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1.1.1.184: carbonyl reductase (NADPH)

This is an abbreviated version!
For detailed information about carbonyl reductase (NADPH), go to the full flat file.

Word Map on EC 1.1.1.184

Reaction

R-CHOH-R'
+
NADP+
=
R-CO-R'
+
NADPH
+
H+

Synonyms

(R) specific carbonyl reductase, (S)-specific carbonyl reductase, 15-hydroxyprostaglandin dehydrogenase [NADP+], 2,5-diketo-D-gluconic acid reductase, Adipocyte P27 protein, aldehyde reductase 1, aldehyde reductase I, aldo-keto reductase, ALR3, AP27, carbonyl reductase, carbonyl reductase (NADPH), carbonyl reductase 1, carbonyl reductase 3, carbonyl reductase S1, CBR, CBR 1, CBR 3, CBR1, CBR3, CHCR, CHCR1, CHCR2, CHCR3, CR, CR125, crc1, CSCR1, Gox0644, Gox1615, hCBR1, ketoreductase, KLCR1, KR, LCR, LOC415661, LOC610164, microsomal carbonyl reductase, More, NADP+-dependent ADH, NADPH-carbonyl reductase, NADPH-dependent carbonyl reductase, NADPH-dependent carbonyl reductase S1, NCCR, nonspecific NADPH-dependent carbonyl reductase, peroxisomal-type carbonyl reductase, PHCR, prostaglandin 9-ketoreductase, Prostaglandin-E2 9-reductase, PTCR, R-specific carbonyl reductase, reductase S1, reductase, carbonyl, RLCR, SCR, SCR9, SDR21C1, secondary-alcohol: NADP+-oxidoreductase, short-chain (S)-1-phenyl-1,2-ethanediol dehydrogenase, short-chain carbonyl reductase, sniffer, SRED, SSCR, SyS1, tetrameric carbonyl reductase, Tm1743, Tm_1743, xenobiotic carbonyl reductase, xenobiotic ketone reductase, YGL039w1, YGL039w2, YtbE, YueD

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.184 carbonyl reductase (NADPH)

Natural Substrates Products

Natural Substrates Products on EC 1.1.1.184 - carbonyl reductase (NADPH)

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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(4S)-3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone + NADPH + H+
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one + NADP+
show the reaction diagram
-
99.1% conversion
-
-
?
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-nitrobenzaldehyde + NADPH + H+
4-nitrobenzylalcohol + NADP+
show the reaction diagram
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
-
-
-
-
?
cortisol + NADPH + H+
20beta-dihydrocortisol + NADP+
show the reaction diagram
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
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
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
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
reduction of the anthracycline C13 carbonyl results in a 13-hydroxy metabolite that elicits potent cardiotoxic effects while possessing significantly reduced anticancer properties
-
-
?
N,N-dimethyl-3-keto-3-(2-thienyl)-1-keto propanamine + NADPH + H+
(S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol + NADP+
show the reaction diagram
-
mutant enzyme A89N/F154Y with yield of 91.2% and S-enantiomeric excess of 99.9%
-
-
?
naphthazarin + NADPH + H+
?
show the reaction diagram
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
?
-