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(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide + NAD+
?
-
-
-
-
r
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide + NADP+
?
(5beta,20R)-20-hydroxypregnan-3-one + NADH + H+
?
-
-
-
-
?
1-acenaphthenol + NADP+
?
-
isozymes AKR1C1-AKR1C4
-
-
r
1-acenaphthenol + NADPH
?
-
-
-
-
?
1-acetophenone + NADPH
1-phenylethanol + NADP+
-
-
-
-
?
1-indanol + NADP+
?
-
isozymes AKR1C1-AKR1C4
-
-
r
17beta-estradiol + NADP+
estrone + NADPH
-
-
-
-
r
17beta-hydroxy-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
-
-
-
r
2-decalol + NAD+
? + NADH + H+
-
-
-
?
3-hydroxysteroid + NAD(P)+
3-ketosteroid + NAD(P)H
-
-
-
?
3-oxocholic acid + NADPH
3alpha-hydroxycholic acid + NADP+
-
reverse reaction rate negligible
-
ir
3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine + NAD+
12alpha-hydroxy-3-oxo-5beta-cholanoyl glycine + NADH
-
-
-
-
?
3alpha,17alpha,21-trihydroxy-5beta-pregnan-11,20-dione + NADP+
17alpha,21-dihydroxy-5beta-pregnan-3,11,20-trione + NADPH
-
-
-
r
3alpha,17beta-androstene-3,17-diol + NAD(P)+
dihydrotestosterone + NAD(P)H + H+
-
-
-
?
3alpha,21-dihydroxy-5beta-pregnan-20-one + NADP+
21-hydroxy-5beta-pregnan-3,20-dione + NADPH
-
-
-
-
r
3alpha,5alpha,20alpha-trihydroxyprogesterone + NADP+
5alpha,20alpha-dihydroxyprogesterone-3-one + NADPH + H+
-
-
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl glycine + NADH
3alpha,7alpha-dihydroxy-5beta-cholanoyl glycine + NAD+
7alpha-hydroxy-3-oxo-5beta-cholanoyl glycine + NADH
-
-
-
-
?
3alpha-adiol + NAD(P)+
dihydrotestosterone + NAD(P)H
3alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH
-
oxidation utilizing NAD+ as a cofactor is the preferred reaction in vitro
-
-
r
3alpha-hydroxy-12-oxo-9,11-cholenic acid + NADP+
3,12-dioxo-9,11-cholenic acid + NADPH
-
-
-
-
?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH
-
-
-
-
?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH + H+
-
-
-
-
r
3alpha-hydroxy-5beta-androstan-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxypregn-4-en-20-one + NADP+
pregn-4-en-3,20-dione + NADPH + H+
-
-
-
-
?
3alpha-hydroxytibolone + NAD+
tibolone + NADH
isozymes AKR1C2 and AKR1C4, no activity with isozyme AKR1C1
-
-
r
3alpha-tetrahydroprogesterone + NADH
5alpha-dihydroprogesterone + NAD+
-
-
-
r
3beta-hydroxytibolone + NAD+
tibolone + NADH
isozymes AKR1C2, AKR1C1, and AKR1C4
-
-
r
4'-methoxyacetophenone + NADPH + H+
1-(4-methoxyphenyl)ethanol + NADP+
-
-
R,S-enantiomeric product
-
?
4-androsten-3alpha-ol-17-one + NADH + H+
4-androsten-3alpha,17beta-diol + NAD+
-
AKR1C17
-
-
r
4-androstene-3,17-dione + NADH + H+
4-androsten-3alpha-ol-17-one + NAD+
-
low activity
-
-
r
4-bromoacetophenone + NADPH + H+
1-(4-bromophenyl)ethanol + NADP+
-
-
-
-
?
4-cyanoacetophenone + NADPH + H+
1-(4-cyanophenyl)ethanol + NADP+
-
-
-
-
?
4-methylacetophenone + NADPH + H+
1-(4-methylphenyl)ethanol + NADP+
-
-
R,S-enantiomeric product
-
?
4-nitroacetophenone + NADPH + H+
1-(4-nitrophenyl)ethanol + NADP+
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
5alpha-androstan-3,17-dione + NADH + H+
androsterone + NAD+
-
-
-
?
5alpha-androstan-3,17-dione + NADPH + H+
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
5alpha-androstan-3alpha,17beta-diol + NAD(P)H
5alpha-dihydrotestosterone + NAD(P)+
5alpha-androstan-3alpha-ol-17-one + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
-
-
-
-
r
5alpha-androstane-3,17-dione + NADH
5alpha-androstan-3alpha-ol-17-one + NAD+
-
low activity
AKR1C9
-
r
5alpha-androstane-3,17-dione + NADH + H+
androsterone + NAD+
-
-
-
?
5alpha-dihydrocortisol + NADPH
3alpha,5alpha-tetrahydrocortisol + NADP+
-
-
-
?
5alpha-dihydroprogesterone + 2 NAD(P)H + 2 H+
pregnan-3alpha,20beta-diol + 2 NAD(P)+
-
-
-
-
?
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
5alpha-dihydroprogesterone + NADPH + H*
3alpha,5alpha-3-hydroxypregnan-20-one + 5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
(3alpha,5alpha)-3-hydroxypregnan-20-one + NADP+
-
isozymes AKR1C1-AKR1C4
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
5alpha-dihydroprogesterone + NADPH + H+
5alpha-hydroxy-pregnan-20-one + NADP+
-
isozyme AKR1C2
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
5alpha-dihydrotestosterone + NADH
3alpha-androstanediol + NAD+
-
reaction direction is regulated by the NAD+:NADPH relation in the cell
-
-
r
5alpha-dihydrotestosterone + NADH
?
-
low activity
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnane-20alpha-ol-3-one + NADH
5alpha-pregnane-3,20alpha-diol + NAD+
-
-
-
-
?
5alpha-pregnane-3,20-dione + NADH
5alpha-pregnan-3alpha-ol-20-one + NAD+
-
low activity
-
-
r
5beta-androstan-3,17-dione + NAD(P)H
5beta-androstan-17one-3-ol + NAD(P)+
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha,17alpha-diol + NADP+
-
-
-
r
5beta-androstan-3alpha,17beta-diol + NADP+
17beta-hydroxy-5beta-androstan-3-one + NADPH
5beta-androstan-3alpha-ol-17-one + NADH
5beta-androstane-3alpha,17beta-diol + NAD+
-
-
-
-
r
5beta-androstan-3alpha-ol-17-one + NADPH
5beta-androstan-3alpha,17alpha-diol + NADP+
-
-
-
r
5beta-androstane-3,17-dione + NADH
5beta-androstan-3alpha-ol-17-one + NAD+
-
-
-
-
r
5beta-androstane-3,17-dione + NADH + H+
5beta-androstan-3alpha-ol-17-one + NAD+
-
-
-
?
5beta-dihydrocortisol + NADPH
3alpha,5beta-tetrahydrocortisol + NADP+
-
-
-
?
5beta-dihydroprogesterone + NADPH
?
-
isozyme AKR1C1 and AKR1C2
-
-
?
5beta-dihydroprogesterone + NADPH + H+
3alpha,5beta-3-hydroxypregnan-20-one + NADP+
-
preferred substrate
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
5beta-pregnane-20alpha-ol-3-one + NADH + H+
5beta-pregnane-3,20alpha-diol + NAD+
-
-
-
-
?
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnan-3alpha-ol-20-one + NAD+
6-ketolithocholate + NAD+
5beta-cholan-3,6-dione-24-oic acid + NADH
-
-
-
-
r
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH
?
-
the enzyme produces both R- and S-form products in a ratio of 2.3 : 1
-
-
?
9,10-phenanthrenequinone + NADH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
androstenol + NAD+
? + NADH + H+
-
-
-
?
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
-
-
-
?
androsterone + NAD+
androstanedione + NADH
androsterone + NAD+
androstanedione + NADH + H+
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
-
r
androsterone + NADP+
androstane-3,17-dione + NADPH
benzenedihydrodiol + NADP+
?
-
isozymes AKR1C1-AKR1C4
-
-
r
benzoylpyridine + NADPH
?
-
-
-
-
?
beta-muricholic acid + NADH
?
-
low activity
-
-
?
chenodeoxycholic acid + NAD(P)+
7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
chenodeoxycholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
-
-
-
-
?
chenodeoxycholic acid + NADH
?
-
-
-
-
?
cholate + NAD+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NADH + H+
-
-
-
r
cholate + NAD+
7alpha,12alpha-dihydroxy-5-beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
cholic acid + NAD+
3-oxocholic acid + NADH + H+
-
-
-
-
r
cholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
-
-
-
-
?
cholic acid + NADH
?
-
low activity
-
-
?
cholic acid + NADPH + H+
?
-
-
-
-
r
cholic acid + thio-NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + thio-NADH
-
-
-
-
?
cyclohexanol + NAD+
? + NADH + H+
-
-
-
?
dehydrocholate + NADH + H+
?
-
-
-
?
dehydrolithocholic acid + NADH + H+
?
-
-
-
-
?
deoxycholic acid + NAD(P)+
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
deoxycholic acid + NADH
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD+
deoxycholic acid + NADH
?
-
low activity
-
-
?
diacetyl + NADH
?
-
-
-
-
?
dihydrotestosterone + NADPH
androstanediol + NADP+ + H+
-
-
-
?
estradiol + NAD(P)H
estrone + NAD(P)+
etiocholan-3alpha-ol-17-one + NADP+
etiocholan-3,17-dione + NADPH
-
-
-
-
?
fusidic acid + NAD+
3-oxofusidic acid + NADH
-
antibiotic steroid substrate
-
-
?
fusidic acid + NAD+
?
-
-
-
-
r
glycochenodeoxycholic acid + NADH
?
-
-
-
-
?
glycocholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl-glycine + NADH
-
-
-
-
?
glycolithocholic acid + NADH
?
-
-
-
-
?
glycolithocholic acid + NADP+
3-oxo-glycocholanoic acid + NADPH
glycoursodeoxycholic acid + NADH
?
-
-
-
-
?
hydroxybutyrate + NADP+
oxobutanoate + NADPH
-
-
-
-
?
hyodeoxycholic acid + NADH
?
-
low activity
-
-
?
isatin + NADH
?
-
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
-
-
-
-
?
lithocholic acid + NADH
?
-
-
-
-
?
lithocholic acid + NADP+
3-oxo-5beta-cholan-24-oic acid + NADPH
menadione + NADPH
?
-
-
-
-
?
metapyrone + NADH
?
-
-
-
-
?
murocholic acid + NADH
?
-
low activity
-
-
?
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)H
reduced 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)+
p-nitrobenzaldehyde + NAD(P)H
p-nitrobenzylalcohol + NAD(P)+
p-nitrobenzylalcohol + NAD+
p-nitrobenzaldehyde + NADH
-
-
-
r
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
progesterone + NADH
?
-
-
-
-
r
progesterone + NADPH
?
-
-
-
-
?
taurocholic acid + NAD(P)+
2[[7alpha,12alpha-dihydroxy-3,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADPH
taurocholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl-taurine + NADH
-
-
-
-
?
taurolithocholic acid + NADH
?
-
-
-
-
?
tauroursodeoxycholic acid + NADH
?
-
-
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
testosterone + NADH
?
-
low activity
-
-
?
testosterone + NADP+
4-androstene-3,17-dione + NADPH + H+
-
isozymes AKR1C1-AKR1C4
-
-
r
testosterone + NADPH + H+
4-androstene-3alpha,17beta-diol + NADP+
-
-
-
-
?
testosterone + NADPH + H+
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
tibolone + NADPH + H+
3alpha-hydroxytibolone + NADP+
isozyme AKR1C4 acts predominantly 3alpha-specific, isozyme AKR1C3 performs both 3alpha- and 3beta-reduction, tibolone is [7alpha,17alpha]-17-hydroxy-7-methyl-19-nor-pregn-5(10)-en-20-yn-3-one, or livial, a DELTA5(10)-ene-ketosteroid and a hormone replacement therapeutic used in the treatment of climacteric complaints and the prevention of osteoporosis, binding mode
-
-
r
tibolone + NADPH + H+
3beta-hydroxytibolone + NADP+
isozyme AKR1C1 is stereospecific forming exclusively the beta-isomer, isozyme AKR1C2 is 3beta-specific with substrate tibolone, isozyme AKR1C3 performs both 3alpha- and 3 beta-reduction, tibolbone is [7alpha,17alpha]-17-hydroxy-7-methyl-19-nor-pregn-5(10)-en-20-yn-3-one, or livial, a DELTA5(10)-ene-ketosteroid and a hormone replacement therapeutic used in the treatment of climacteric complaints and the prevention of osteoporosis
-
-
r
ursodeoxycholate + NAD+
7beta-hydroxy-3-oxo-5beta-cholan-24-oic acid + NADH
-
-
-
-
r
ursodeoxycholic acid + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oic acid + NADH
-
-
-
-
?
ursodeoxycholic acid + NADH
?
-
-
-
-
?
additional information
?
-
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide + NADP+
?
-
-
-
-
?
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide + NADP+
?
-
-
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP, the enzyme catalyzes the biosynthesis and oxidation of 3alpha,5alpha-reduced neurosteroids as allopregnanolone, which stimulates GABAA receptors, sciatic nerves-induced analgesia results in increased enzyme levels in neuropathic rats, overview
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP
-
-
r
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl glycine + NADH
-
-
-
-
?
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine + NAD+
7alpha,12alpha-dihydroxy-5beta-cholan-3-one-24-oyl glycine + NADH
-
-
-
-
?
3alpha-adiol + NAD(P)+
dihydrotestosterone + NAD(P)H
-
-
-
r
3alpha-adiol + NAD(P)+
dihydrotestosterone + NAD(P)H
-
-
-
r
3alpha-hydroxy-5beta-androstan-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
r
3alpha-hydroxy-5beta-androstan-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
-
r
3alpha-hydroxy-5beta-androstan-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
-
r
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
-
inhibition by Mg2+ only in oxidative direction
-
-
r
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
-
-
-
-
r
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
-
-
-
-
r
4-nitroacetophenone + NADPH + H+
1-(4-nitrophenyl)ethanol + NADP+
-
-
-
-
?
4-nitroacetophenone + NADPH + H+
1-(4-nitrophenyl)ethanol + NADP+
-
-
-
-
?
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
-
-
-
?, ir
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
-
-
-
-
ir
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
-
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
-
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
-
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD(P)H
5alpha-dihydrotestosterone + NAD(P)+
-
-
-
r
5alpha-androstan-3alpha,17beta-diol + NAD(P)H
5alpha-dihydrotestosterone + NAD(P)+
-
-
-
-
r
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
-
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
-
-
?
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
in the prostate: forward reaction by type 2 isozyme AKR1C3, reverse reaction by type 3 isozyme AKR1C2
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
inactivation of the potent androgen, 3alpha(beta)-hydroxysteroid oxidoreductase activity
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
isozyme AKR1C4
-
-
r
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
isozyme AKR1C2 acts 3alpha-specific on 5alpha-DHT, preferred substrate
-
-
r
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
preferred substrate for isozyme AKR1C4, while isozymes AKR1C1-3 show only low activity
-
-
r
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
isozyme AKR1C9
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
-
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
in the CNS: both reaction directions by type 3 isozyme AKR1C2
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
last step in neurosteroid allopregnanolone biosynthesis
-
-
?
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
type 2 isozyme AKR1C3 catalyzes the forward reaction, type 3 isozyme AKR1C2 catalyzes the reverse reaction
-
-
ir
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
type 3 isozyme AKR1C2
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
(3beta,5alpha,17beta)-androstane-3,17-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstan-3alpha,17beta-diol + NAD(P)+
-
i.e. 5alpha-androstan-17beta-ol-3-one
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
NADH-linked, particulate enzyme prefers oxidative reaction, while the NADPH-linked, cytosolic enzyme prefers the reductive reaction
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
i.e. DHT or 5alpha-androstane-17beta-ol-3-one, the reduction reaction is slightly preferred by the wild-type enzyme, which is determined by residue Arg276
i.e. 5alpha-androstane-3alpha,17beta-diol
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate, fluorometric activity measurement in intact cells, overview
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
i.e. DHT
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
i.e. DHT
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
-
-
-
?
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
-
-
-
?
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
-
-
-
r
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
?
5alpha-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
?
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, NADPH and NADH possible as cofactors
-
?
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
activity higher during lactation in female rats
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5beta-androstan-3,17-dione + NAD(P)H
5beta-androstan-17one-3-ol + NAD(P)+
-
-
-
-
r
5beta-androstan-3,17-dione + NAD(P)H
5beta-androstan-17one-3-ol + NAD(P)+
-
-
-
-
?
5beta-androstan-3,17-dione + NAD(P)H
5beta-androstan-17one-3-ol + NAD(P)+
-
-
-
-
r
5beta-androstan-3alpha,17beta-diol + NADP+
17beta-hydroxy-5beta-androstan-3-one + NADPH
-
-
-
-
r
5beta-androstan-3alpha,17beta-diol + NADP+
17beta-hydroxy-5beta-androstan-3-one + NADPH
-
-
-
-
r
5beta-androstan-3alpha,17beta-diol + NADP+
17beta-hydroxy-5beta-androstan-3-one + NADPH
-
-
-
-
r
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5beta-dihydrotestosterone + NAD(P)H
5beta-androstan-3alpha,17beta-diol + NAD(P)+
-
NADH-linked, particulate enzyme prefers oxidative reaction, while the NADPH-linked, cytosolic enzyme prefers the reductive reaction
-
r
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
r
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
r
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnan-3alpha-ol-20-one + NAD+
-
-
-
-
r
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnan-3alpha-ol-20-one + NAD+
-
-
-
-
r
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate, fluorometric activity measurement in intact cells, overview
-
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate
-
-
?
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
?
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD(P)+
5alpha-androstan-3,17-dione + NAD(P)H
-
i.e. 3alpha-hydroxy-5alpha-androstan-17-one
-
-
r
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
rate-limiting step in the reaction is the release of NADH
-
-
r
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
-
-
-
r
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
-
-
-
?
androsterone + NAD+
androstanedione + NADH
-
-
-
-
?
androsterone + NAD+
androstanedione + NADH
-
-
-
r
androsterone + NAD+
androstanedione + NADH
the intramolecular proton transfer is a rate-limiting step, with a concomitant releasing of protons to bulk solvent
-
-
r
androsterone + NAD+
androstanedione + NADH + H+
-
-
-
?
androsterone + NAD+
androstanedione + NADH + H+
the enzyme uses remote binding interactions to accelerate the reaction of androsterone with NAD+. The remote non-reacting sites of androsterone may induce a conformational change of the substrate binding loop with an entropic cost for better interaction with the transition state to decrease the enthalpy of activation, significantly increasing catalytic efficiency
-
-
?
androsterone + NAD+
androstanedione + NADH + H+
the rate limiting step is the release of NADH
-
-
?
androsterone + NAD+
androstanedione + NADH + H+
thermodynamic analysis of remote substrate binding energy. The remote non-reacting sites of androsterone may induce a conformational change of the substrate binding loop with an entropic cost for better interaction with the transition state to decrease the enthalpy of activation, significantly increasing catalytic efficiency
-
-
?
androsterone + NADP+
androstane-3,17-dione + NADPH
-
-
-
-
?
androsterone + NADP+
androstane-3,17-dione + NADPH
-
isozymes AKR1C2, and AKR1C4
-
-
r
camphorquinone + NADPH
?
-
-
-
-
?
camphorquinone + NADPH
?
-
-
-
-
?
chenodeoxycholic acid + NAD(P)+
7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
-
-
-
r
chenodeoxycholic acid + NAD(P)+
7alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
i.e. 3alpha,7alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
r
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
-
-
-
r
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
-
-
?
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
-
-
?
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
-
-
-
?
cholic acid + NAD(P)+
7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
-
-
-
-
?
deoxycholic acid + NAD(P)+
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NAD(P)+
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD(P)H + H+
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid
-
-
?
deoxycholic acid + NADH
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD+
-
-
-
r
deoxycholic acid + NADH
12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid + NAD+
-
-
-
r
estradiol + NAD(P)H
estrone + NAD(P)+
-
-
-
?
estradiol + NAD(P)H
estrone + NAD(P)+
-
-
-
?
glycolithocholic acid + NADP+
3-oxo-glycocholanoic acid + NADPH
-
i.e. 3alpha-hydroxy-5beta-cholanoyl glycine
-
-
?
glycolithocholic acid + NADP+
3-oxo-glycocholanoic acid + NADPH
-
i.e. 3alpha-hydroxy-5beta-cholanoyl glycine
-
-
?
lithocholic acid + NADP+
3-oxo-5beta-cholan-24-oic acid + NADPH
-
i.e. 3alpha-hydroxy-5beta-cholan-24-oic acid
-
-
?
lithocholic acid + NADP+
3-oxo-5beta-cholan-24-oic acid + NADPH
-
i.e. 3alpha-hydroxy-5beta-cholan-24-oic acid
-
-
?
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)H
reduced 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)+
-
synthetic compound with fluorophore core
-
-
r
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)H
reduced 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)+
-
synthetic compound with fluorophore core
-
-
r
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)H
reduced 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one + NAD(P)+
-
synthetic compound with fluorophore core
-
-
r
p-nitrobenzaldehyde + NAD(P)H
p-nitrobenzylalcohol + NAD(P)+
-
-
-
r
p-nitrobenzaldehyde + NAD(P)H
p-nitrobenzylalcohol + NAD(P)+
-
-
-
-
?
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
-
-
-
r
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
progesterone
allopregnanolone
-
r
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
progesterone
allopregnanolone
-
r
taurocholic acid + NAD(P)+
2[[7alpha,12alpha-dihydroxy-3,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADPH
-
-
-
-
?
taurocholic acid + NAD(P)+
2[[7alpha,12alpha-dihydroxy-3,24-dioxo-5beta-cholan-24-yl]amino]ethane sulfonic acid + NADPH
-
i.e. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl taurine
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
-
-
-
-
r
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
-
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
-
-
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
-
-
-
-
?
testosterone + NADPH + H+
?
-
-
-
-
?
testosterone + NADPH + H+
?
-
residues involved in substrate binding are T24, L54, F118, T226, W227, N306, and Y310
-
-
?
testosterone + NADPH + H+
?
-
substrate binding residues are T24, L54, Y55, H117, F118, F129, T226, W227, N306, and Y310
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
tibolone is used to treat climacteric symptoms and prevent osteoporosis, it exerts tissue-selective effects via site-specific metabolism into 3alpha- and 3beta-hydroxymetabolites and a DELTA4-isomer
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
i.e. [7alpha,17alpha]-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one, stereoselctive reaction to the 3alpha-hydroxytibolone product
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
i.e. [7alpha,17alpha]-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one, stereoselective reaction to the 3alpha-hydroxytibolone product
-
-
?
additional information
?
-
-
reduction of carbonyl compounds e.g. quinones, aliphatic-chain diketones, ketones
-
-
?
additional information
?
-
-
can not catalyze the dehydrogenation of 3beta-hydroxysteroids, epiandrosterone and 17beta-hydroxysteroids, i.e. testosterone and 17beta-estradiol
-
-
?
additional information
?
-
-
broad substrate range
-
-
?
additional information
?
-
-
bifunctional enzyme also catalyzing the reaction of carbonyl reductase, EC 1.1.1.184
-
-
?
additional information
?
-
the enzyme catalyzes reversibly the oxidoreduction of 3alpha-hydroxyl groups of steroid hormones
-
-
?
additional information
?
-
the enzyme catalyzes reversibly the oxidoreduction of 3alpha-hydroxyl groups of steroid hormones
-
-
?
additional information
?
-
-
a saturated 4,5 double bound is essential for enzyme activity, 3-ketosteroids are not used as substrates
-
-
?
additional information
?
-
-
can not catalyze conversion of 3alpha-androstanediol to 5alpha-dihydrotestosterone
-
-
?
additional information
?
-
-
structure-function relationship
-
-
?
additional information
?
-
-
type 3 isoform in liver virtually identical with bile acid-binding protein
-
-
?
additional information
?
-
due to inhibition by NADPH, the isozymes acts only as 3-ketosteroid reductases in vivo
-
-
?
additional information
?
-
-
due to inhibition by NADPH, the isozymes acts only as 3-ketosteroid reductases in vivo
-
-
?
additional information
?
-
-
enzyme inactivates steroid hormones in the liver, regulates 5alpha-dihydrotestosterone levels in the prostate, and forms the neurosteroid allopregnanolone in the CNS, isozymes might be involved in regulation of the levels of active androgens, estrogens, and progestrins
-
-
?
additional information
?
-
in vivo the isozymes act predominantly as 3-ketosteroid reductases due to inhibition by NADPH, but significantly produce 3beta-tetrahydrosteroids physiologically important in steroid metabolim, androgen metabolism, overview
-
-
?
additional information
?
-
-
in vivo the isozymes act predominantly as 3-ketosteroid reductases due to inhibition by NADPH, but significantly produce 3beta-tetrahydrosteroids physiologically important in steroid metabolim, androgen metabolism, overview
-
-
?
additional information
?
-
-
isozyme AKR1C2 is involved in neurosteroid biosynthesis, while isozyme AKE1C1 eliminates the neurosteroid precursor from the pathway and decreases the neurosteroid concentration in the brain, pathway overview
-
-
?
additional information
?
-
-
physiological roles of the isozymes AKR1C1-4, overview, enzyme regulates the occupancy and trans-activation of steroid hormone receptors by interconverting potent hormones with their cognate inactive metabolites
-
-
?
additional information
?
-
-
role of the isozymes in bile acid biosynthesis and steroid metabolism, product profiling, pre-receptor regulation of steroid hormone action, overview
-
-
?
additional information
?
-
-
isozymes AKR1C1, AKR1C4, and AKR1C2 show broad enzyme specificities, overview
-
-
?
additional information
?
-
-
isozymes display 3alpha-, 17beta-, and 20alpha-hydroxysteroid dehydrogenase activities to varying degrees, isozyme AKR1C4 shows the highest 3alpha-hydroxysteroid dehydrogenase activity of all isozymes, overview
-
-
?
additional information
?
-
molecular docking experiments using the crystal structures of isozymes AKR1C1 and AKR1C2 reveal the structural basis for stereospecificity of the isozymes
-
-
?
additional information
?
-
-
molecular docking experiments using the crystal structures of isozymes AKR1C1 and AKR1C2 reveal the structural basis for stereospecificity of the isozymes
-
-
?
additional information
?
-
stereospecificity differs between the isozymes, the enzyme also exhibits in vitro 3alpha[17beta]-hydroxysteroid axidase activity with 3alpha-diol as the substrate
-
-
?
additional information
?
-
-
stereospecificity differs between the isozymes, the enzyme also exhibits in vitro 3alpha[17beta]-hydroxysteroid axidase activity with 3alpha-diol as the substrate
-
-
?
additional information
?
-
-
structure-function study, the isozymes provide 3alpha-, 17beta-, and 20alpha-hydroxysteroid oxidase activity as well as 3-, 17-, and 20-ketosteroid reductase activity in vitro
-
-
?
additional information
?
-
-
AKR1C3 catalyzes androgen, estrogen, and prostaglandin metabolism, AKR1C3 is also involved in cancer development or progression
-
-
?
additional information
?
-
-
type I human hepatic 3alpha-hydroxysteroid dehydrogenase plays a significant role in bile acid biosynthesis, steroid hormone metabolism, and xenobiotic metabolism, the enzyme is regulated by expression level of the liver X receptor alpha, i.e. LXRalpha [NR1H3], a nuclear hormone receptor, predictive response element modeling and whole genome analysis of LXRalpha occupancy sites using ChIP/microarray technology, overview
-
-
?
additional information
?
-
-
AKR1C2 and AKR1C3 also possesse prostaglandin 9- and 11-reductase activities, EC 1.1.1.188 and EC 1.1.1.189, respectively, overview
-
-
?
additional information
?
-
-
reduction of carbonyl compounds e.g. quinones, aliphatic-chain diketones, ketones
-
-
?
additional information
?
-
-
absolutely specific for 3alpha-hydroxy group of C19, C21 and C24 steroids
-
-
?
additional information
?
-
-
acts faster on A/B cis hydroxysteroids than on A/B trans hydroxysteroids
-
-
?
additional information
?
-
-
absolutely specific for 3alpha-hydroxy group of C19, C21 and C24 steroids
-
-
?
additional information
?
-
-
belongs to the group of Y'bile acid binders, bile acid metabolizing enzymes
-
-
?
additional information
?
-
-
broad steroid substrate and cofactor specificity, no 3-oxosteroid reduction of testosterone
-
-
?
additional information
?
-
-
the enzyme catalyzes the reversible interconversion of hydroxyl and oxo groups at position 3 of the steroid nucleus
-
-
?
additional information
?
-
-
substrate specificity of various isozymes
-
-
?
additional information
?
-
-
belongs to the group of Y'bile acid binders, bile acid metabolizing enzymes
-
-
?
additional information
?
-
-
enzyme inactivates steroid hormones in the liver, regulates 5alpha-dihydrotestosterone levels in the prostate, and forms the neurosteroid allopregnanolone in the CNS
-
-
?
additional information
?
-
-
enzyme plays a pivotal role in the inactivation of circulating steroid hormones
-
-
?
additional information
?
-
-
enzyme regulates the occupancy and trans-activation of steroid hormone receptors by interconverting potent hormones with their cognate inactive metabolites
-
-
?
additional information
?
-
-
the high 3alpha-oxidoreductase activity in the hypothalamus of prepubertal rats is not related to the gonadal or adrenal steroids, the products are found in both prepubertal, mature, and castrated rats, rats with adrenalectomy show elevated enzyme activities, 3alpha-hydroxy progesterone is not related to the regulation of gonadotropin secretion in the male rat
-
-
?
additional information
?
-
-
enzyme acts positional and stereospecific, structure-function relationship
-
-
?
additional information
?
-
-
isozyme is positional- and stereospecific for the 3alpha-hydroxy steroid dehydrogenase reaction
-
-
?
additional information
?
-
-
wild-type enzyme recognizes only the 3-keto function of steroids, while the substrate binding residue-mutant enzymes show a broader substrate specificity and broader reaction spectra, overview, structure-function study on the basis of the crystal structure, modeling
-
-
?
additional information
?
-
-
AKR1C9 catalyzes androgen, estrogen, and prostaglandin metabolism
-
-
?
additional information
?
-
-
acetophenone derivatives are reduced enantioselectively by rat liver 3alpha-HSD to give (S)-alcohols
-
-
?
additional information
?
-
-
substrate specificty, overview, recombinant AKR1C17 efficiently oxidizes 3alpha-hydroxysteroids and diverse bile acids using NAD+ as the preferred coenzyme, no activity with progesterone, cortisone, and aldosterone. The enzyme also reduces non-steroidal alpha-dicarbonyl compounds such as 9,10-phenanethrenequinone, isatin, 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one and diacetyl, but does not show significant activities towards 4-nitrobenzaldehyde and 4-nitroacetophenone
-
-
?
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3-hydroxysteroid + NAD(P)+
3-ketosteroid + NAD(P)H
-
-
-
?
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP, the enzyme catalyzes the biosynthesis and oxidation of 3alpha,5alpha-reduced neurosteroids as allopregnanolone, which stimulates GABAA receptors, sciatic nerves-induced analgesia results in increased enzyme levels in neuropathic rats, overview
-
-
r
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH + H+
-
-
-
-
r
3alpha-hydroxypregn-4-en-20-one + NADP+
pregn-4-en-3,20-dione + NADPH + H+
-
-
-
-
?
4-pregnen-3alpha,20beta-diol + NAD+
(20beta)-20-hydroxypregn-4-en-3-one + NADH + H+
-
-
-
ir
5alpha-dihydroprogesterone + 2 NAD(P)H + 2 H+
pregnan-3alpha,20beta-diol + 2 NAD(P)+
-
-
-
-
?
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
5alpha-dihydrotestosterone + NADH
3alpha-androstanediol + NAD+
-
reaction direction is regulated by the NAD+:NADPH relation in the cell
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate, fluorometric activity measurement in intact cells, overview
-
-
?
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
androsterone + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
-
-
-
r
androsterone + NAD+
androstanedione + NADH
-
-
-
r
androsterone + NAD+
androstanedione + NADH + H+
-
-
-
?
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
-
r
dihydrotestosterone + NADPH
androstanediol + NADP+ + H+
-
-
-
?
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
tibolone is used to treat climacteric symptoms and prevent osteoporosis, it exerts tissue-selective effects via site-specific metabolism into 3alpha- and 3beta-hydroxymetabolites and a DELTA4-isomer
-
-
?
additional information
?
-
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
-
-
?
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
in the prostate: forward reaction by type 2 isozyme AKR1C3, reverse reaction by type 3 isozyme AKR1C2
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
inactivation of the potent androgen, 3alpha(beta)-hydroxysteroid oxidoreductase activity
-
-
ir
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
isozyme AKR1C4
-
-
r
5alpha-dihydroprogesterone + 2 NADPH + 2 H+
pregnan-3alpha,20beta-diol + 2 NADP+
-
isozyme AKR1C9
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
in the CNS: both reaction directions by type 3 isozyme AKR1C2
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
-
last step in neurosteroid allopregnanolone biosynthesis
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
NADH-linked, particulate enzyme prefers oxidative reaction, while the NADPH-linked, cytosolic enzyme prefers the reductive reaction
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
-
r
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
discussion of physiological role
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate, fluorometric activity measurement in intact cells, overview
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, NADPH and NADH possible as cofactors
-
?
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase activity, utilizing NADH as cofactor when of particulate origin and NADPH when of cytosolic origin
-
r
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnane-3alpha-ol-20-one + NAD(P)+
-
activity higher during lactation in female rats
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5alpha-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
r
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
?
5beta-pregnan-3,20-dione + NAD(P)H
3alpha-hydroxy-5beta-pregnan-20-one + NAD(P)+
-
3alpha-hydroxysteroid-5beta-oxidoreductase activity
-
r
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
a 3alpha-hydroxysteroid + NAD+
a 3-oxosteroid + NADH + H+
-
-
-
r
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
progesterone
allopregnanolone
-
r
pregn-4-en-3,20-dione + NADPH + H+
3alpha-hydroxypregn-4-en-20-one + NADP+
progesterone
allopregnanolone
-
r
additional information
?
-
-
broad substrate range
-
-
?
additional information
?
-
the enzyme catalyzes reversibly the oxidoreduction of 3alpha-hydroxyl groups of steroid hormones
-
-
?
additional information
?
-
the enzyme catalyzes reversibly the oxidoreduction of 3alpha-hydroxyl groups of steroid hormones
-
-
?
additional information
?
-
-
type 3 isoform in liver virtually identical with bile acid-binding protein
-
-
?
additional information
?
-
due to inhibition by NADPH, the isozymes acts only as 3-ketosteroid reductases in vivo
-
-
?
additional information
?
-
-
due to inhibition by NADPH, the isozymes acts only as 3-ketosteroid reductases in vivo
-
-
?
additional information
?
-
-
enzyme inactivates steroid hormones in the liver, regulates 5alpha-dihydrotestosterone levels in the prostate, and forms the neurosteroid allopregnanolone in the CNS, isozymes might be involved in regulation of the levels of active androgens, estrogens, and progestrins
-
-
?
additional information
?
-
in vivo the isozymes act predominantly as 3-ketosteroid reductases due to inhibition by NADPH, but significantly produce 3beta-tetrahydrosteroids physiologically important in steroid metabolim, androgen metabolism, overview
-
-
?
additional information
?
-
-
in vivo the isozymes act predominantly as 3-ketosteroid reductases due to inhibition by NADPH, but significantly produce 3beta-tetrahydrosteroids physiologically important in steroid metabolim, androgen metabolism, overview
-
-
?
additional information
?
-
-
isozyme AKR1C2 is involved in neurosteroid biosynthesis, while isozyme AKE1C1 eliminates the neurosteroid precursor from the pathway and decreases the neurosteroid concentration in the brain, pathway overview
-
-
?
additional information
?
-
-
physiological roles of the isozymes AKR1C1-4, overview, enzyme regulates the occupancy and trans-activation of steroid hormone receptors by interconverting potent hormones with their cognate inactive metabolites
-
-
?
additional information
?
-
-
role of the isozymes in bile acid biosynthesis and steroid metabolism, product profiling, pre-receptor regulation of steroid hormone action, overview
-
-
?
additional information
?
-
-
AKR1C3 catalyzes androgen, estrogen, and prostaglandin metabolism, AKR1C3 is also involved in cancer development or progression
-
-
?
additional information
?
-
-
type I human hepatic 3alpha-hydroxysteroid dehydrogenase plays a significant role in bile acid biosynthesis, steroid hormone metabolism, and xenobiotic metabolism, the enzyme is regulated by expression level of the liver X receptor alpha, i.e. LXRalpha [NR1H3], a nuclear hormone receptor, predictive response element modeling and whole genome analysis of LXRalpha occupancy sites using ChIP/microarray technology, overview
-
-
?
additional information
?
-
-
belongs to the group of Y'bile acid binders, bile acid metabolizing enzymes
-
-
?
additional information
?
-
-
belongs to the group of Y'bile acid binders, bile acid metabolizing enzymes
-
-
?
additional information
?
-
-
enzyme inactivates steroid hormones in the liver, regulates 5alpha-dihydrotestosterone levels in the prostate, and forms the neurosteroid allopregnanolone in the CNS
-
-
?
additional information
?
-
-
enzyme plays a pivotal role in the inactivation of circulating steroid hormones
-
-
?
additional information
?
-
-
enzyme regulates the occupancy and trans-activation of steroid hormone receptors by interconverting potent hormones with their cognate inactive metabolites
-
-
?
additional information
?
-
-
the high 3alpha-oxidoreductase activity in the hypothalamus of prepubertal rats is not related to the gonadal or adrenal steroids, the products are found in both prepubertal, mature, and castrated rats, rats with adrenalectomy show elevated enzyme activities, 3alpha-hydroxy progesterone is not related to the regulation of gonadotropin secretion in the male rat
-
-
?
additional information
?
-
-
AKR1C9 catalyzes androgen, estrogen, and prostaglandin metabolism
-
-
?
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0.017 - 0.042
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
0.069
(3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.0027
(5beta,20R)-20-hydroxypregnan-3-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.022 - 0.14
1-Acenaphthenol
0.002 - 0.0024
17beta-hydroxy-5alpha-androstan-3-one
0.0007 - 0.0017
17beta-hydroxy-5beta-androstan-3-one
0.0007 - 0.00075
3-oxo-5beta-cholan-24-oic acid
-
-
0.0031
3alpha-androstanediol
-
pH 7.0, 25°C, recombinant enzyme
0.0014
3alpha-hydroxy-5alpha-pregnan-20-one
-
oxidation
0.005
3alpha-tetrahydroprogesterone
-
-
0.2 - 0.8
4-Nitroacetophenone
-
also in this range: 2,3-hexanedione, 1-phenyl-1,2-propanedione, 2,3-pentanedione, pyridine-4-aldehyde, 2,3-butanedione
0.087
4-nitrobenzaldehyde
-
NADPH, detection spectrophotometrically
0.0012 - 0.007
5alpha-androstan-3,17-dione
0.00065 - 0.0031
5alpha-androstane-3,17-dione
0.0006 - 0.026
5alpha-dihydroprogesterone
0.0001 - 0.07103
5alpha-dihydrotestosterone
0.000082
5alpha-pregnan-3,20-dione
-
reduction
0.00016 - 0.0016
5beta-androstan-3,17-dione
0.0012 - 0.007
5beta-androstane-3,17-dione
0.018
5beta-Dihydrocortisol
-
-
0.00051 - 0.0012
5beta-dihydroprogesterone
0.235
5beta-Pregnan-3alpha-ol-20-one
-
cytosolic NADH-linked 5beta-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
0.0024
5beta-pregnane-3,20-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.023
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.021 - 0.038
9,10-phenanthrenequinone
0.003
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one
-
recombinant enzyme in intact COS-1 cells
0.0015
allopregnanolone
-
pH 7.0, 25°C
0.004 - 0.0422
androstanedione
0.0001 - 0.21
androsterone
0.017 - 1.8
benzenedihydrodiol
0.03 - 0.077
Camphorquinone
-
4-nitrobenzaldehyde, 2,3-heptanedione
0.063
chenodeoxycholic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.004
Dehydrolithocholic acid
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.42
diacetyl
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.00315
dihydrotestosterone
37°C, pH not specified in the publication
0.0061 - 0.037
Fusidic acid
0.038
glycocholic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.0052 - 0.0059
glycolithocholic acid
0.022
isatin
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.068
lithocholic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.0025
oxidized 8-acetyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one
-
isozyme AKR1C3
0.00084 - 0.00213
pregn-4-en-3,20-dione
0.043
taurocholic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.0028 - 0.119
testosterone
additional information
additional information
-
0.017
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
NADP+, detection spectrophotometrically
0.019
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
NADP+, detection radio- or fluorometrically
0.022
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
pH 7.0, 37°C with NADP+
0.042
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
pH 7.0, 37°C with NAD+
0.022
1-Acenaphthenol
-
pH 7.4, 25°C, recombinant isozyme AKR1C1 and isozyme AKR1C2
0.07
1-Acenaphthenol
-
pH 7.4, 25°C, recombinant isozyme AKR1C3
0.14
1-Acenaphthenol
-
pH 7.4, 25°C, recombinant isozyme AKR1C4
0.048
1-Indanol
-
pH 7.4, 25°C, recombinant isozyme AKR1C1
0.17
1-Indanol
-
pH 7.4, 25°C, recombinant isozyme AKR1C4
0.94
1-Indanol
-
pH 7.4, 25°C, recombinant isozyme AKR1C2
1.4
1-Indanol
-
pH 7.4, 25°C, recombinant isozyme AKR1C3
0.002 - 0.0024
17beta-hydroxy-5alpha-androstan-3-one
-
-
0.002 - 0.0024
17beta-hydroxy-5alpha-androstan-3-one
-
also in this range: 3alpha,7alpha-dihydroxy-5beta-cholanoyl glycine
0.0007 - 0.00075
17beta-hydroxy-5beta-androstan-3-one
-
testis
0.0012 - 0.0017
17beta-hydroxy-5beta-androstan-3-one
-
also in this range: 5beta-dihydrotestosterone, rat epididymis
0.0012 - 0.0017
17beta-hydroxy-5beta-androstan-3-one
-
also in this range: 17alpha,21-dihydroxy-5beta-pregnan-3,11,20-trione, acenaphthequinone
0.0012
5alpha-androstan-3,17-dione
wild-type, pH 7.5, 25°C
0.0012
5alpha-androstan-3,17-dione
wild type enzyme, in 0.1 M HEPES at pH 7.5
0.0022
5alpha-androstan-3,17-dione
mutant N86A, pH 7.5, 25°C
0.0031
5alpha-androstan-3,17-dione
mutant enzyme S114A, in 0.1 M HEPES at pH 7.5
0.005
5alpha-androstan-3,17-dione
mutant Y155F, pH 7.5, 25°C
0.007
5alpha-androstan-3,17-dione
mutant K159A, pH 7.5, 25°C
0.00065
5alpha-androstane-3,17-dione
-
pH 7.0, 25, reduction reaction
0.0012
5alpha-androstane-3,17-dione
wild-type, pH 7.5, 25°C
0.0031
5alpha-androstane-3,17-dione
mutant S114A, pH 7.5, 25°C
0.0006
5alpha-dihydroprogesterone
-
pH 7.0, 25°C, isozyme AKR1C2
0.0011
5alpha-dihydroprogesterone
-
pH 7.0, 25°C, isozyme AKR1C1
0.0018
5alpha-dihydroprogesterone
-
pH 7.0, 25°C
0.026
5alpha-dihydroprogesterone
-
isozyme AKR1C3
0.0001
5alpha-dihydrotestosterone
-
-
0.00062 - 0.00065
5alpha-dihydrotestosterone
-
-
0.0013
5alpha-dihydrotestosterone
-
recombinant enzyme in intact COS-1 cells
0.00218
5alpha-dihydrotestosterone
pH 7.4, 37°C, recombinant wild-type enzyme
0.0029
5alpha-dihydrotestosterone
-
pH 7.0, 25°C, recombinant enzyme
0.003415
5alpha-dihydrotestosterone
37°C, pH 7.2
0.006
5alpha-dihydrotestosterone
-
NADP+, detection radiometrically
0.007 - 0.0083
5alpha-dihydrotestosterone
-
-
0.007 - 0.0083
5alpha-dihydrotestosterone
-
also in this range: androstanedione
0.007 - 0.0083
5alpha-dihydrotestosterone
-
also in this range: 3alpha,12alpha-dihydroxy-5beta-cholanoyl glycine
0.007 - 0.0083
5alpha-dihydrotestosterone
-
also in this range: 3alpha-hydroxy-5alpha-androstan-17-one
0.007 - 0.0083
5alpha-dihydrotestosterone
-
also in this range: 3alpha-hydroxy-5beta-pregnan-17-one
0.012
5alpha-dihydrotestosterone
-
-
0.018
5alpha-dihydrotestosterone
-
NADPH, detection radiometrically
0.019
5alpha-dihydrotestosterone
-
NADPH, detection spectrophotometrically
0.0223
5alpha-dihydrotestosterone
-
-
0.026
5alpha-dihydrotestosterone
-
pH 7.0, 37°C, with NAD(P)H
0.07103
5alpha-dihydrotestosterone
pH 7.4, 37°C, recombinant mutant V54L
0.00016
5beta-androstan-3,17-dione
-
-
0.00035 - 0.00049
5beta-androstan-3,17-dione
-
also in this range: 5beta-pregnan-3,20-dione, 5alpha-androstan-3,17-dione
0.0016
5beta-androstan-3,17-dione
-
-
0.0012
5beta-androstane-3,17-dione
wild-type, pH 7.5, 25°C
0.0021
5beta-androstane-3,17-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.0022
5beta-androstane-3,17-dione
mutant N86A, pH 7.5, 25°C
0.005
5beta-androstane-3,17-dione
mutant Y155F, pH 7.5, 25°C
0.007
5beta-androstane-3,17-dione
mutant K159A, pH 7.5, 25°C
0.00051
5beta-dihydroprogesterone
-
pH 7.0, 37°C
0.0007
5beta-dihydroprogesterone
-
pH 7.0, 25°C, isozyme AKR1C2
0.0012
5beta-dihydroprogesterone
-
pH 7.0, 25°C, isozyme AKR1C1
0.021
9,10-phenanthrenequinone
-
NADPH, detection spectrophotometrically
0.038
9,10-phenanthrenequinone
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.004
androstanedione
-
NADPH, detection spectrophotometrically
0.0422
androstanedione
-
-
0.0001
androsterone
-
-
0.00044
androsterone
-
pH 9.0, 25°C, recombinant His-tagged mutant S114A/Y155F
0.0035
androsterone
-
pH 7.4, 25°C, recombinant isozyme AKR1C2 and isozyme AKR1C4
0.0041
androsterone
-
pH 7.0, 25, oxidation reaction
0.0051
androsterone
pH 10.4, 25°C, recombinant wild-type enzyme
0.0055
androsterone
-
pH 9.0, 25°C, recombinant His-tagged wild-type
0.007
androsterone
-
pH 9.0, 25°C, recombinant His-tagged mutant S114A
0.033
androsterone
pH 10.4, 25°C, recombinant mutant K159A
0.048
androsterone
-
NADP+, detection radiometrically
0.065
androsterone
-
pH 9.0, 25°C, recombinant His-tagged mutant K159A
0.074
androsterone
-
pH 9.0, 25°C, recombinant His-tagged mutant Y155F
0.1
androsterone
-
pH 9.0, 25°C, recombinant His-tagged mutant Y155F/K159A
0.21
androsterone
-
pH 8.5, 37°C, with cofactor NAD+
0.017
benzenedihydrodiol
-
pH 7.4, 25°C, recombinant isozyme AKR1C4
0.15
benzenedihydrodiol
-
pH 7.4, 25°C, recombinant isozyme AKR1C1
0.32
benzenedihydrodiol
-
pH 7.4, 25°C, recombinant isozyme AKR1C3
1.8
benzenedihydrodiol
-
pH 7.4, 25°C, recombinant isozyme AKR1C2
0.015
cholate
-
-
56
cholate
37°C, pH 8.0, wild-type enzyme
78
cholate
37°C, pH 8.0, mutant enzyme S114A/Y153F
96
cholate
37°C, pH 8.0, mutant enzyme K157A
468
cholate
37°C, pH 8.0, mutant enzyme Y153F
586
cholate
37°C, pH 8.0, mutant enzyme S114A
0.01 - 0.025
cholic acid
-
-
0.01 - 0.025
cholic acid
-
3alpha-hydroxy-5beta-androstan-17-one, 3alpha,21-dihydroxy-5beta-pregnan-20-one, 5beta-androstan-3alpha,17beta-diol, 5alpha-androstan-3alpha,17beta-diol, NADP+
0.01 - 0.025
cholic acid
-
NAD+, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl glycine
0.031
cholic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.084
cholic acid
-
pH 8.5, 37°C, with cofactor thio-NAD+
51
dehydrocholate
37°C, pH 8.0, wild-type enzyme
239
dehydrocholate
37°C, pH 8.0, mutant enzyme S114A
2489
dehydrocholate
37°C, pH 8.0, mutant enzyme Y153F
0.0061
Fusidic acid
-
-
0.0062
Fusidic acid
-
pH 8.5, 37°C, with cofactor NAD+
0.037
Fusidic acid
-
pH 8.5, 37°C, with cofactor thio-NAD+
0.0052 - 0.0059
glycolithocholic acid
-
-
0.0052 - 0.0059
glycolithocholic acid
-
also in this range: 3alpha-hydroxy-5alpha-pregnan-20-one
0.00305
NAD+
mutant D249S, pH 10.2, 25°C
0.0038
NAD+
wild type enzyme, in 0.1 M CAPS buffer, at pH 10.2, at 25°C
0.0038
NAD+
wild-type, pH 10.2, 25°C
0.005
NAD+
mutant enzyme D249S, in 0.1 M CAPS buffer, at pH 10.2, at 25°C
0.009
NAD+
mutant enzyme D249K, in 0.1 M CAPS buffer, at pH 10.2, at 25°C
0.009
NAD+
mutant D249K, pH 10.2, 25°C
0.016
NAD+
mutant enzyme D249A, in 0.1 M CAPS buffer, at pH 10.2, at 25°C
0.016
NAD+
mutant D249A, pH 10.2, 25°C
0.004
NADH
wild-type, pH 7.5, 25°C
0.004
NADH
wild type enzyme, in 0.1 M HEPES at pH 7.5
0.0065
NADH
mutant enzyme S114A, in 0.1 M HEPES at pH 7.5
0.0065
NADH
mutant S114A, pH 7.5, 25°C
0.01
NADH
mutant N86A, pH 7.5, 25°C
0.029
NADH
mutant Y155F, pH 7.5, 25°C
0.4
NADH
-
cytosolic NADH-linked 5beta-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
0.00023
NADP+
-
pH 7.0, 25°C
0.00007
NADPH
-
pH 7.0, 25°C
0.91
NADPH
-
cytosolic NADH-linked 5beta-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
1.33
NADPH
-
microsomal NADPH-linked 5beta-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
0.00084
pregn-4-en-3,20-dione
pH 7.4, 37°C, recombinant wild-type enzyme
0.00213
pregn-4-en-3,20-dione
pH 7.4, 37°C, recombinant mutant V54L
0.0028
testosterone
-
-
0.012
testosterone
-
NADP+, detection radiometrically
0.119
testosterone
-
pH 7.4, 35°C, 3alpha-hydroxysteroid dehydrogenase activity
additional information
additional information
-
-
-
additional information
additional information
-
kinetics
-
additional information
additional information
-
kinetics
-
additional information
additional information
-
values for various substrates and different isozymes
-
additional information
additional information
-
steady-state kinetics
-
additional information
additional information
-
steady-state kinetics
-
additional information
additional information
steady-state kinetics
-
additional information
additional information
-
cofactor binding kinetics
-
additional information
additional information
-
kinetic mechanism, substrate binding mechanism of isozyme AKR1C2
-
additional information
additional information
-
kinetic mechanism, substrate binding mechanism of isozyme AKR1C9, wild-type and mutant enzymes
-
additional information
additional information
-
kinetic modeling of an enzymatic cycling reaction
-
additional information
additional information
steady state kinetics, overview
-
additional information
additional information
-
steady state kinetics, overview
-
additional information
additional information
-
steady-state kinetics, ternary complex, sequential, kinetic mechanism of allopregnanolone synthesis with the cofactor binding before the steroid and leaving after it
-
additional information
additional information
-
equilibrium kinetics of wild-type and mutant enzymes
-
additional information
additional information
-
transient single and multiple turnover kinetics, stopped flow kinetics, isotope kinetics, ligand binding analysis, kinetics with deuterium-substituted cofactor and binary complex of enzyme and cofactor, overview
-
additional information
additional information
-
cofactor kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
-
kinetics in absence and presence of co-solvents, overview
-
additional information
additional information
kinetics of wild-type and mutant enzymes in presence or absence of CAPS and methylamine, overview
-
additional information
additional information
-
steady-state, transient state kinetics, and kinetic isotope effects, kinetic analysis and mechanism, ordered bi-bi mechanism, detailed overview
-
additional information
additional information
steady-state kinetics, and stopped-flow study, kinetics of enzyme mutants P185A, P185G, T188A, and T188S showing an increase in kcat, Ka drosterone and KiNAD and equal primary isotope effects of DV and D(V/K)
-
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MacDonald, I.A.; Jellett, J.F.; Mahony, D.E.; Holdeman, L.V.
Bile salt 3alpha- and 12alpha-hydroxysteroid dehydrogenases from Eubacterium lentum and related organisms
Appl. Environ. Microbiol.
37
992-1000
1979
Eggerthella lenta
brenda
Mahony, D.E.; Meier, C.E.; MacDonald, I.A.; Holdeman, L.V.
Bile salt degradation by nonfermentative clostridia
Appl. Environ. Microbiol.
34
419-423
1977
Asaccharospora irregularis
brenda
MacDonald, I.A.; Mahony, D.E.; Jellet, J.F.; Meier, C.E.
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Butylated hydroxyanisole alters rat 5alpha-reductase and 3alpha-hydroxysteroid dehydrogenase Implications for influences of neurosteroidogenesis
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Rattus norvegicus (P23457)
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