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(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (R)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
i.e. (S)-tetralol
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
-
-
-
?
(S)-camphorquinone + NADH + H+
? + NAD+
(S)-camphorquinone + NADPH + H+
? + NADP+
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
-
-
-
?
1-acenaphthenol + NAD+
acenaphthylen-1(2H)-one + NADH + H+
-
-
-
?
1-phenyl-1,2-propanedione + NADH + H+
? + NAD+
-
-
-
?
11alpha-hydroxytestosterone + NAD+
11alpha-hydroxyandrost-4-ene-3,17-dione + NADH
-
156% velocity compared to testosterone
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
15alpha-hydroxytestosterone + NAD+
15alpha-hydroxyandrost-4-ene-3,17-dione + NADH
-
131% velocity compared to testosterone
-
r
16-oxoestrone + NADH + H+
? + NAD+
-
-
-
?
17beta-estradiol + NAD+
? + NADH + H+
-
-
-
r
17beta-estradiol + NAD+
estrone + NADH + H+
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one + NAD+
1alpha-methyl-5alpha-androstane-3,17-dione + NADH
-
192% velocity compared to testosterone
-
r
17beta-hydroxy-5beta-androstan-3-one + NAD+
5beta-androstane-3,17-dione + NADH
-
86% velocity compared to testosterone
-
r
2,3-butanedione + NADH + H+
? + NAD+
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
2-[(2-bromoethyl)(2-[[(2-hydroxyethyl)amino]methyl]-4,6-dinitrophenyl)amino]ethyl methanesulfonate + 2 NADH + 2 H+
2-[(2-bromoethyl)[4-(hydroxyamino)-2-[[(2-hydroxyethyl)amino]methyl]-6-nitrophenyl]amino]ethyl methanesulfonate + 2 NAD+ + H2O
-
i.e. PR-104A, phosphate ester prodrug designed to exploit tumor hypoxia
i.e. PR-104H, enzyme acts as nitroreductase for activation of PR-104A
-
?
20alpha-hydroxyprogesterone + NADH + H+
? + NAD+
-
-
-
?
3alpha-hydroxyprogesterone + NADH + H+
? + NAD+
-
-
-
?
3beta-hydroxy-5alpha-androstane-17-one + NAD+
5alpha-androstane-3,17-dione + NADH
-
75% velocity compared to testosterone
-
r
3beta-hydroxyprogesterone + NADH + H+
? + NAD+
-
-
-
?
4-androstenedione + NADPH + H+
testosterone + NADP+
-
-
-
-
?
4-oxo-2-nonenal + NADPH + H+
4-hydroxy-2-nonenal + NADP+
-
-
-
?
4-pregnen-3alpha-ol-2-one + NAD+
4-pregnen-3,20-dione + NADH + H+
-
-
-
r
4-pregnen-3alpha-ol-20-one + NAD+
4-pregnen-3,20-dione + NADH + H+
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD+
5alpha-androstan-3alpha-ol-17-one + NADH
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
5alpha-androstan-3beta-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
5alpha-androstane-3,17-dione + NADH + H+
? + NAD+
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
5alpha-androstane-3alpha,17beta-diol + NAD+
?
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
5alpha-androstane-3beta,17beta-diol + NAD+
?
-
-
-
?
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
5alpha-dihydrotestosterone + NAD+
androstandione + NADH + H+
-
-
-
r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH + H+
5alpha-pregnan-20alpha-ol-3-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3,21alpha-diol-20-one + NAD+
5alpha-pregnan-21-ol-3,20-dione + NADH
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
5beta-androstan-3alpha-ol-17-one + NADH
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
5beta-androstane-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
r
5beta-androstane-3,17-dione + NADH + H+
? + NAD+
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
5beta-androstane-3alpha-ol-17-one + NADH
-
57% velocity compared to testosterone
-
r
5beta-androstane-3alpha,17beta-diol + NAD+
?
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
5beta-androstane-3beta,17beta-diol + NAD+
?
-
-
-
?
5beta-dihydrotestosterone + NAD+
androstanedione + NADH + H+
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha,21-diol-20-one + NAD+
5beta-pregnan-21-ol-3,20-dione + NADH
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
5beta-pregnan-3beta,21-diol-20-one + NAD+
?
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH + H+
? + NAD+
-
-
-
?
6beta-hydroxytestosterone + NAD+
6beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
84% velocity compared to testosterone
-
r
9,10-phenanthrenequinone + NADH + H+
? + NAD+
-
-
-
?
alpha-3-hydroxyhexobarbital + NAD+
?
-
-
-
?
alpha-tetralone + NADH + H+
? + NAD+
-
-
-
?
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH
-
75% velocity compared to testosterone
-
r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
-
-
-
-
?
androst-5-ene-3beta,17beta-diol + NAD+
androst-5-ene-3beta-ol-17-one + NADH
-
33% velocity compared to testosterone
-
r
androstandiol + NAD+
androsterone + NADH
-
-
-
r
androstanediol + NAD+
androsterone + NADH
-
-
-
r
benzene dihydrodiol + NAD+
?
-
-
-
?
benzene dihydrodiol + NAD+
? + NADH + H+
-
-
-
?
beta-3-hydroxyhexobarbital + NAD+
?
-
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
cis-benzene dihydrodiol + NAD+
?
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
dehydroepiandrosterone + NAD+
? + NADH + H+
-
-
-
?
estradiol + NAD+
estrone + NADH
estrone + NADPH + H+
17beta-estradiol + NADP+
-
-
-
-
?
farnesol + NAD+
?
-
-
-
?
farnesol + NAD+
? + NADH + H+
-
-
-
?
farnesol + NAD+
farnesal + NADH + H+
-
-
-
?
geraniol + NAD+
?
-
-
-
?
geraniol + NAD+
? + NADH + H+
-
-
-
?
geraniol + NAD+
geranial + NADH + H+
-
-
-
?
geranylgeraniol + NAD+
?
-
-
-
?
geranylgeraniol + NAD+
? + NADH + H+
-
-
-
?
geranylgeraniol + NAD+
geranylgeranial + NADH + H+
-
-
-
?
glycochenodeoxycholic acid + NAD+
7alpha-hydroxy-3-oxo-5-beta-cholanoyl glycine + NADH
-
-
-
?
glycolithocholic acid + NAD+
3-oxo-5beta-cholanoyl glycine + NADH
-
-
-
?
isatin + NADH + H+
? + NAD+
-
-
-
?
lithocholic acid
5beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
lithocholic acid + NAD+
5-beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
morphine + NAD+
morphinone + NADH + H+
reaction of EC 1.1.1.218
-
-
?
naphthalene dihydrodiol + NAD+
? + NADH + H+
-
-
-
?
nerol + NAD+
neral + NADH + H+
-
-
-
?
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
-
-
-
-
?
pyridine-3-aldehyde + NADH + H+
? + NAD+
-
-
-
?
testosterone + NAD+
4-androstenedione + NADH + H+
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
testosterone + NAD+
androstenedione + NADH + H+
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
NADP is 3fold less efficient as cofactor
-
r
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
r
trans-benzene dihydrodiol + NAD+
?
-
-
-
?
additional information
?
-
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+

3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
-
-
r
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
-
-
?
(S)-1-indanol + NAD+

2,3-dihydro-1H-inden-1-one + NADH + H+
-
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
-
-
-
?
(S)-camphorquinone + NADH + H+

? + NAD+
-
-
-
?
(S)-camphorquinone + NADH + H+
? + NAD+
-
-
-
?
11beta-hydroxytestosterone + NAD+

11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
136% velocity compared to testosterone
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
-
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
76% of testosterone oxidation rate
-
r
17beta-estradiol + NAD+

estrone + NADH + H+
-
-
-
?
17beta-estradiol + NAD+
estrone + NADH + H+
-
-
-
?
2-cyclohexen-1-ol + NAD+

2-cyclohexen-1-one + NADH + H+
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+

5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+

5alpha-androstane-3alpha-ol-17-one + NADH
-
72% velocity compared to testosterone
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
-
204% velocity compared to testosterone
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+

? + NADH + H+
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
r
5alpha-androstane-3beta,17beta-diol + NAD+

5alpha-androstane-3beta-ol-17-one + NADH
-
72% velocity compared to testosterone
-
r
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
-
17% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NAD+

5alpha-androstane-3,17-dione + NADH + H+
-
133% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
-
-
-
?
5alpha-dihydrotestosterone + NAD+

androstanedione + NADH + H+
-
-
-
r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH + H+
-
119% initial velocity compared to testosterone
-
r
5alpha-pregnan-3alpha-ol-20-one + NAD+

5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
r
5beta-androstan-17beta-ol-3-one + NAD+

5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+

5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
r
5beta-androstane-3alpha,17beta-diol + NAD+

? + NADH + H+
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
r
5beta-dihydrotestosterone + NAD+

androstanedione + NADH + H+
-
-
-
?
5beta-dihydrotestosterone + NAD+
androstanedione + NADH + H+
-
50% initial velocity compared to testosterone
-
r
5beta-pregnan-3alpha-ol-20-one + NAD+

5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
r
beta-ionol + NAD+

(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
-
-
?
daunorubicin + NADPH + H+

daunorubicinol + NADP+
inactivation of the anticancer drug
-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
the enzyme reduces daunorubicin to its corresponding alcohol daunorubicinol using NADPH as the coenzyme
-
-
r
estradiol + NAD+

estrone + NADH
-
72% velocity compared to testosterone oxidation
-
r
estradiol + NAD+
estrone + NADH
-
-
-
r
estradiol + NAD+
estrone + NADH
-
46% of testosterone oxidation rate
-
r
estradiol + NAD+
estrone + NADH
-
15% velocity compared to testosterone oxidation
-
r
testosterone + NAD+

4-androstenedione + NADH + H+
-
-
-
?
testosterone + NAD+
4-androstenedione + NADH + H+
-
-
-
?
testosterone + NAD+

androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
?
testosterone + NAD+

androstenedione + NADH + H+
-
-
-
r
testosterone + NAD+
androstenedione + NADH + H+
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
-
-
r
testosterone + NAD+
androstenedione + NADH + H+
-
-
-
r
additional information

?
-
the enzyme AKR1C34 shows 3alpha/17beta/20alpha-hydroxysteroid dehydrogenase activities, substrate specificity, detailed overview. Ala54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS). AKR1C34 also has morphine dehydrogenase activity, EC 1.1.1.218. No activity with cyclohexanol
-
-
?
additional information
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residues Tyr118 and Phe310 play key roles in ligand binding in AKR1C27 and AKR1C28, Glu276 that is a critical residue for the NAD+ specificity is conserved in the enzymes. In the reverse reaction, the enzymes reduces several a-dicarbonyl compounds including scamphorquinone using NADH as the coenzyme. The enzyme oxidizes 3alpha- and 17beta-hydroxysteroids and also shows S-tetralol dehydrogenase activity, cf. EC 1.1.1.121 and (S)-specific secondary alcohol dehydrogenase. AKR1C28 exhibits low dehydrogenase activity for 20alpha-hydroxysteroids, but does not oxidize 3beta-hydroxysteroids (5alpha/beta-androstan-3beta-ol-17-ones and 5alpha/beta-pregnan-3beta-ol-20-ones), 17alpha-hydroxysteroids (4-androsten-17alpha-ol-3-one and 17alpha-estradiol) and 20beta-hydroxysteroids (4-pregnene-17alpha/20beta-diol-3-one and 5alpha-pregnan-20beta-ol-3-one). In the NADH-linked reverse reaction, AKR1C28 highly reduces non-steroidal alpha-dicarbonyl compounds, and also exhibits moderate activities towards TBE, alpha-tetralone and pyridine-3-aldehyde. AKR1C28 shows higher kcat/Km values for 17beta-hydroxy-C19-steroids than those for 3alpha-hydroxysteroids, and most efficiently oxidized 17beta-estradiol. Substrate specificity, overview
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additional information
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J7M9D0
residues Tyr118 and Phe310 play key roles in ligand binding in AKR1C27 and AKR1C28, Glu276 that is a critical residue for the NAD+ specificity is conserved in the enzymes. In the reverse reaction, the enzymes reduces several a-dicarbonyl compounds including scamphorquinone using NADH as the coenzyme. The enzyme oxidizes 3alpha- and 17beta-hydroxysteroids and also shows S-tetralol dehydrogenase activity, cf. EC 1.1.1.121 and (S)-specific secondary alcohol dehydrogenase. AKR1C28 exhibits low dehydrogenase activity for 20alpha-hydroxysteroids, but does not oxidize 3beta-hydroxysteroids (5alpha/beta-androstan-3beta-ol-17-ones and 5alpha/beta-pregnan-3beta-ol-20-ones), 17alpha-hydroxysteroids (4-androsten-17alpha-ol-3-one and 17alpha-estradiol) and 20beta-hydroxysteroids (4-pregnene-17alpha/20beta-diol-3-one and 5alpha-pregnan-20beta-ol-3-one). In the NADH-linked reverse reaction, AKR1C28 highly reduces non-steroidal alpha-dicarbonyl compounds, and also exhibits moderate activities towards TBE, alpha-tetralone and pyridine-3-aldehyde. AKR1C28 shows higher kcat/Km values for 17beta-hydroxy-C19-steroids than those for 3alpha-hydroxysteroids, and most efficiently oxidized 17beta-estradiol. Substrate specificity, overview
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