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3 alpha-hydroxysteroid dehydrogenase
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3-alpha hydroxysteroid dehydrogenase type 3
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3alpha-hydroxysteroid dehydrogenase
3alpha-hydroxysteroid dehydrogenase type 3
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3alpha-hydroxysteroid dehydrogenase/carbonyl reductase
3alpha-hydroxysteroid oxido-reductase
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3alpha-hydroxysteroid oxidoreductase
3alpha-hydroxysteroid-5beta-oxidoreductase
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3alpha-oxidoreductase
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3alpha/3beta-hydroxysteroid dehydrogenase
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5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
aldo-keto reductase 1C2
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bile-acid binding protein
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i.e. type 3 isozyme AKR1C2
chlordecone reductase
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i.e. type 1 isozyme AKR1C4
DD2
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i.e. type 3 isozyme AKR1C2
DD21
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i.e. isozyme AKR1C1
dihydrodiol dehydrogenase
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i.e. type 1 isozyme AKR1C4
hydroxyprostaglandin dehydrogenase
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NAD(P)+-3alpha-hydroxysteroid dehydrogenase
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NAD+-dependent 3alpha-HSD
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NADP(H)-dependent 3alpha-HSD
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NADPH:5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
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prostaglandin F2alpha-synthase
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i.e. type 2 isozyme AKR1C3
sterognost 3alpha dehydrogenase, 3alpha-hydroxy steroid
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type 2 3alpha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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type 3 3alpha-hydroxysteroid dehydrogenase
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type 5 17beta-hydroxysteroid dehydrogenase
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i.e. type 2 isozyme AKR1C3
3alpha-HSD
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3alpha-HSD/CR
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3alpha-HSD3
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3alpha-HSOR
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
-
3alpha-hydroxysteroid dehydrogenase
-
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
-
3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase
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3alpha-hydroxysteroid dehydrogenase/carbonyl reductase
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3alpha-hydroxysteroid dehydrogenase/carbonyl reductase
-
3alpha-hydroxysteroid oxidoreductase
-
NADH- and NADPH-linked
3alpha-hydroxysteroid oxidoreductase
-
3alpha-hydroxysteroid oxidoreductase
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-
3alphaHSD
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3HSD
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5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
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5alpha-dihydroprogesterone 3alpha-hydroxysteroid oxidoreductase
-
NADH- and NADPH-linked
AKR1C
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AKR1C9
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HSD
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HSD28
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hsdA
-
additional information
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cf. EC 1.1.1.184
additional information
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cf. EC 1.1.1.213
additional information
cf. EC 1.1.1.213
additional information
cf. EC 1.1.1.213, the enzyme belongs to the short chain dehydrogenase/reductase protein superfamily
additional information
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cf. 1.1.1.213, the enzyme belongs to the aldo-keto reductase subfamily AKR1C
additional information
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cf. EC 1.1.1.213
additional information
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cf. EC 1.1.1.213, the enzyme belongs to the aldo-keto reductase subfamily AKR1C
additional information
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cf. EC 1.1.1.213, the enzyme belongs to the aldo-keto reductase, AKR, superfamily
additional information
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enzyme belongs to the AKR1C subfamily of the AKR superfamily of enzymes
additional information
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enzyme belongs to the aldo-keto reductase AKR superfamily
additional information
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enzyme belongs to the aldo-keto reductase superfamily
additional information
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enzymes belongs to the aldo-keto reductase superfamily
additional information
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the isozymes belong to the AKR1C subfamily of the aldo-keto-reductase AKR superfamily
additional information
the isozymes belong to the AKR1C subfamily of the aldo-keto-reductase AKR superfamily
additional information
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the enzyme belongs to the short-chain dehydrogenase/reductase, SDR, superfamily
additional information
cf. EC 1.1.1.213, the enzyme belongs to the AKR1C family
additional information
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cf. EC 1.1.1.213
additional information
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cf. EC 1.1.1.213
additional information
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cf. EC 1.1.1.213
additional information
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cf. EC 1.1.1.213
additional information
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cf. EC 1.1.1.213, the enzyme belongs to the short-chain dehydrogenase/reductase family
additional information
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cf. EC 1.1.1.213, the enzyme is a member of the aldo-keto reductase superfamily
additional information
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enzyme belongs to the aldo-keto reductase AKR superfamily
additional information
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enzyme belongs to the aldo-keto reductase superfamily
additional information
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enzyme belongs to the aldo-keto reductase superfamily
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
reaction mechanism
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
reaction mechanism: ordered bi bi with random substrate binding and ordered release of product, NADPH is released last, pro-R-hydrogen atom of NAD(P)H is transferred to carbonyl substrate
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
enzyme isoforms bind substrate in different ways
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
isozymes AKR1C1 and AKR1C2 are bifunctional enzymes also showing minor 20alpha-hydroxysteroid dehydrogenase activity, EC 1.1.1.149
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
isozymes also performs 17- and 20-ketosteroid reductase and 3alpha-, 17beta- and 20alpha-hydroxysteroid oxidase activities at varying rates
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
ordered bi bi kinetic mechanism, catalytic residues are Y55 and H117
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
ordered bi bi kinetic reaction mechanism with nucleotide cofactor binding first
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
steroid binding pocket structure of isozyme AKR1C2
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
steroid binding pocket structure of isozyme AKR1C9
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
steroid substrate recognition mechanism by isozymes AKR1C1-AKR1C4, Tyr55 is involved in catalysis, ordered bi bi mechanism
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
the catalytic triad is composed of Ser-114, Tyr-155, and Lys-159, structural analysis and sequence alignment of the short chain dehydrogenase/reductase family
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
the reduction reaction is slightly preferred by the wild-type enzyme, which is determined by residue Arg276
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
bi bi ordered mechanism, kinetic analysis, overview
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
the enzyme shows a sequential ordered reaction mechanism, where NAD+ binds to the enzyme first and NADH leaves last
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a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
The overall oxidoreductive reaction comprises the deprotonation of tyrosine, proton abstraction by the tyrosinate anion, and hydride transfer from the hydroxysteroid to NAD+, followed by the release of a proton from the hydroxy group of tyrosine to the solution. The proton transfer to the external base, from Tyr155 to Lys159 via 2'-OH of ribose, with a late transition state is the rate-limiting step, mechanism, overview
a 3alpha-hydroxysteroid + NAD(P)+ = a 3-oxosteroid + NAD(P)H + H+
rate-limiting step in the reaction is the release of NADH and proton. P185, T188 and the flexible substrate-binding loop are involved in binding with the nucleotide cofactor and with androsterone and are also involved in catalysis, catalytic mechanism, overview
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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+
?
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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+
?
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?
1-acenaphthenol + NADP+
?
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isozymes AKR1C1-AKR1C4
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r
1-acenaphthenol + NADPH
?
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?
1-acetophenone + NADPH
1-phenylethanol + NADP+
-
-
-
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?
1-indanol + NADP+
?
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isozymes AKR1C1-AKR1C4
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r
17beta-estradiol + NADP+
estrone + NADPH
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-
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r
17beta-hydroxy-dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
-
-
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r
2-decalol + NAD+
? + NADH + H+
-
-
-
?
3-hydroxysteroid + NAD(P)+
3-ketosteroid + NAD(P)H
-
-
-
?
3-oxocholic acid + NADPH
3alpha-hydroxycholic acid + NADP+
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reverse reaction rate negligible
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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
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-
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r
3alpha,17beta-androstene-3,17-diol + NAD(P)+
dihydrotestosterone + NAD(P)H + H+
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-
?
3alpha,21-dihydroxy-5beta-pregnan-20-one + NADP+
21-hydroxy-5beta-pregnan-3,20-dione + NADPH
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-
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r
3alpha,5alpha,20alpha-trihydroxyprogesterone + NADP+
5alpha,20alpha-dihydroxyprogesterone-3-one + NADPH + H+
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-
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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
-
-
-
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?
3alpha-adiol + NAD(P)+
dihydrotestosterone + NAD(P)H
3alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH
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oxidation utilizing NAD+ as a cofactor is the preferred reaction in vitro
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r
3alpha-hydroxy-12-oxo-9,11-cholenic acid + NADP+
3,12-dioxo-9,11-cholenic acid + NADPH
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-
-
-
?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH
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?
3alpha-hydroxy-5alpha-pregnan-20-one + NADP+
5alpha-pregnan-3,20-dione + NADPH + H+
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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+
-
-
-
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?
3alpha-hydroxytibolone + NAD+
tibolone + NADH
isozymes AKR1C2 and AKR1C4, no activity with isozyme AKR1C1
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r
3alpha-tetrahydroprogesterone + NADH
5alpha-dihydroprogesterone + NAD+
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r
3beta-hydroxytibolone + NAD+
tibolone + NADH
isozymes AKR1C2, AKR1C1, and AKR1C4
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r
4'-methoxyacetophenone + NADPH + H+
1-(4-methoxyphenyl)ethanol + NADP+
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R,S-enantiomeric product
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?
4-androsten-3alpha-ol-17-one + NADH + H+
4-androsten-3alpha,17beta-diol + NAD+
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AKR1C17
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r
4-androstene-3,17-dione + NADH + H+
4-androsten-3alpha-ol-17-one + NAD+
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low activity
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r
4-bromoacetophenone + NADPH + H+
1-(4-bromophenyl)ethanol + NADP+
-
-
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?
4-cyanoacetophenone + NADPH + H+
1-(4-cyanophenyl)ethanol + NADP+
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?
4-methylacetophenone + NADPH + H+
1-(4-methylphenyl)ethanol + NADP+
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R,S-enantiomeric product
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?
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+
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-
-
?
5alpha-androstan-3,17-dione + NADPH + H+
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
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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+
-
-
-
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r
5alpha-androstane-3,17-dione + NADH
5alpha-androstan-3alpha-ol-17-one + NAD+
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low activity
AKR1C9
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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+
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isozymes AKR1C1-AKR1C4
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r
5alpha-dihydroprogesterone + NADPH + H+
3alpha,5alpha-3-hydroxypregnan-20-one + NADP+
5alpha-dihydroprogesterone + NADPH + H+
5alpha-hydroxy-pregnan-20-one + NADP+
-
isozyme AKR1C2
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?
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
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r
5alpha-dihydrotestosterone + NADH
?
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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
1.1.1.50 3alpha-hydroxysteroid 3-dehydrogenase (Si-specific)
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