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.

Reaction

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

Synonyms

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, CSCR1, Gox0644, Gox1615, ketoreductase, KLCR1, KR, LCR, 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, SDR21C1, secondary-alcohol: NADP+-oxidoreductase, short-chain (S)-1-phenyl-1,2-ethanediol dehydrogenase, short-chain carbonyl reductase, sniffer, SSCR, Tm1743, Tm_1743, xenobiotic carbonyl reductase, xenobiotic ketone reductase, YtbE

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)

Inhibitors

Inhibitors on EC 1.1.1.184 - carbonyl reductase (NADPH)

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-1-(2,4-dihydroxyphenyl)-3-(2',4',6-trihydroxy-5'-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]biphenyl-3-yl)prop-2-en-1-one
-
1,10-phenanthroline
14,16-dihydroxy-3,8-dimethyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione
-
zearalenone analogue
18beta-glycyrrhetinic acid
-
inhibits the reduction of bupropion in liver microsomes
2,3,4-trinitrobenzenesulfonate sodium
-
acts on a catalytic lysine located at the cofactor binding site, rapid inactivation of the liver enzyme, kinetics, NADP+, 2'-AMP, 2',5'-ADP, and 2'-phospho-5'-ADP-ribose partly protect, but 4-acetylpyridine, 5'-AMP, 5'-ADP, NMN and NAD+ do not
2,3-Butanedione
-
irreversible inactivation
2,4-dinitrophenol
2,4-Dinitrophenylhydrazine
-
1mM, 0.9% residual activity
2-mercaptoethanol
2-nitrobenzoate
-
1mM, 8.6% residual activity
21-Hydroxy-5alpha-pregnane-3,20-dione
-
-
3',4',7-tris[O-(2-hydroxyethyl)]rutin
-
-
3,3-Tetramethyleneglutaric acid
-
enzyme form CR2 inhibited, CR1 slightly
3-(2-(2,4-dihydroxyphenyl)-1-[hydroxy(4-hydroxyphenyl)methyl]-2-oxoethyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
3-[2,3-dihydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one
-
3-[2-(2,4-dihydroxyphenyl)-1-(4-hydroxybenzyl)-2-oxoethyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
4 methylpyrazole
-
2 mM, 17% inhibition
4-amino-1-tert-butyl-3-(2-hydroxyphenyl)pyrazolo[3,4-d]pyrimidine
-
-
4-hydroxymercuribenzoate
-
0.025 mM, complete inhibition
4-Oxo-4H-benzopyran-2-carboxylic acid
-
-
4-oxonon-2-enal
-
the substrate is also a mechanism-based inhibitor of the enzyme resulting in 50% inactivation of the enzyme-NADPH complex, presence of cofactor is required for inhibition
5,5 dithiobis(2-nitrobenzoate)
-
-
5beta-androstane-3alpha,17beta-diol
-
-
5beta-cholanoic acid
-
-
5beta-pregnane-3,20-dione
-
-
7-monohydroxyethylrutoside
-
inhibits the activity of CBR1 V88 and CBR1 I88 in a concentration-dependent manner. It acts as a competitive CBR1 inhibitor when using daunorubicin as a substrate and acts as an uncompetitive CBR1 inhibitor for the small quinone substrate menadione. It inhibits the binding of NADPH in an uncompetitive manner for both substrates
7-O-beta-D-glucopyranos2-ulosyl-quercetin
-
9,10-phenanthroline
-
strong inhibition
Acetylsalicylate
-
IC50 for the 3 isozymes CHCR1-3, overview
AgNO3
Ammonium molybdate
-
enzyme form CR1 inhibited, CR2 not
androsterone
-
CR2 inhibited, CR1 not
ascorbic acid
-
1mM, 14% residual activity
Barbital
Benzamide
Biochanin A
-
-
bromosulfophthalein
-
-
butyrophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
chlorogenic acid
-
-
chlorpromazine
chrysin
-
-
cibacron
-
IC50 for the 3 isozymes CHCR1-3, overview
Cibacron blue
citrate
-
1mM, 48.3% residual activity
Co2+
Candida macedoniensis
-
-
coumarin
-
-
CuCl2
-
only enzyme forms CR2, CR3
D-catechin
-
-
Dehydrolithocholic acid
-
-
dicoumarol
diethyldicarbonate
-
1mM, 32.8% residual activity
Diphenylhydantoin
-
68% inhibition at 0.5 mM
Disulfiram
-
-
dithiothreitol
EDTA
Cylindrocarpon sclerotigenum
-
30% inhibition at 1 mM
Ethacrynic acid
Fe3+
-
1mM, 29% residual activity
FeSO4
flavonoids
Flufenamic acid
-
-
Furosemide
-
inhibition of V1, V2 and T3
genistein
glycyrrhetinic acid
-
inhibits both 11beta-hydroxysteroid dehydrogenase and carbonyl reductase activities of the enzyme potently
heptanophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
hexanophenone
-
competitive. Inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
hydroxylamine
-
1mM, 29.5% residual activity
Hydroxyquinoline
-
1mM, 45% residual activity
indomethacin
iodoacetamide
-
46% inhibition at 1 mM
iodoacetate
Isobutyramide
-
-
kaempferol
L-cysteine
-
1mM, 18.5% residual activity
lithocholic acid
-
-
megestrol acetate
-
IC50 for the 3 isozymes CHCR1-3, overview
menadione
-
inhibits the reduction of bupropion in liver cytosol
Methyl vinyl ketone
-
74% inhibition at 10 mM
methyltestosterone
-
IC50 for the 3 isozymes CHCR1-3, overview
myristic acid
N-ethylmaleimide
NADP+
NADPH
-
competitive to NADH
naringenin
-
-
NEM
-
30% inhibition at 1 mM
nicotinic acid
-
weak
Norethindrone
-
IC50 for the 3 isozymes CHCR1-3, overview
o-phenanthroline
-
about 11% inhibition at 1 mM
oxalate
-
1mM, 42.8% residual activity
p-chloromercuribenzoate
p-hydroxymercuribenzoate
Pb2+
Candida macedoniensis
-
-
Phenylglyoxal
phenylpyruvic acid
-
-
PMSF
-
about 10% inhibition at 1 mM
progesterone
-
-
propiophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
pyrazole
pyruvate
-
inactivation of isozyme CHCR2, not of isozymes CHCR1 and 3
quercetin
quercitrin
Retin
-
-
-
S-nitrosoglutathione
Sn2+
Candida macedoniensis
-
-
sodium dodecylsulfate
-
0.1% w/v, complete loss of activity
Sodium phenobarbitone
-
enzyme form CR2 inhibited, CR1 slightly
testosterone
-
-
Tetramethyleneglutaric acid
-
-
triclosan
-
-
Triton X-100
-
1% v/v, 88% residual activity
valerophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
Valproic acid
-
-
warfarin
-
IC50 for the 3 isozymes CHCR1-3, overview
wedelolactone
-
-
additional information
-