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Information on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)
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EC Tree
1.1.1.239 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)IUBMB Comments
Also acts on other 17beta-hydroxysteroids and on the 3alpha-hydroxy group of pregnanes and bile acids. Different from EC 1.1.1.50 3alpha-hydroxysteroid dehydrogenase (Si-specific) or EC 1.1.1.213 3alpha-hydroxysteroid dehydrogenase (Re-specific).
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Word Map
- 1.1.1.239
- androgen
- estradiol
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steroidogenic
- akr1c3
- androstenedione
- prostate
- 3beta-hsd
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3beta-hydroxysteroid
- estrone
- aromatase
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steroidogenesis
-
5alpha-reductase
- dehydroepiandrosterone
- leydig
- 3alpha-hsds
-
3alpha-hydroxysteroid
- p450scc
- 5alpha-dihydrotestosterone
-
cochliobolus
-
4-dione
- androsterone
- lunatus
- delta5-3beta-hsd
-
intracrine
- coumestrol
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5alpha-dht
- pseudohermaphroditism
- p450arom
- 4-androstene-3,17-dione
- medicine
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
17beta-hsd, aldo-keto reductase 1c3, type 5 17beta-hsd, 17beta-hydroxysteroid dehydrogenase type 5, 17-ketoreductase, type 3 17beta-hydroxysteroid dehydrogenase, type 5 17beta-hydroxysteroid dehydrogenase, type 2 3alpha-hsd, akr1c28, testosterone 17beta-dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-ketoreductase
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17beta-HSD
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3,17beta-HSD
3,17beta-hydroxysteroid dehydrogenase
3alpha(17beta)-HSD
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AKR1C3
aldo-keto reductase 1C3
dehydrogenase, 3alpha,17beta-hydroxy steroid
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EC 1.1.1.63
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formerly
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NAD+-dependent 3alpha(17beta)-hydroxysteroid dehydrogenase
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NAD+-dependent 3beta(17beta)-hydroxysteroid dehydrogenase
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PGER6
type 2 3alpha-hxdroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
additional information
AKR1C3
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multi-functional enzyme that possesses 3alpha-, 17beta-, 20alpha-hydroxysteroid dehydrogenase, as well as prostaglandine F synthase activities and catalyzes androgen, estrogen, progestin and prostaglandin metabolism. It is a member of the aldo-keto reductase superfamily.
type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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additional information
cf. EC 1.1.1.218, morphine 6-dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+
random mechanism
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testosterone + NAD+ = androst-4-ene-3,17-dione + NADH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3alpha(or 17beta)-hydroxysteroid:NAD+ oxidoreductase
Also acts on other 17beta-hydroxysteroids and on the 3alpha-hydroxy group of pregnanes and bile acids. Different from EC 1.1.1.50 3alpha-hydroxysteroid dehydrogenase (Si-specific) or EC 1.1.1.213 3alpha-hydroxysteroid dehydrogenase (Re-specific).
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CAS REGISTRY NUMBER
COMMENTARY
126469-82-7
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9028-62-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (R)-tetralol
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-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
i.e. (S)-tetralol
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-
?
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
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156% velocity compared to testosterone
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r
15alpha-hydroxytestosterone + NAD+
15alpha-hydroxyandrost-4-ene-3,17-dione + NADH
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131% velocity compared to testosterone
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r
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one + NAD+
1alpha-methyl-5alpha-androstane-3,17-dione + NADH
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192% velocity compared to testosterone
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r
17beta-hydroxy-5beta-androstan-3-one + NAD+
5beta-androstane-3,17-dione + NADH
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86% velocity compared to testosterone
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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
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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
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?
3beta-hydroxy-5alpha-androstane-17-one + NAD+
5alpha-androstane-3,17-dione + NADH
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75% velocity compared to testosterone
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r
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+
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-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD+
5alpha-androstan-3alpha-ol-17-one + NADH
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-
-
?
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+
-
-
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r
5alpha-androstane-3,17-dione + NADH + H+
? + NAD+
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-
-
?
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
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-
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?
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
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-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH
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-
-
?
5beta-androstan-3alpha,17beta-diol + NAD+
5beta-androstan-3alpha-ol-17-one + NADH
-
-
-
?
5beta-androstane-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
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r
5beta-androstane-3,17-dione + NADH + H+
? + NAD+
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-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
5beta-androstane-3alpha-ol-17-one + NADH
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57% velocity compared to testosterone
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r
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
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-
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?
5beta-pregnan-3alpha,21-diol-20-one + NAD+
5beta-pregnan-21-ol-3,20-dione + NADH
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-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH
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-
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?
5beta-pregnan-3beta-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
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?
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH + H+
? + NAD+
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?
6beta-hydroxytestosterone + NAD+
6beta-hydroxyandrost-4-ene-3,17-dione + NADH
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84% velocity compared to testosterone
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r
9,10-phenanthrenequinone + NADH + H+
? + NAD+
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?
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH
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75% velocity compared to testosterone
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r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
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?
androst-5-ene-3beta,17beta-diol + NAD+
androst-5-ene-3beta-ol-17-one + NADH
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33% velocity compared to testosterone
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r
glycochenodeoxycholic acid + NAD+
7alpha-hydroxy-3-oxo-5-beta-cholanoyl glycine + NADH
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?
glycolithocholic acid + NAD+
3-oxo-5beta-cholanoyl glycine + NADH
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?
lithocholic acid
5beta-cholan-3-one-24-oic acid + NADH + H+
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?
lithocholic acid + NAD+
5-beta-cholan-3-one-24-oic acid + NADH + H+
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?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
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?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH + H+
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?
morphine + NAD+
morphinone + NADH + H+
reaction of EC 1.1.1.218
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?
naphthalene dihydrodiol + NAD+
? + NADH + H+
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?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
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NADP is 3fold less efficient as cofactor
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r
testosterone + NADP+
androstenedione + NADPH + H+
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r
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
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-
r
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
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-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
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-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
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?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
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?
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
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136% velocity compared to testosterone
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r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
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-
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r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
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76% of testosterone oxidation rate
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r
17beta-estradiol + NAD+
estrone + NADH + H+
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-
-
?
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
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72% velocity compared to testosterone
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r
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
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204% velocity compared to testosterone
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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
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72% velocity compared to testosterone
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r
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
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17% velocity compared to testosterone
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r
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
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133% velocity compared to testosterone
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r
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH + H+
-
-
-
?
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH + H+
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119% initial velocity compared to testosterone
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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
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-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
the enzyme reduces daunorubicin to its corresponding alcohol daunorubicinol using NADPH as the coenzyme
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-
r
estradiol + NAD+
estrone + NADH
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72% velocity compared to testosterone oxidation
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r
estradiol + NAD+
estrone + NADH
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46% of testosterone oxidation rate
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r
estradiol + NAD+
estrone + NADH
-
15% velocity compared to testosterone oxidation
-
r
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+
androstenedione + NADH + H+
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
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-
r
testosterone + NAD+
androstenedione + NADH + H+
-
-
-
r
additional information
?
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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
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?
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
?
-
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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