + H+
? + NADPH
show the reaction diagram
-
79.4% of the activity with ethyl 2-oxo-4-phenylbutanoate
-
-
?
methyl glyoxal + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
methyl pyruvate + NADPH
methyl lactate + NADP+
show the reaction diagram
-
-
-
-
?
methyl-1,4-benzoquinone + NADPH
?
show the reaction diagram
-
-
-
-
?
methyl-2-oxobutanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
methyl-2-oxopropanoate + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
methylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
methylglyoxal + NADPH
? + NADP+
show the reaction diagram
-
very low activity
-
-
ir
methylglyoxal + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
mitroxantrone + NADPH + H+
?
show the reaction diagram
N,N-dimethyl-3-keto-2-thienyl-propanamine + NADPH
(S)-N,N-dimethyl-3-keto-2-thienyl-propanamine + NADP+
show the reaction diagram
-
-
key intermediate in synthesis of (S)-duloxetine
-
?
n-butylaldehyde + NADPH
n-butanol + NADP+
show the reaction diagram
-
-
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
show the reaction diagram
n-hexylaldehyde + NADPH
n-hexanol + NADP+
show the reaction diagram
-
low activity
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
naphthazarin + NADPH + H+
?
show the reaction diagram
nonanophenone + NADPH
1-phenylnonan-1-ol + NADP+
show the reaction diagram
-
recombinant enzyme
-
-
?
octanal + NADPH + H+
1-octanol + NADP+
show the reaction diagram
-
-
-
-
?
octyl 4-chloro-3-oxobutanoate + NADPH
octyl 4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
-
-
-
?
octyl 4-chloro-3-oxobutanoate + NADPH
octyl-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
oracin + NADPH + H+
dihydrooracin + NADP+
show the reaction diagram
oxalacetic acid + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
p-toluquinone + NADPH
?
show the reaction diagram
Candida macedoniensis
-
-
-
-
?
phenyl 3-oxobutyrate + NADPH + H+
phenyl (S,R)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
56% S-enantiomer
-
?
phenyl cyclopropyl ketone + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
phenylglyoxal + 2 NADPH + 2 H+
(R)-1-phenyl-1,2-ethanediol + 2 NADP+
show the reaction diagram
-
-
99% yield and 99% enantiomeric excess, by coupling with D-glucose dehydrogenase for the regeneration of cofactor NADPH
-
?
phenylglyoxal + NADPH
?
show the reaction diagram
phenylglyoxal + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
polyketid + NADPH
?
show the reaction diagram
-
enzyme acts on the nascent polyketid chain from polyketid synthase reaction and reduces the carbonyl group at C-9
-
-
?
propanal + NADPH + H+
propan-1-ol + NADP+
show the reaction diagram
54% of the activity with ethyl 2-methyl-3-oxobutanoate
-
-
?
propionaldehyde + NADPH
propanol + NADP+
show the reaction diagram
-
low activity
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
show the reaction diagram
prostaglandin A-GSH + NADPH
?
show the reaction diagram
prostaglandin A1 + NADPH
?
show the reaction diagram
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin A2 + NADPH
?
show the reaction diagram
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin B2 + NADPH
?
show the reaction diagram
prostaglandin D2 + NADPH
?
show the reaction diagram
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
prostaglandin E2 + NADPH
?
show the reaction diagram
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
prostaglandin F2alpha + NADPH
?
show the reaction diagram
-
isozymes CHCR1 and 2, no activity with isozyme CHCR3
-
-
r
pyrenophorin + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
pyridin-4-carboxyaldehyde + NADPH
pyridin-4-ylmethanol + NADP+
show the reaction diagram
-
artificial substrate
-
-
?
pyridine-3-aldehyde + NADPH
?
show the reaction diagram
pyridine-3-aldehyde + NADPH
pyridin-3-ylbutanol + NADP+
show the reaction diagram
-
native and recombinant enzymes, low activity
-
-
?
pyridine-4-aldehyde + NADPH
?
show the reaction diagram
pyridine-4-aldehyde + NADPH
pyridin-4-ylbutanol + NADP+
show the reaction diagram
-
native and recombinant enzymes
-
-
?
pyridine-4-aldehyde + NADPH
pyridin-4-ylmethanol + NADP+
show the reaction diagram
pyridine-4-carboxaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
S-1-phenyl-1-butanol + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
S-nitrosoglutathione + NADPH + H+
? + NADP+
show the reaction diagram
tert-butyl 3-oxobutyrate + NADPH + H+
tert-butyl (S)-3-hydroxybutyrate + NADP+
show the reaction diagram
-
-
99% purity of the S-enantiomer
-
?
testosterone + NADPH
?
show the reaction diagram
-
-
-
-
?
trans-4-phenyl-3-buten-2-one + NADPH
trans-4-phenyl-3-buten-2-ol + NADP+
show the reaction diagram
-
also reacts with NADH, produces only R-enatiomer
-
-
?
ubiquinone-1 + NADPH
?
show the reaction diagram
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
show the reaction diagram
xestospongin A + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
13,14-dihydro-15-ketoprostaglandin F2alpha + NADPH
13,14-dihydroprostaglandin F2alpha + NADP+
show the reaction diagram
4-benzoylpyridine + NADPH + H+
S-(-)-phenylpyridin-4-yl-methynol + NADP+
show the reaction diagram
-
stereoselective reduction
-
-
?
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH + H+
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
show the reaction diagram
-
i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
-
-
r
4-oxonon-2-enal + NADPH + H+
1-hydroxynon-2-en-4-one + NADP+
show the reaction diagram
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
4-oxonon-2-enal + NADPH + H+
4-hydroxynon-2-enal + NADP+
show the reaction diagram
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
4-oxonon-2-enal + NADPH + H+
4-oxononanal + NADP+
show the reaction diagram
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
all-trans retinal + NADPH + H+
all-trans retinol + NADP+
show the reaction diagram
-
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
P16152
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
doxorubicin + NADPH + H+
doxorubicinol + NADP+
show the reaction diagram
P16152
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
ethyl 4-chloro-3-oxobutanoate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
ethyl 4-chloroacetoacetate + NADPH + H+
ethyl (S)-4-chloro-3-hydroxybutanoate + NADP+
show the reaction diagram
-
enantioselective reduction
-
-
ir
glutathione-4-oxonon-2-enal + NADPH + H+
glutathione-4-hydroxynon-2-enal + NADP+
show the reaction diagram
-
metabolic inactivation of the lipid peroxidation product, pathway overview
-
-
?
menadione + NADPH + H+
?
show the reaction diagram
P16152
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
mitroxantrone + NADPH + H+
?
show the reaction diagram
P16152
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
naphthazarin + NADPH + H+
?
show the reaction diagram
P16152
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
oracin + NADPH + H+
dihydrooracin + NADP+
show the reaction diagram
-
a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation of the anti-cancer drug
-
-
r
prostaglandin E2 + NADPH
prostaglandin F2alpha + NADP+
show the reaction diagram
additional information
?
-