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(S)-1-indanol + NADP+
?
-
Substrates: -
Products: -
?
(S)-1-tetralol + NADP+
?
-
Substrates: -
Products: -
?
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
(S)-tetralol + NAD(P)+
3,4-dihydronaphthalen-1(2H)-one + NAD(P)H + H+
Substrates: -
Products: -
?
1,2-cyclohexanedione + NADP+
?
1,2-cyclohexanedione + NADPH + H+
?
-
Substrates: -
Products: -
r
1-acenaphthenol + NAD+
? + NADH + H+
Substrates: -
Products: -
?
1-phenyl-1,2-propanedione + NADPH
NADP+ + ?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
11-deoxycortisol + NADH
? + NAD+
11-deoxycortisol + NADH + H+
? + NAD+
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,21-dihydroxy-5beta-pregnan-3,20-dione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3-one + NADP+
-
Substrates: -
Products: -
r
17alpha,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3,11-dione + NADP+
-
Substrates: -
Products: -
r
17alpha,21-dihydroxyadrenocorticosteroid + NAD(P)H
? + NADP+
-
Substrates: NADH preferred
Products: -
?
17alpha-hydroxy-progesterone + NADH + H+
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD+
-
Substrates: -
Products: -
r
17alpha-hydroxycorticosterone + NADPH
? + NADP+
-
Substrates: less reactive than with 17alpha-hydroxyrogesterone
Products: -
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
17beta-estradiol + NADP+
?
-
Substrates: -
Products: -
?
2,3-butanedione + NADPH
? + NADP+
2,3-heptanedione + NADPH
NADP+ + ?
2,3-hexanedione + NADPH
NADP+ + ?
2,3-pentanedione + NADPH
NADP+ + ?
2,4-pentanedione + NADP+
?
2,4-pentanedione + NADPH + H+
4-hydroxypentan-2-one + NADP+
-
Substrates: -
Products: -
r
2-amino-8-((2-fluoro-4-methoxybenzyl)thio)-1,9-dihydro-6H-purin-6-one + NADP+
?
-
Substrates: -
Products: -
r
2-tert-butyl-1,4-benzoquinone + NADPH + H+
?
-
Substrates: -
Products: -
?
20alpha-dihydroprogesterone + NAD+
progesterone + NADH
-
Substrates: -
Products: -
?
20alpha-dihydroprogesterone + NADP+
progesterone + NADPH
-
Substrates: -
Products: -
?
20alpha-hydroxy-5alpha-pregnan-3-one + NADPH + H+
5alpha-pregnan-20alpha,3alpha-diol + NADP+
-
Substrates: -
Products: -
r
20alpha-hydroxy-5beta-pregnan-3-one + NADP+
5beta-pregnane-3,20-dione + NADPH
-
Substrates: -
Products: -
?
20alpha-hydroxypregn-4-en-3-one + 3-acetylpyridine adenine dinucleotide phosphate
?
-
Substrates: -
Products: -
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide 1,N6-ethenoadenine dinucleotide phosphate
?
-
Substrates: -
Products: -
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide hypoxanthine dinucleotide phosphate
?
-
Substrates: -
Products: -
r
20alpha-hydroxypregn-4-en-3-one + thionicotinamide adenine dinucleotide phosphate
?
-
Substrates: -
Products: -
r
20alpha-hydroxyprogesterone + NAD+
progesterone + NADH
-
Substrates: -
Products: -
?
20alpha-hydroxyprogesterone + NADP+
?
-
Substrates: -
Products: -
?
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
3,4-hexanedione + NADP+
?
3-deoxyglucosone + NADPH + H+
?
-
Substrates: -
Products: -
?
3alpha-hydroxy-5-alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
Substrates: -
Products: -
r
3alpha-hydroxy-5alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
Substrates: -
Products: -
r
4-androstene-3,17-dione + NADPH + H+
?
-
Substrates: -
Products: -
?
4-chromanol + NADP+
?
-
Substrates: -
Products: -
?
4-hydroxy-2-nonenal + NADPH + H+
?
-
Substrates: -
Products: -
?
4-nitroacetophenone + NADPH + H+
?
-
Substrates: -
Products: -
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
4-oxo-2-hexenal + NADPH + H+
?
-
Substrates: -
Products: -
?
4-oxo-2-nonenal + NADPH + H+
?
-
Substrates: -
Products: -
?
4-pregnen-20alpha-ol-3-one + NAD(P)+
4-pregnen-3,20-dione + NAD(P)H + H+
-
Substrates: -
Products: -
r
4-pregnen-3alpha-ol-20-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5-androstene-3beta,17beta-diol + NADP+
?
-
Substrates: -
Products: -
?
5alpha-androstan-3alpha,17beta-diol + NADP+
?
-
Substrates: -
Products: -
?
5alpha-androstan-3alpha-ol-17-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-androstan-3beta,17beta-diol + NADP+
?
-
Substrates: -
Products: -
?
5alpha-androstan-3beta-ol-17-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
5alpha-dihydrotestosterone + NADP+
?
-
Substrates: -
Products: -
?
5alpha-dihydrotestosterone + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-dihydrotestosterone + NADPH + H+
? + NADP+
-
Substrates: -
Products: -
?
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H
-
Substrates: -
Products: -
r
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnane-3,20-dione + NAD(P)H
-
Substrates: -
Products: -
r
5alpha-pregnan-20alpha-ol-3-one + NADP+
5beta-pregnan-3,20-dione + NADPH + H+
-
Substrates: -
Products: -
r
5alpha-pregnan-20alpha-ol-3-one + NADP+
?
-
Substrates: -
Products: -
?
5alpha-pregnan-3,20-dione + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-pregnan-3alpha,20alpha-diol + NADP+
?
-
Substrates: -
Products: -
?
5alpha-pregnan-3alpha,21-diol-20-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
Substrates: -
Products: -
r
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
Substrates: -
Products: -
r
5alpha-pregnan-3alpha-ol-20-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5alpha-pregnane-21-ol-3,20-dione + NAD(P)H
5alpha-pregnane-20alpha,21-diol-3-one + NAD(P)+
-
Substrates: -
Products: -
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
Substrates: -
Products: -
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,21-diol-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,20alpha,21-triol + NAD(P)+
-
Substrates: -
Products: -
r
5beta-androstan-17beta-ol-3-one + NADP+
?
-
Substrates: -
Products: -
?
5beta-androstan-3alpha,17beta-diol + NADP+
?
-
Substrates: -
Products: -
?
5beta-androstan-3alpha-ol-17-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5beta-androstan-3beta,17beta-diol + NADP+
?
-
Substrates: -
Products: -
?
5beta-androstan-3beta-ol-17-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5beta-dihydrocortisol + NADH
? + NAD+
-
Substrates: -
Products: -
r
5beta-pregnan-20alpha-ol-3-one + NAD(P)+
5beta-pregnan-3,20-dione + NAD(P)H
-
Substrates: -
Products: -
r
5beta-pregnan-20alpha-ol-3-one + NADP+
?
5beta-pregnan-3,20-dione + NADPH + H+
5alpha-pregnan-20alpha-ol-3-one + NADP+
-
Substrates: -
Products: -
r
5beta-pregnan-3alpha,20alpha-diol + NADP+
?
-
Substrates: -
Products: -
?
5beta-pregnan-3alpha,21-diol-20-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnan-3alpha,20alpha-diol + NAD(P)+
-
Substrates: -
Products: -
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
-
Substrates: -
Products: -
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
Substrates: -
Products: -
?
5beta-pregnan-3alpha-ol-20-one + NADPH + H+
?
-
Substrates: -
Products: -
?
5beta-pregnane-3,20-dione + NAD(P)H + H+
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
Substrates: -
Products: -
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
6-tert-butyl-2,3-epoxy-5-cyclohexen-1,4-dione + NADPH + H+
?
-
Substrates: -
Products: -
?
7alpha-hydroxy-dehydroepiandrosterone + NADPH + H+
?
-
Substrates: -
Products: -
?
9,10-phenanthrenequinone + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
acetoacetyl-CoA + NADPH
NADP+ + ?
acrolein + NADPH + H+
?
-
Substrates: -
Products: -
?
all-trans-retinal + NADPH + H+
?
-
Substrates: -
Products: -
?
alpha-tetralone + NADPH + H+
?
-
Substrates: -
Products: -
?
befunolol + NADPH + H+
?
-
Substrates: -
Products: -
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
-
Substrates: -
Products: -
?
benzene dihydrodiol + NADP+
2-hydroxycyclohexa-3,5-diene-1-one + NADPH + H+
-
Substrates: -
Products: -
r
benzyl acetoacetate + NADPH + H+
?
beta-ionol + NADP+
?
-
Substrates: -
Products: -
?
camphorquinone + NADP+
?
-
Substrates: -
Products: -
r
cis-benzene-1,2-dihydrodiol + NADP+
?
corticosterone + NADH + H+
? + NAD+
corticosterone + NADPH + H+
? + NADP+
-
Substrates: less reactive than with 17alpha-hydroxyprogesterone
Products: -
?
cortisol + NADH
20alpha-dihydrocortisol + NAD+
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
cortisone + NADH
? + NAD+
D-galactose + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
D-glucose + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
D-glyceraldehyde + NADPH + H+
glycerol + NADP+
D-lactaldehyde + NADPH + H+
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
dehydroepiandrosterone + NADPH + H+
?
-
Substrates: -
Products: -
?
dehydroepiandrosterone 3-sulfate + NADPH + H+
?
-
Substrates: -
Products: -
?
diacetyl + NADPH + H+
?
-
Substrates: -
Products: -
?
dihydrotestosterone + NADPH
? + NADP+
-
Substrates: -
Products: -
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
DL-glyceraldehyde + NADPH
glycerol + NADP+
-
Substrates: -
Products: -
?
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
dydrogesterone + NADH + H+
20alpha-hydroxydydrogesterone + NAD+
-
Substrates: -
Products: -
?
estrone + NADPH + H+
?
-
Substrates: -
Products: -
?
estrone 3-sulfate + NADPH + H+
?
-
Substrates: -
Products: -
?
ethyl 2-methylacetoacetate + NADPH
NADP+ + ?
ethyl 3-oxovalerate + NADPH + H+
?
ethyl 4-chloroacetoacetate + NADPH
NADP+ + ?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
ethyl benzoylacetate + NADPH + H+
?
ethyl pyruvate + NADPH
NADP+ + ?
geraniol + NADP+
?
-
Substrates: -
Products: -
?
hexanal + NADPH + H+
?
-
Substrates: -
Products: -
?
isatin + NADP+
?
-
Substrates: -
Products: -
?
isocaproaldehyde + NADPH + H+
?
-
Substrates: -
Products: -
?
ketotifen + NADPH + H+
?
-
Substrates: -
Products: -
?
menadione + NADPH + H+
?
-
Substrates: -
Products: -
?
methyl acetoacetate + NADPH + H+
?
methylglyoxal + NADPH
NADP+ + ?
methylglyoxal + NADPH + H+
?
-
Substrates: -
Products: -
?
n-butyl acetoacetate + NADPH + H+
?
n-hexyl acetoacetate + NADPH + H+
?
n-octyl acetoacetate + NADPH + H+
?
nonanal + NADPH + H+
?
-
Substrates: -
Products: -
?
phenylglyoxal + NADPH + H+
?
-
Substrates: -
Products: -
r
progesterone + NAD(P)+
20alpha-hydroxyprogesterone + NAD(P)H + H+
Substrates: -
Products: -
?
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
progesterone + NADH
20alpha-hydroxyprogesterone + NAD+
-
Substrates: -
Products: -
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
prostaglandin E2 + NADPH
NADP+ + ?
-
Substrates: low activity
Products: -
?
pyridine 3-aldehyde + NADPH + H+
?
-
Substrates: -
Products: -
?
pyridine-3-aldehyde + NADPH
NADP+ + ?
pyridine-4-aldehyde + NADP+
?
testosterone + NADP+
?
-
Substrates: -
Products: -
?
tetrahydrocortisol + NADH + H+
? + NAD+
trans-1S,2S-cyclohexanediol + NADP+
?
trans-2-hexenal + NADPH + H+
?
-
Substrates: -
Products: -
?
trans-2-nonenal + NADPH + H+
?
-
Substrates: -
Products: -
?
trans-benzene dihydrodiol + NADP+
?
-
Substrates: -
Products: -
?
trans-benzene-1S,2S-dihydrodiol + NADP+
?
additional information
?
-
(S)-methyl 3-hydroxybutyrate + NADP+

methyl acetoacetate + NADPH + H+
-
Substrates: -
Products: -
r
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
-
Substrates: -
Products: -
r
1,2-cyclohexanedione + NADP+

?
-
Substrates: 66% activity compared to pyridine 3-aldehyde
Products: -
r
1,2-cyclohexanedione + NADP+
?
-
Substrates: 50% activity compared to pyridine 3-aldehyde
Products: -
r
1-phenyl-1,2-propanedione + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
1-phenyl-1,2-propanedione + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
11-deoxycorticosterone + NAD(P)H

4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
Substrates: -
Products: -
?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
Substrates: -
Products: -
?
11-deoxycortisol + NADH

? + NAD+
-
Substrates: -
Products: -
?
11-deoxycortisol + NADH
? + NAD+
-
Substrates: -
Products: -
?
11-deoxycortisol + NADH
? + NAD+
-
Substrates: inducer
Products: -
r
11-deoxycortisol + NADH + H+

? + NAD+
Substrates: i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
Products: -
?
11-deoxycortisol + NADH + H+
? + NAD+
Substrates: i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
Products: -
?
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+

17alpha-hydroxyprogesterone + NAD(P)H
-
Substrates: inactive molecule form
Products: hormone
r
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
-
Substrates: -
Products: -
r
17alpha-hydroxypregnenolone + NADPH

? + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxypregnenolone + NADPH
? + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NAD(P)H

17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
Substrates: the aldo-keto reductase, AKR1C23, also shows 20alpha-hydroxysteroid dehydrogenase activity in vivo, enzyme regulation in preovulatory follicles and corpora lutea, overview
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: the enzyme activity is highest in women with visceral obesity
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: progesterone catabolism
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: regulation of enzyme expression during pregnancy, the enzyme is required for prostaglandin F2alpha-dependent progesterone down-regulation before parturition, overview
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: NADPH is preferred to NADH in liver, while the kidney enzyme is specific for NADPH
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: progesterone catabolism
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H + H+

17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
Substrates: NADPH preferred
Products: -
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
Substrates: NADPH preferred
Products: -
?
17alpha-hydroxyprogesterone + NADPH

17alpha,20alpha-dihydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NADPH + H+

17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
Substrates: -
Products: -
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
Substrates: best substrate
Products: -
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
Substrates: -
Products: -
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
Substrates: -
Products: -
r
2,3-butanediol + NADP+

?
-
Substrates: -
Products: -
r
2,3-butanediol + NADP+
?
-
Substrates: -
Products: -
r
2,3-butanedione + NADPH

? + NADP+
-
Substrates: -
Products: -
?
2,3-butanedione + NADPH
? + NADP+
-
Substrates: -
Products: -
?
2,3-heptanedione + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
2,3-heptanedione + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
2,3-hexanedione + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
2,3-hexanedione + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
2,3-pentanedione + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
2,3-pentanedione + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
2,4-pentanedione + NADP+

?
-
Substrates: -
Products: -
r
2,4-pentanedione + NADP+
?
-
Substrates: -
Products: -
r
20alpha-hydroxyprogesterone + NADP+

progesterone + NADPH
-
Substrates: -
Products: -
r
20alpha-hydroxyprogesterone + NADP+
progesterone + NADPH
-
Substrates: -
Products: -
?
3,4-hexanedione + NADP+

?
-
Substrates: -
Products: -
r
3,4-hexanedione + NADP+
?
-
Substrates: -
Products: -
r
4-nitrobenzaldehyde + NADPH

4-nitrobenzyl alcohol + NADP+
-
Substrates: -
Products: -
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
Substrates: -
Products: -
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
Substrates: -
Products: -
?
5alpha-dihydroprogesterone + NADPH + H+

5alpha,20alpha-tetrahydroprogesterone + NADP+
Substrates: -
Products: -
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
Substrates: -
Products: -
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
Substrates: -
Products: -
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+

3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
-
Substrates: -
Products: -
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
Substrates: -
Products: -
?
5beta-pregnan-20alpha-ol-3-one + NADP+

?
-
Substrates: -
Products: -
?
5beta-pregnan-20alpha-ol-3-one + NADP+
?
-
Substrates: -
Products: -
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+

5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
Substrates: -
Products: -
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
Substrates: -
Products: -
?
acetoacetyl-CoA + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
acetoacetyl-CoA + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
acetoin + NADPH + H+

?
-
Substrates: -
Products: -
?
acetoin + NADPH + H+
?
-
Substrates: -
Products: -
r
acetoin + NADPH + H+
?
-
Substrates: -
Products: -
r
benzyl acetoacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
benzyl acetoacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
cis-benzene-1,2-dihydrodiol + NADP+

?
-
Substrates: -
Products: -
r
cis-benzene-1,2-dihydrodiol + NADP+
?
-
Substrates: -
Products: -
r
corticosterone + NADH + H+

? + NAD+
Substrates: i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
Products: -
?
corticosterone + NADH + H+
? + NAD+
Substrates: i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
Products: -
?
cortisol + NADH

20alpha-dihydrocortisol + NAD+
-
Substrates: -
Products: -
r
cortisol + NADH
20alpha-dihydrocortisol + NAD+
-
Substrates: inducer
Products: -
r
cortisol + NADH + H+

20beta-hydroxycortisol + NAD+
Substrates: -
Products: -
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
Substrates: no activity with NADPH
Products: -
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
Substrates: -
Products: -
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
Substrates: no activity with NADPH
Products: -
?
cortisone + NADH

? + NAD+
-
Substrates: -
Products: -
?
cortisone + NADH
? + NAD+
-
Substrates: inducer
Products: -
r
D-glyceraldehyde + NADPH + H+

glycerol + NADP+
-
Substrates: -
Products: -
r
D-glyceraldehyde + NADPH + H+
glycerol + NADP+
-
Substrates: -
Products: -
r
D-lactaldehyde + NADPH + H+

?
-
Substrates: -
Products: -
r
D-lactaldehyde + NADPH + H+
?
-
Substrates: -
Products: -
r
daunorubicin + NADPH + H+

daunorubicinol + NADP+
Substrates: inactivation of the anticancer drug
Products: -
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
Substrates: the enzyme reduces daunorubicin to its corresponding alcohol daunorubicinol using NADPH as the coenzyme
Products: -
r
dihydrotestosterone + NADPH + H+

4-androsten-3alpha,17beta-diol + NADP+
Substrates: reaction of EC 1.1.1.357
Products: -
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
Substrates: reaction of EC 1.1.1.357
Products: -
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
-
Substrates: reaction of EC 1.1.1.357
Products: -
r
DL-glyceraldehyde 3-phosphate + NADPH + H+

glycerol 3-phosphate + NADP+
-
Substrates: -
Products: -
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
-
Substrates: -
Products: -
r
ethyl 2-methylacetoacetate + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
ethyl 2-methylacetoacetate + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
ethyl 3-oxovalerate + NADPH + H+

?
-
Substrates: -
Products: -
r
ethyl 3-oxovalerate + NADPH + H+
?
-
Substrates: -
Products: -
r
ethyl 4-chloroacetoacetate + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
ethyl 4-chloroacetoacetate + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
ethyl acetoaetate + NADPH

(S)-ethyl 3-hydroxybutyrate + NADP+
-
Substrates: -
Products: -
?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
-
Substrates: -
Products: -
r
ethyl benzoylacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
ethyl benzoylacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
ethyl pyruvate + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
ethyl pyruvate + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
isatin + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
isatin + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
methyl acetoacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
methyl acetoacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
methylglyoxal + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
methylglyoxal + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
methylglyoxal + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
n-butyl acetoacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
n-butyl acetoacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
n-hexyl acetoacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
n-hexyl acetoacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
n-octyl acetoacetate + NADPH + H+

?
-
Substrates: -
Products: -
r
n-octyl acetoacetate + NADPH + H+
?
-
Substrates: -
Products: -
r
phenylglyoxal + NADP+

?
-
Substrates: -
Products: -
r
phenylglyoxal + NADP+
?
-
Substrates: -
Products: -
r
progesterone + NAD(P)H

20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: -
Products: -
r
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
Substrates: i.e. pregn-4-en-3-one, importance of sulfhydryl groups in the functioning of the enzyme
Products: -
r
progesterone + NAD(P)H

20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: -
Products: -
r
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: NADPH much more efficient, 4-fold lower Km
Products: -
?
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: -
Products: -
?
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: -
Products: -
r
progesterone + NAD(P)H + H+

20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: -
Products: -
ir
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
-
Substrates: maternal and fetal 20alpha-HSD play a role in maintaining normal pregnancy at least partially by reducing progesterone concentrations in fetuses
Products: -
?
progesterone + NADH + H+

20alpha-hydroxyprogesterone + NAD+
Substrates: -
Products: -
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
-
Substrates: -
Products: -
?
progesterone + NADH + H+
20alpha-hydroxyprogesterone + NAD+
-
Substrates: -
Products: -
?
progesterone + NADPH

20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: central role in luteolysis and parturition
Products: -
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: -
Products: -
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
Substrates: less reactive than with 17alpha-hydroxyprogesterone
Products: -
?
pyridine-3-aldehyde + NADPH

NADP+ + ?
-
Substrates: -
Products: -
?
pyridine-3-aldehyde + NADPH
NADP+ + ?
-
Substrates: -
Products: -
?
pyridine-4-aldehyde + NADP+

?
-
Substrates: -
Products: -
r
pyridine-4-aldehyde + NADP+
?
-
Substrates: -
Products: -
r
tetrahydrocortisol + NADH + H+

? + NAD+
Substrates: i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
Products: -
?
tetrahydrocortisol + NADH + H+
? + NAD+
Substrates: i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
Products: -
?
trans-1S,2S-cyclohexanediol + NADP+

?
-
Substrates: -
Products: -
r
trans-1S,2S-cyclohexanediol + NADP+
?
-
Substrates: -
Products: -
r
trans-benzene-1S,2S-dihydrodiol + NADP+

?
-
Substrates: -
Products: -
r
trans-benzene-1S,2S-dihydrodiol + NADP+
?
-
Substrates: -
Products: -
r
additional information

?
-
-
Substrates: androstenedione and corticosterone not substrates
Products: -
?
additional information
?
-
-
Substrates: negligible activity with dehydroepiandrosterone, estrone estradiol, 4-androstenendione, testosterone and diydrotestosterone as substrates
Products: -
?
additional information
?
-
-
Substrates: pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
Products: -
?
additional information
?
-
-
Substrates: pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
Products: -
?
additional information
?
-
-
Substrates: no activity with 5beta-androstan-17beta-ol-3-one, 5beta-pregnan-20alpha-ol-3-one, testosterone and 20alpha-hydroxy progesterone
Products: -
?
additional information
?
-
-
Substrates: no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
Products: -
?
additional information
?
-
-
Substrates: high activity for neuroactive steroids, 9,10-phenanthrenequinone and 4-nitrobenzaldehyde, low activity for 17alpha hydroxypregnenolone, D,L-glyceraldehyde and prostaglandin E2, no activity for 20beta-hydroxy-pregn-4-en-3-one, andro-, testosterone, 17alpha-, 17beta-oestradiol, oestrone and 5alpha-dihydrotestosterone, other substrates: DL-glyceraldehyde, prostaglandin E2, D-glucose, prednisolone, D-galactose, prednisone, pregnenolone, 5alpha-pregnane-3,20-dione, 9,10-phenanthrenequinone
Products: -
?
additional information
?
-
-
Substrates: no activity with 20beta isomer of 20alpha-hydroxyprogesterone, rising activity with 20alpha-hydroxyprogesterone concentrations over the range 0.05-1.0 mM, increasing activity with NADP+ over the range 0.01-0.2 mM, no NAD+ activity over this concentration range
Products: -
?
additional information
?
-
-
Substrates: no activity with 20beta-hydroxypregn-4-en-3-one, 5alpha-pregnan-3,20-dione, 3beta-hydroxy-5alpha-pregnan-20-one and 3alpha,20alpha-dihydroxy-5alpha-pregnane
Products: -
?
additional information
?
-
-
Substrates: no activity with 20alpha-hydroxy-4-pregnen-3-one
Products: -
?
additional information
?
-
-
Substrates: benzaldehyde, DL-glyceraldehyde, 4-nitrobenzaldehyde and glucose very efficient substrates, methylglyoxal, 9,10-phenanthrenquinone and D-galactose less active, no activity with corticosterone and 5alpha-dihydrotestosterone
Products: -
?
additional information
?
-
-
Substrates: no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
Products: -
?
additional information
?
-
-
Substrates: no activity toward estrone with NADPH
Products: -
?
additional information
?
-
-
Substrates: less or no activity with 5beta-androstane-3,17-dione, 17beta-hydroxy-5beta-androstan-3-one, progesterone, 5beta-pregnane-3,20-dione, cortisone oestrone, 20-oxopregnenes without 17alpha-hydroxy group, 20-oxopregnanes, corticosteroides, 3- or 17-oxosteroids, 20beta-hydroxysteroids, 3- or 17-hydroxysteroids, alcohols as substrate, other substrates: isatin, ethyl acetoacetate, camphorquinone, pyridine-3-aldehyde, 1,2-cyclohexanedione, 2,4-pentanedione, 4-nitrobenzaldehyde, benzene-dihydrodiol
Products: -
?
additional information
?
-
-
Substrates: other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
Products: -
?
additional information
?
-
-
Substrates: role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
Products: -
?
additional information
?
-
-
Substrates: role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
Products: -
?
additional information
?
-
-
Substrates: other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
Products: -
?
additional information
?
-
-
Substrates: role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
Products: -
?
additional information
?
-
-
Substrates: 17alpha-hydroxyprogesterone inducer but not substrate
Products: -
?
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1,10-phenanthroline
-
50% inhibition at 0.065 mM
1,2-naphthoquinone
-
0.01 mM, 55% inhibition of enzyme in liver, 10% in kidney, 10% in lung cytosolic fraction, respectively
1-phenylcyclopentanecarboxylic acid
-
16alpha-Bromoacetoxyprogesterone
-
-
17alpha-hydroxyprogesterone
-
most inhibitory at pH 8.0, significant at pH 6.8
17beta-estradiol
-
20alpha-hydroxyprogesterone analog, competitive or noncompetitive depending on variable substrate
2',5'-adenosine bisphosphate
-
competitive inhibition versus NADP+
2',5'-ADP
-
coenzyme-competitive inhibitor
2'-adenylic acid
-
coenzyme-competitive inhibitor
2'-phosphoadenosine diphosphoribose
2,4-Pentanedione
-
pH profile for the inactivation, overview
2-(4-chlorobenzylidene)cyclopentanone
-
2-(4-chlorobenzylidene)cyclopentyl ethyl ether
-
2-acetylbenzofuran
-
50% inhibition at 0.033 mM
20beta-hydroxypregn-4-en-3-one
-
marginally inhibitory at pH 8.0
3',3'',5',5''-tetrabromophenolphthalein
3',3'',5',5''-tetrabromophenolphthalein diacetate
-
50% inhibition at 350 nM
3',3'',5',5''-tetraiodophenolphthalein
-
50% inhibition at 120 nM
3',5'-cyclic AMP
-
coenzyme-competitive inhibitor
3,5-dibromo-4-hydroxybenzoic acid methyl ester
-
50% inhibition at 0.099 mM
3,5-dibromosalicylic acid
-
-
3,5-dichlorosalicylic acid
3,5-diiodosalicylic acid
-
competitive
3-Aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
3-bromo-5-phenylsalicylic acid
3-chloro-5-phenylsalicylic acid
3-phenyl-5-bromosalicylic acid
-
-
3-phenylcyclopentanecarboxylic acid
-
4'-butyl-5-chloro-4-hydroxybiphenyl-3-carboxylic acid
7fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5'-adenosine diphosphate
-
-
5'-Adenosine triphosphate
-
-
5'-adenylic acid
-
coenzyme-competitive inhibitor
5'-ADP
-
coenzyme-competitive inhibitor
5'-ATP
-
coenzyme-competitive inhibitor
5-chloro-4-hydroxy-3'-methylbiphenyl-3-carboxylic acid
13fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxy-4'-methylbiphenyl-3-carboxylic acid
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-chloro-4-hydroxybiphenyl-3-carboxylic acid
24fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5-fluoro-4-hydroxybiphenyl-3-carboxylic acid
1.2fold selectivity relative to 3alpha-hydroxysteroid dehydrogenase AKR1C2
5alpha-dihydrotestosterone
-
-
5beta-dihydrotestosterone
-
-
9,10-phenanthrenequinone
-
0.01 mM, 70% inhibition of enzyme in liver, 5% in kidney, 60% in lung cytosolic fraction, respectively
adenosine 2'-monophospho- 5'-diphosphoribose
-
strong inhibition
adenosine diphosphoribose
-
coenzyme-competitive inhibitor
aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
-
aminopyridine adenine dinucleotide phosphate
-
-
androstendione
-
most inhibitory at pH 8.0
benzbromarone acetate
-
50% inhibition at 430 nM
benzofuran
-
50% inhibition at 1.45 mM
benzofuran-2-carboxylic acid
-
50% inhibition at 0.16 mM
Bethamethasone
-
0.1 mM, 10% inhibition
carboxylic acid
-
competitive for acetic and propionic acid, mixed-type from pentanoic to undecanoic acid with exception of heptanoic acid
cloxazolam
-
0.01 mM, 38% inhibition
diazepam
-
50% inhibition at 0.0056 mM
Diazotized 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate
-
NADP+ analog, competitive inhibitor
Diazotized 3-aminopyridine adenine dinucleotide phosphate
-
NADP analog, competitive inhibitor
dibenzofuran
-
50% inhibition at 0.895 mM
Diphenic acid
-
less than 17% inhibition
Fluorescein mercuric acetate
-
-
glycerol
-
inhibition partially reversed by cysteine
glycyrrhetinic acid
-
50% inhibition at 0.0022 mM
linear monocarboxylic acids
-
slight inhibition, overview
-
linear N-alkylammonium chloride derivatives
-
slight inhibition, overview
-
lithocholic acid
-
50% inhibition at 0.022 mM
Maleimide
-
pH profile for the inactivation, overview
Meclofenamic acid
-
20alpha-hydroxyprogesterone oxidation
medazepam
-
50% inhibition at 0.0047 mM
Medroxyprogesterone acetate
-
50% inhibition at 700 nM
N-1-butylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-decylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-dodecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-ethylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-heptylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-hexylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-methylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-nonylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-octylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-1-pentylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-propylnicotinamide chloride
-
inhibition of the ovarian enzyme, competitive inhibition versus NADP+
N-1-undecylnicotinamide chloride
-
inhibition of the ovarian enzyme, mixed type inhibition versus NADP+
N-alkylammonium chloride
-
competitive from pentyl to heptyl, mixed type from nonyl to dodecyl
N-Alkylmaleimide
-
N-ethylmaleimide and N-butylmaleimide to N-octylmaleimide at 25°C, pH 7.7
N-alkylmaleimides
-
coenzyme-competitive inhibition, varying in chainlength from N-ethyl- to N-octylmaleimide, effectively inactivated the enzyme through pseudo-first-order rate processes, overview
-
N-Butylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-ethylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Heptylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Hexylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Octylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N-Pentylmaleimide
-
inactivation via sulfhydryl groups of the enzyme in a nonpolar region
N1-alkylnicotinamide chloride
-
competitive from methyl to heptyl, mixed-type from octyl to dodecyl with respect to NADP
NAD+
-
NADP analog, competitive inhibitor
NADH
-
concentrations above 0.1 mM
NADPH
-
competitive and noncompetitive product inhibition with respect to NADP+ depending on substrate concentrations
natural oestrogens
-
e.g. oestrone less than 15% inhibition
-
o-cresolphthalein
-
50% inhibition at 140 nM
p-chloromercuribenzoate
-
also other sufhydryl reagents like 5,5'-dithiobis-2-nitrobenzoic acid and iodoacetamide strong
phenazine methosulfate
-
0.01-0.3 mg/ml
prolactin
-
down-regulating of gene-expression
-
pyridoxal 5'-phosphate
-
strong, 90% inactivation by 10 mM
synthetic non-steroidal oestrogens
-
hexoestrol most potent competitive inhibitor
-
synthetic oestrogens
-
e.g. hexestrol, silbestrol, dienstrol
-
Ursodeoxycholic acid
-
50% inhibition at 0.34 mM
valporic acid
-
less than 17% inhibition
2'-phosphoadenosine diphosphoribose

-
coenzyme-competitive inhibitor
2'-phosphoadenosine diphosphoribose
-
NADP+ analog, competitive or noncompetitive depending on variable substrate
3',3'',5',5''-tetrabromophenolphthalein

-
50% inhibition at 33 nM
3',3'',5',5''-tetrabromophenolphthalein
-
-
3,5-dichlorosalicylic acid

potent inhibitor
3,5-dichlorosalicylic acid
-
3,5-dichlorosalicylic acid
-
-
3-Aminopyridine adenine dinucleotide phosphate

-
NADP analog, competitive inhibitor
3-Aminopyridine adenine dinucleotide phosphate
-
diazotized, coenzyme-competitive at 25°C, pH 7.4, reversible binding
3-Aminopyridine adenine dinucleotide phosphate
-
-
3-bromo-5-phenylsalicylic acid

-
-
3-bromo-5-phenylsalicylic acid
-
3-chloro-5-phenylsalicylic acid

-
3-chloro-5-phenylsalicylic acid
-
-
apigenin

-
high inhibition
apigenin
-
0.02 mM, 90% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 45% inhibition in kidney cytosolic fraction
apigenin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
benzbromarone

-
50% inhibition at 48 nM
Bile acids

-
e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bile acids
-
e.g. lithocholic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
Bromophenol blue

-
50% inhibition at 0.011 mM
Bromophenol blue
-
little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, moderate inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
cibacron

-
coenzyme analog, competitively with respect to both coenzymes
cibacron
-
coenzyme analog, competitively with respect to both coenzymes
Cu2+

-
very powerful
Dienstrol

-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Dienstrol
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
ethyl acetate

-
noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
ethyl acetate
-
noncompetitively with respect to NADP+ and (S)-ethyl 3-hydroxybutyrate at backward reaction
fatty acids

-
e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fatty acids
-
e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
fisetin

-
high inhibition
fisetin
-
0.02 mM, 95% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
fisetin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
Flufenamic acid

-
50% inhibition at 0.0053 mM
Flufenamic acid
-
poor inhibition for 20alpha-hydroxyprogesterone oxidation
Hexestrol

-
50% inhibition at 0.0083 mM
indomethacin

-
50% inhibition at 0.13 mM
indomethacin
-
less than 17% inhibition
kaempferol

-
high inhibition
kaempferol
-
0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 15% inhibition in kidney cytosolic fraction
kaempferol
-
potent and competitive inhibitor
luteolin

-
high inhibition
luteolin
-
0.02 mM, 80% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 40% inhibition in kidney cytosolic fraction
myricetin

-
0.02 mM, 60% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 10% inhibition in kidney cytosolic fraction
NADP+

-
coenzyme-competitive inhibitor
NADP+
-
(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
NADP+
-
(non)competitively with respect to NADPH and ethyl acetoacetate at forward reaction
naringenin

-
high inhibition
naringenin
-
0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 3% inhibition in kidney cytosolic fraction
naringenin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
Phenobarbital

-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Phenobarbital
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Phenolphthalein

-
50% inhibition at 340 nM
progesterone

-
noncompetitive product inhibition
progesterone
-
1.5 mM marginally inhibitory at pH 8.0, 0.75-1.5 mM reduces activity at pH 6.8 by 46 and 60%, respectively; most inhibitory at pH 8.0, significant at pH 6.8
quercetin

-
high inhibition
quercetin
-
0.02 mM, 85% inhibition of enzyme in liver cytosolic fraction, 0.05 mM, 20% inhibition in kidney cytosolic fraction
quercetin
-
inhibitory effect on hepatic NADPH-dependent activity in decreasing order: fisetin > apigenin > naringenin > quercetin
quercetin
-
potent and competitive inhibitor
quercitrin

-
-
quercitrin
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
quercitrin
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
sorbinil

-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
sorbinil
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Sulfobromophthalein

-
little effect on hepatic NADPH-dependent 20alpha-hydroxysteroid dehydrogenase, potent inhibitor of hepatic NADH-dependent 20alpha-hydroxysteroid dehydrogenase activity
Tolrestat

-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
Tolrestat
-
competitive with respect to (S)-ethyl 3-hydroxybutyrate
additional information

-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups
-
additional information
-
adenosine: no inhibition, important features of coenzyme structure binding to coenzyme-binding site are 2'-phosphate, diphosphate and the positively charged ring nitrogen, hydrophobic region nearby the NADP-binding site might be responsible for nonpolar faciliation of the rates of maleimide inactivation; no inhibition by ATP, 3,5-cyclic AMP, and by adenosine up to 7.5 mM
-
additional information
-
NADP+, 3-aminopyridine adenine dinucleotide phosphate and three adenosine derivatives protect enzyme against inactivation by N-ethylmaleimide, 20alpha-hydroxyprogesterone does not and N1-ethylnicotinamide chloride not significantly; apparent second-order rate constants for inactivation are observed to increase with increasing chain length of the N-alkylmaleimide used, NADP-and coenzyme-competitive inhibitors such as 3-aminopyridine adenine dinucleotide phosphate and various adenosine derivatives protect the enzyme against maleimide inactivation, whereas no protection is observed with the steroid substrate, overview; sulfhydryl groups are modified during inactivation
-
additional information
-
no inhibition by NADPH with saturating concentration of NADP+
-
additional information
-
not inhibited by indomethacin, tolmetin and steroidal anti-inflammatory drugs
-
additional information
-
no inhibition but increase at preincubation with antiserum
-
additional information
-
Ca2+, Fe2+, Mg2+, Mn2+, Cd2+ and Zn2+ no significant effect
-
additional information
-
no inhibition with thiol reagents, reducing or chelating agents, ADH inhibitors
-
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-
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Inhibitory effects of diesel exhaust components and flavonoids on 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues
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Several distinct enzymes catalyze 20alpha-hydroxysteroid dehydrogenase activity in mouse liver and kidney
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2007
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Dhagat, U.; Carbone, V.; Chung, R.P.; Matsunaga, T.; Endo, S.; Hara, A.; El-Kabbani, O.
A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase
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2007
Homo sapiens
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Dhagat, U.; Endo, S.; Sumii, R.; Hara, A.; El-Kabbani, O.
Selectivity determinants of inhibitor binding to human 20alpha-hydroxysteroid dehydrogenase: crystal structure of the enzyme in ternary complex with coenzyme and the potent inhibitor 3,5-dichlorosalicylic acid
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51
4844-4848
2008
Homo sapiens (Q04828), Homo sapiens
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El-Kabbani, O.; Scammells, P.J.; Gosling, J.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)
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52
3259-3264
2009
Homo sapiens
brenda
Choi, J.H.; Ishida, M.; Matsuwaki, T.; Yamanouchi, K.; Nishihara, M.
Involvement of 20alpha-hydroxysteroid dehydrogenase in the maintenance of pregnancy in mice
J. Reprod. Dev.
54
408-412
2008
Mus musculus
brenda
Smuc, T.; Rizner, T.L.
Aberrant pre-receptor regulation of estrogen and progesterone action in endometrial cancer
Mol. Cell. Endocrinol.
301
74-82
2009
Homo sapiens
brenda
Dhagat, U.; Endo, S.; Soda, M.; Hara, A.; El-Kabbani, O.
Factorizing the role of a critical leucine residue in the binding of substrate to human 20alpha-hydroxysteroid dehydrogenase (AKR1C1): molecular modeling and kinetic studies of the Leu308Val mutant enzyme
Bioorg. Med. Chem. Lett.
20
5274-5276
2010
Homo sapiens (Q04828), Homo sapiens
brenda
Stefane, B.; Brozic, P.; Vehovc, M.; Rizner, T.L.; Gobec, S.
New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3
Eur. J. Med. Chem.
44
2563-2571
2009
Homo sapiens (Q04828)
brenda
El-Kabbani, O.; Scammells, P.J.; Day, T.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-based optimization and biological evaluation of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) salicylic acid-based inhibitors
Eur. J. Med. Chem.
45
5309-5317
2010
Homo sapiens (Q04828), Homo sapiens
brenda
Naumann, J.M.; Zoellner, A.; Dragan, C.A.; Messinger, J.; Adam, J.; Bureik, M.
Biotechnological production of 20-alpha-dihydrodydrogesterone at pilot scale
Appl. Biochem. Biotechnol.
165
190-203
2011
Homo sapiens
brenda
El-Kabbani, O.; Dhagat, U.; Soda, M.; Endo, S.; Matsunaga, T.; Hara, A.
Probing the inhibitor selectivity pocket of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) with X-ray crystallography and site-directed mutagenesis
Bioorg. Med. Chem. Lett.
21
2564-2567
2011
Homo sapiens
brenda
Naumann, J.M.; Messinger, J.; Bureik, M.
Human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)-dependent biotransformation with recombinant fission yeast Schizosaccharomyces pombe
J. Biotechnol.
150
161-170
2010
Homo sapiens
brenda
Nanjidsuren, T.; Naidansuren, P.; Park, C.W.; Park, J.J.; Yun, S.J.; Sim, B.W.; Kang, M.H.; Lee, S.R.; Chang, K.T.; Min, K.S.
Expression and localization of the 20alpha-hydroxysteroid dehydrogenase (HSD) enzyme in the reproductive tissues of the cynomolgus monkey Macaca fascicularis
J. Steroid Biochem. Mol. Biol.
127
337-344
2011
Macaca fascicularis
brenda
Naidansuren, P.; Park, C.W.; Kim, S.H.; Nanjidsuren, T.; Park, J.J.; Yun, S.J.; Sim, B.W.; Hwang, S.; Kang, M.H.; Ryu, B.Y.; Hwang, S.Y.; Yoon, J.T.; Yamanouchi, K.; Min, K.S.
Molecular characterization of bovine placental and ovarian 20alpha-hydroxysteroid dehydrogenase
Reproduction
142
723-731
2011
Bos taurus
brenda
Kim, S.; Shin, Y.; Kang, M.; Yoon, J.; Min, K.
Gene expression and localization of 20alpha-hydroxysteroid dehydrogenase (HSD) in reproductive tissues during early pregnancy of cattle
Anim. Reprod. Sci.
147
1-9
2014
Bos taurus, Bos taurus (D0VDT4)
brenda
Papp, E.; Balogun, K.; Banko, N.; Mohammadi, H.; Loutfy, M.; Yudin, M.; Shah, R.; Macgillivray, J.; Murphy, K.; Walmsley, S.; Silverman, M.; Serghides, L.
Low prolactin and high 20-alpha-hydroxysteroid dehydrogenase levels contribute to lower progesterone levels in hiv-infected pregnant women exposed to protease inhibitor-based combination antiretroviral therapy
J. Infect. Dis.
213
1532-1540
2016
Homo sapiens
brenda
Nanjidsuren, T.; Yun, S.J.; Park, C.W.; Kim, M.S.; Kang, M.H.; Min, K.S.
Expression and localization of 20alpha-hydroxysteroid dehydrogenase (20lpha-HSD) in porcine reproductive tissues during pregnancy
Anim. Reprod. Sci.
148
63-71
2014
Sus scrofa
brenda
Matsunaga, T.; Yamaguchi, A.; Morikawa, Y.; Kezuka, C.; Takazawa, H.; Endo, S.; El-Kabbani, O.; Tajima, K.; Ikari, A.; Hara, A.
Induction of aldo-keto reductases (AKR1C1 and AKR1C3) abolishes the efficacy of daunorubicin chemotherapy for leukemic U937 cells
Anticancer Drugs
25
868-877
2014
Homo sapiens (Q04828), Homo sapiens
brenda
Endo, S.; Arai, Y.; Hara, A.; Kitade, Y.; Bunai, Y.; El-Kabbani, O.; Matsunaga, T.
Substrate specificity and inhibitor sensitivity of rabbit 20alpha-hydroxysteroid dehydrogenase
Biol. Pharm. Bull.
36
1514-1518
2013
Oryctolagus cuniculus
brenda
Kwon, S.; Bang, W.; Jeong, J.; Cho, H.; Park, D.; Hwang, J.; Kim, T.; Ko, M.; Cho, I.; Joo, Y.; Jeong, M.; Kim, S.; Kim, C.
Important role of the C-terminal region of pig aldo-keto reductase family 1 member C1 in the NADPH-dependent reduction of steroid hormones
Indian J. Biochem. Biophys.
50
237-241
2013
Sus scrofa
brenda
Sudeshna, T.; Anand, K.; Medhamurthy, R.
Analysis of 20alpha-hydroxysteroid dehydrogenase expression in the corpus luteum of the buffalo cow: effect of prostaglandin F2-alpha treatment on circulating 20alpha-hydroxyprogesterone levels
Reprod. Biol. Endocrinol.
11
111
2013
Bos taurus
brenda
Rantala, M.H.; Mutikainen, M.; Schuler, G.; Katila, T.; Taponen, J.
Endometrial expression of progesterone, estrogen, and oxytocin receptors and of 20alpha-hydroxysteroid dehydrogenase and cyclooxygenase II 2 and 5 days after ovulation in induced short and normal estrous cycles in dairy cows
Theriogenology
81
1181-1188
2014
Bos taurus
brenda
Yoo, M.H.; Park, C.W.; Byambaragchaa, M.; Kang, M.H.; Min, K.S.
Data on the localization of EGFP and 20alpha-hydroxysteroid dehydrogenase (20alpha-HSD) in the placenta and testes of transgenic mice
Data Brief
19
632-637
2018
Mus musculus (Q8K023)
brenda
Giatti, S.; Diviccaro, S.; Falvo, E.; Garcia-Segura, L.; Melcangi, R.
Physiopathological role of the enzymatic complex 5alpha-reductase and 3alpha/beta-hydroxysteroid oxidoreductase in the generation of progesterone and testosterone neuroactive metabolites
Front. Neuroendocrinol.
57
100836
2020
Homo sapiens (Q04828), Mus musculus (Q91WT7), Rattus norvegicus
brenda
Doden, H.; Pollet, R.; Mythen, S.; Wawrzak, Z.; Devendran, S.; Cann, I.; Koropatkin, N.; Ridlon, J.
Structural and biochemical characterization of 20-hydroxysteroid dehydrogenase from Bifidobacterium adolescentis strain L2-32
J. Biol. Chem.
294
12040-12053
2019
Bifidobacterium adolescentis (A7A7R9), Bifidobacterium adolescentis L2-32 (A7A7R9)
brenda