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Information on EC 1.1.1.64 - testosterone 17beta-dehydrogenase (NADP+)
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EC Tree
1.1.1.64 testosterone 17beta-dehydrogenase (NADP+)IUBMB Comments
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
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Word Map
- 1.1.1.64
- androgen
- testis
- 17beta-hsd3
- androstenedione
- testicular
- leydig
- hsd17b3
-
steroidogenic
-
puberty
-
5alpha-reductase
- pseudohermaphroditism
-
genitalia
-
dehydrogenase-3
- estrone
- p450scc
- medicine
- drug development
- diagnostics
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
17betahsd3, 17beta-hydroxysteroid dehydrogenase 3, 17beta-hsd 3, testosterone 17beta-dehydrogenase (nadp+), 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-ketoreductase
-
-
-
-
17beta-HSD 3
17beta-HSD3
17beta-hydroxysteroid dehydrogenase
17beta-hydroxysteroid dehydrogenase 3
17beta-hydroxysteroid dehydrogenase type 3
AKR1C3
HSD17B3
NADP-dependent testosterone-17beta-oxidoreductase
-
-
-
-
type 3 17beta-HSD
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NADP+ = androstenedione + NADPH + H+
4-pro-S-hydrogen atom of NADPH is transferred to the alpha-face of the steroid molecule
-
testosterone + NADP+ = androstenedione + NADPH + H+
4-pro-R-hydrogen atom of NADPH is transferred to the alpha-face of the steroid molecule
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testosterone + NADP+ = androstenedione + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
17beta-hydroxysteroid:NADP+ 17-oxidoreductase
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
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CAS REGISTRY NUMBER
COMMENTARY
9028-63-1
-
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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
1,2,3,4-tetrahydro-1-naphthol + NADP+
1,2,3,4-tetrahydro-1-naphthone + NADPH
-
isoenzymes 1 and 2
-
r
1-acenaphthenol + NADP+
1-acenaphthenone + NADPH
-
isoenzymes 1 and 2
-
r
19-nortestosterone + NADP+
19-norandrostenedione + NADPH
-
93% activity compared to testosterone oxidation
-
r
5alpha-androstane-17beta-ol-3-one + NADP+
5alpha-androstane-3,17-dione + NADPH
-
30% activity compared to testosterone oxidation
-
r
5alpha-dihydrotestosterone + NADP+
5alpha-17-oxo-dihydrotestosterone + NADPH
-
isoenzymes 1 and 2
-
r
5beta-androstane-17beta-ol + NADP+
5alpha-androstane-17-one + NADPH
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117% activity compared to testosterone oxidation
-
r
5beta-androstane-17beta-ol-3-one + NADP+
5beta-androstane-3,17-dione + NADPH
-
330% activity compared to testosterone oxidation
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r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
5beta-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
-
-
-
-
r
benzene dihydrodiol + NADP+
o-benzoquinone + NADPH
-
isoenzymes 1 and 2
-
r
cyclohex-2-en-1-ol + NADP+
cyclohex-2-en-1-one + NADPH
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isoenzymes 1 and 2
-
r
dehydroepiandrosterone + NADPH
androst-5-ene-3beta,17beta-diol + NADP+
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-
-
r
pyridine-4-aldehyde + NADPH
pyridine-4-alcohol + NADP+
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isoenzymes 1 and 2
-
r
additional information
?
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-
human 17beta-hydroxysteroid dehydrogenases are multifunctional enzymes, isozyme 17beta-HSD4 also performs beta-oxidation of branched fatty acids, like pristanic acid, and in bile acid synthesis, e.g. of di- and trihydroxycholestanoic acids, overview
-
-
?
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
-
93% activity compared to testosterone oxidation
-
r
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
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63% activity compared to testosterone oxidation
-
r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
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25% activity compared to testosterone oxidation
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r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
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134% activity compared to testosterone oxidation
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r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
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1180% activity compared to testosterone oxidation
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r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
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-
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r
5beta-dihydrotestosterone + NADP+
5beta-17-oxo-dihydrotestosterone + NADPH
-
-
-
-
?
5beta-dihydrotestosterone + NADP+
5beta-17-oxo-dihydrotestosterone + NADPH
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isoenzymes 1 and 2
-
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
the enzyme plays a central role in the development of the male phenotype. Mutations that inactivate the enzyme give rise to a rare form of male pseudohermaphroditism, referred to as 17beta-HSD-3 deficiency
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
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convertion of the weak androgen androstendione into the potent androgen testosterone
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-
?
androstenedione + NADPH + H+
testosterone + NADP+
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-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
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the equilibrium state is 92% testosterone to 8% androstenedione
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r
androstenedione + NADPH + H+
testosterone + NADP+
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the enzyme is involved in biosynthesis of testosterone
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-
?
androstenedione + NADPH + H+
testosterone + NADP+
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i.e. 4-androsten-17-ol-3-one
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?
androstenedione + NADPH + H+
testosterone + NADP+
the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1.146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
i.e. 4-androsten-17beta-ol-3-one
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?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
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NADP+ is preferred
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r
testosterone + NAD+
androstenedione + NADH
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NAD+ shows ess than 10% of the activity with NADP+
-
-
ir
testosterone + NAD+
androstenedione + NADH
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NAD+ shows 20% of the activity with NADP+
-
-
ir
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysteroid dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysteroid dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
-
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
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-
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
rate of oxidation is less than 30% of those for reduction
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r
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
-
-
-
r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
NADP+ is preferred
-
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
the enzyme plays a central role in the development of the male phenotype. Mutations that inactivate the enzyme give rise to a rare form of male pseudohermaphroditism, referred to as 17beta-HSD-3 deficiency
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
convertion of the weak androgen androstendione into the potent androgen testosterone
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
-
the enzyme is involved in biosynthesis of testosterone
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1.146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
i.e. 4-androsten-17beta-ol-3-one
-
?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
-
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
-
-
r
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
isoenzyme 1, 40% of its NADP+ dependent activity, isoenzyme 2, less than 5% of its NADP+ dependent activity