1.1.1.239: 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

This is an abbreviated version, for detailed information about 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+), go to the full flat file.

Reaction

testosterone
+
NAD+
=
androstenedione
+
NADH
+
H+

Synonyms

17-ketoreductase, 17beta-HSD, 17beta-hydroxysteroid dehydrogenase type 5, 3alpha(17beta)-HSD, AKR1C3, aldo-keto reductase 1C3, dehydrogenase, 3alpha,17beta-hydroxy steroid, type 2 3alpha-hxdroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase, type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase, type 3 17beta-hydroxysteroid dehydrogenase, type 5 beta-hydroxysteroid dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.239 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

Substrates Products

Substrates Products on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
show the reaction diagram
-
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
11alpha-hydroxytestosterone + NAD+
11alpha-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
156% velocity compared to testosterone
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
15alpha-hydroxytestosterone + NAD+
15alpha-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
131% velocity compared to testosterone
-
r
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one + NAD+
1alpha-methyl-5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
192% velocity compared to testosterone
-
r
17beta-hydroxy-5beta-androstan-3-one + NAD+
5beta-androstane-3,17-dione + NADH
show the reaction diagram
-
86% velocity compared to testosterone
-
r
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
show the reaction diagram
-
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
-
-
3beta-hydroxy-5alpha-androstane-17-one + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
75% velocity compared to testosterone
-
r
4-androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
4-oxo-2-nonenal + NADPH + H+
4-hydroxy-2-nonenal + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD+
5alpha-androstan-3alpha-ol-17-one + NADH
show the reaction diagram
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
show the reaction diagram
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
show the reaction diagram
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
133% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NAD+
androstandione + NADH
show the reaction diagram
-
-
-
r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH
show the reaction diagram
5alpha-pregnan-3,21alpha-diol-20-one + NAD+
5alpha-pregnan-21-ol-3,20-dione + NADH
show the reaction diagram
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NAD+
5beta-androstan-3alpha-ol-17-one + NADH
show the reaction diagram
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
5beta-androstane-3alpha-ol-17-one + NADH
show the reaction diagram
-
57% velocity compared to testosterone
-
r
5beta-dihydrotestosterone + NAD+
androstanedione + NADH
show the reaction diagram
-
50% initial velocity compared to testosterone
-
r
5beta-pregnan-3alpha,21-diol-20-one + NAD+
5beta-pregnan-21-ol-3,20-dione + NADH
show the reaction diagram
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH
show the reaction diagram
-
-
-
?
6beta-hydroxytestosterone + NAD+
6beta-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
84% velocity compared to testosterone
-
r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH
show the reaction diagram
-
75% velocity compared to testosterone
-
r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
show the reaction diagram
-
-
-
-
?
androst-5-ene-3beta,17beta-diol + NAD+
androst-5-ene-3beta-ol-17-one + NADH
show the reaction diagram
-
33% velocity compared to testosterone
-
r
androstandiol + NAD+
androsterone + NADH
show the reaction diagram
-
-
-
r
androstanediol + NAD+
androsterone + NADH
show the reaction diagram
-
-
-
r
estradiol + NAD+
estrone + NADH
show the reaction diagram
estrone + NADPH + H+
17beta-estradiol + NADP+
show the reaction diagram
-
-
-
-
?
glycochenodeoxycholic acid + NAD+
7alpha-hydroxy-3-oxo-5-beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
?
glycolithocholic acid + NAD+
3-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
-
-
-
?
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
show the reaction diagram
-
NADP is 3fold less efficient as cofactor
-
r