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Enzyme Nomenclature
Information on EC 1.1.1.145 - 3beta-hydroxy-DELTA5-steroid dehydrogenase
for references in articles please use BRENDA:EC1.1.1.145
Word Map on EC 1.1.1.145
- 1.1.1.145
-
steroidogenic
- adrenal
-
steroidogenesis
- cyp11a1
-
star
- progesterone
-
androgen
- leydig
- ovarian
- estrogen
- follicle
- gonad
-
granulosa
- testicular
-
adrenocortical
- lutein
- androstenedione
- dehydroepiandrosterone
- aldosterone
- aromatase
- cortisol
- dheas
- pregnenolone
- hsd17b3
- p450scc
-
theca
- srd5a1
-
lhcgr
- 21-hydroxylase
-
virilization
- akr1c3
- sult2a1
-
reticularis
- genitalia
-
nci-h295r
- hyperandrogenism
- 17alpha-hydroxylase
-
scarb1
-
steroidogenesis-related
- hypospadias
- nutrition
-
salt-wasting
- 17-hydroxyprogesterone
- trilostane
- medicine
- p450arom
-
aldosterone-producing
-
adrenarche
- 17-hydroxypregnenolone
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.1.1.145
-
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RECOMMENDED NAME
GeneOntology No.
3beta-hydroxy-DELTA5-steroid dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
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-
-
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a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
catalytic residues are Lys159 and Tyr154, structure/function analysis of isozyme 1; catalytic residues are Lys159 and Tyr154, structure/function analysis of isozyme 2
a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
structure-function relationship
-
a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
substrate binding and active site residues, overview
a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
enzyme forms a ternary complex with NAD+ binding before sterol binding
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
-
redox reaction
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-
-
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reduction
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
3beta-hydroxy-DELTA5-steroid:NAD+ 3-oxidoreductase
This activity is found in several bifunctional enzymes that catalyse the oxidative conversion of Delta5-3-hydroxy steroids to a Delta4-3-oxo configuration. This conversion is carried out in two separate, sequential reactions; in the first reaction, which requires NAD+, the enzyme catalyses the dehydrogenation of the 3beta-hydroxy steroid to a 3-oxo intermediate. In the second reaction the reduced coenzyme, which remains attached to the enzyme, activates the isomerization of the Delta5 form to a Delta4 form (cf. EC 5.3.3.1, steroid Delta-isomerase). Substrates include dehydroepiandrosterone (which is converted into androst-5-ene-3,17-dione), pregnenolone (converted to progesterone) and cholest-5-en-3-one, an intermediate of cholesterol degradation.
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CAS REGISTRY NUMBER
COMMENTARY
9044-85-3
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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389371, 389372, 389388, 389389, 389395, 655345, 656091, 656577, 656657, 656788, 668413, 670036, 687967, 693887, 699845, 700182, 713188, 725816, 740418, 740914, 740998, 741261, 741423
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389377, 389378, 389379, 389380, 389395, 389396, 389399, 656586, 656655, 657352, 688664, 688674, 690002, 699845, 740247
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bifunctional enzyme that also catalyzes the reaction of the steroid DELTA5-DELTA4 isomerase, EC 5.3.3.1; large White and Meishan pigs, bifunctional enzyme
SwissProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
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isoform 3betaHSD2 associates with the inner mitochondrial membrane but does not integrate into the membrane. 3betaHSD2 forms a transient association with the translocases Tim50 and Tom22 and with Tim23. This association occurs primarily through the interaction of Tim50 with the N-terminus of 3betaHSD2 and contributes to enzymatic activity. Tim50 knockdown inhibits catalysis of dehydroepiandrostenedione to androstenedione and pregnenolone to progesterone. Although Tim50 knockdown decreases 3betaHSD2 expression, restoration of expression via proteasome and protease inhibition does not rescue activity
metabolism
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the content of steroidogenic acute regulatory protein StAR, CYP11A1 and HSD3B1 mRNAs and the secretion of progesterone and androstenedione is modulated by adiponectin in endometrial and myometrial tissue explants during early pregnancy and the oestrous cycle. adiponectin affects basal and insulin-stimulated expression of key steroidogenic genes and production of steroid hormones by the porcine uterus during maternal recognition of pregnancy and implantation
metabolism
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isoform 3betaHSD2 interacts with the mitochondrial translocase, Tim50, to regulate progesterone and androstenedione formation
metabolism
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isoform HSD3B1 is involved in aldosterone production in aldosterone-producing adenoma
metabolism
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isoform 3bHSD2 interacts with the mitochondrial translocase, Tim50, to regulate progesterone and androstenedione formation
metabolism
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isoform 3bHSD2 interacts with the mitochondrial translocase, Tim50, to regulate progesterone and androstenedione formation
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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
11beta,17alpha,21-trihydroxy-4-pregnen-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-4-pregnen-20-one + NADP+
-
-
-
-
?
11beta,17alpha,21-trihydroxy-5alpha-pregnane-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-5alpha-pregnan-20-one + NADP+
-
-
-
-
?
11beta,17alpha,21-trihydroxy-5beta-pregnane-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-5beta-pregnan-20-one + NADP+
-
-
-
-
?
17-hydroxyprogesterone + NADPH
3beta,17-dihydroxy-4-pregnen-20-one + NADP+
-
-
-
-
?
17beta-hydroxy-5alpha-androstane-3-one + NADPH
3beta,17beta-dihydroxy-5alpha-androstane + NADP+
-
-
-
-
?
17beta-hydroxy-5beta-androstane-3-one + NADPH
3beta,17beta-dihydroxy-5beta-androstane + NADP+
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
3beta,7alpha-dihydroxy-5-cholestenoic acid + NAD+
7alpha-hydroxy-3-oxo-5-cholestenoic acid + NADH
-
-
-
-
?
4-androsten-17beta-ol-3-one + NADH + H+
4-androsten-3beta,17beta-diol + NAD+
-
-
-
r
5-androsten-3beta-ol-17-one + NAD+
5-androsten-3,17-dione + NADH
-
-
-
r
5alpha-androstane-3,17-dione + NADPH
3beta-hydroxy-5alpha-androstane-17-one + NADP+
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
5alpha-androstane-3beta-ol-17-one + NADP+
-
-
-
-
r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-17beta-ol-3-one + NADPH
-
-
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3beta,17beta-diol + NADP+
-
-
-
-
?
5alpha-pregnane-3,20-dione + NADH
5alpha-pregnane-3beta-ol-20-one + NAD+
-
-
-
r
5alpha-pregnane-3beta-ol-20-one + NAD+
5alpha-pregnane-3,20-dione + NADH
-
-
-
r
5alpha-pregnane-3beta-ol-20-one + NADP+
5alpha-pregnane-3,20-dione + NADPH
-
-
-
-
r
5beta-androstan-17beta-ol-3-one + NADPH
5beta-androstane-3beta,17beta-diol + NADP+
-
-
-
-
r
5beta-androstan-3beta-ol-17-one + NADP+
5beta-androstane-3,17-dione + NADPH
-
-
-
-
r
5beta-androstane-3,17-dione + NADPH
3beta-hydroxy-5beta-androstane-17-one + NADP+
-
-
-
-
?
5beta-androstane-3,17-dione + NADPH
5beta-androstan-3beta-ol-17-one + NADP+
-
-
-
-
r
5beta-androstane-3beta,17beta-diol + NADP+
5beta-androstan-17beta-ol-3-one + NADPH
-
-
-
-
r
5beta-pregnan-20alpha-ol-3-one + NADPH + H+
5beta-pregnan-3beta,20alpha-diol + NADP+
-
-
-
-
r
5beta-pregnan-3beta-ol-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
-
-
-
-
r
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnane-3beta-ol-20-one + 5beta-pregnane-3alpha-ol-20-one + NAD+
-
-
-
r
5beta-pregnane-3,20-dione + NADPH + H+
5beta-pregnan-3beta-ol-20-one + NADP+
-
-
-
-
r
5beta-pregnane-3beta,20alpha-diol + NADP+
5beta-pregnane-20alpha-ol-3-one + NADPH + H+
-
-
-
-
r
5beta-pregnane-3beta-ol-20-one + NAD+
5beta-pregnane-3,20-dione + NADH + H+
-
-
-
r
6-tert-butyl-2,3-epoxy-5-cyclohexene-1,4-dione + NADPH
? + NADP+
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major product has S-configuration
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-
r
7alpha,25-dihydroxycholesterol + NAD+
7alpha,25-dihydroxy-4-cholesten-3-one + NADH
-
-
-
-
?
7alpha,27-dihydroxycholesterol + NAD+
7alpha,27-dihydroxy-4-cholesten-3-one + NADH
-
-
-
-
?
7alpha-hydroxycholesterol + NAD+
7alpha-hydroxy-4-cholesten-3-one + NADH
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-
-
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?
benzil + NADPH
(R)-benzoin + NADP+
-
enantiomeric purity of 97% enantiomeric excess
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r
pregnenolone + NAD+
isoprogesterone + progesterone + NADH
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about 90% odf product is isoprogesterone
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r
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
-
-
-
?
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
-
-
-
-
?
3beta-hydroxy-5-androsten-17-one + NAD+
androstendione + NADH + H+
-
-
-
-
?
3beta-hydroxy-5-androsten-17-one + NAD+
androstendione + NADH + H+
-
-
-
-
?
5-pregnen-3beta-ol-2-one + NAD+
progesterone + NADH
-
trivial name pregnenolone
-
-
?
5alpha-androstan-3beta-ol-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
-
-
5alpha-androstan-3beta-ol-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
-
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
?
5beta-pregnane-3,20-dione + NAD(P)H + H+
5beta-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
r
5beta-pregnane-3,20-dione + NAD(P)H + H+
5beta-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
r
5beta-pregnane-3,20-dione + NAD(P)H + H+
5beta-pregnane-3beta-ol-20-one + NAD(P)+
-
-
-
-
?
androst-5-ene-3beta-ol-17-one + NAD+
androst-5-ene-3,17-dione + NADH
-
-
-
-
ir
androst-5-ene-3beta-ol-17-one + NAD+
androst-5-ene-3,17-dione + NADH
-
-
-
-
ir
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH + H+
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH + H+
-
-
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
-
the enzyme is essential for biosynthesis of all classes of steroid hormones, molecular mechanisms of enzyme regulation involving the Nur77 family of immediate-early orphan nuclear receptors, e.g. Nur77 targets the promoter of gene HSD3B2 in testicular Leygig cells, overview
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
-
the enzyme performs the 3beta-hydroxysteroid dehydrogenase and DELTA5-DELTA4 isomerase reactions
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
the enzyme is essential for biosynthesis of all classes of steroid hormones
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
the enzyme performs the 3beta-hydroxysteroid dehydrogenase and DELTA5-DELTA4 isomerase reactions
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
the enzyme is essential for biosynthesis of all classes of steroid hormones
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
the enzyme performs the 3beta-hydroxysteroid dehydrogenase and DELTA5-DELTA4 isomerase reactions
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
sitosterol + NAD+
3-oxo-24-ethyl-cholest-5-ene + NADH + H+
-
the enzyme is involved in the catabolic pathway for the degradation of sitosterol to androstenedione
-
-
?
sitosterol + NAD+
3-oxo-24-ethyl-cholest-5-ene + NADH + H+
-
the enzyme is involved in the catabolic pathway for the degradation of sitosterol to androstenedione
-
-
?
additional information
?
-
-
no reaction with OH in 3alpha, 17beta, 11beta, 21 position
-
-
-
additional information
?
-
-
the enzyme is regulated on expression not on catalytic activity level
-
-
-
additional information
?
-
-
trifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, and of the 17beta-hydroxysteroid dehydrogenase type II, EC 1.1.1.51
-
-
-
additional information
?
-
-
enzyme catalyzes at least two reactions in the cardenolide pathway, i.e. dehydrogenation of pregnenolone to isoprogesterone and the reduction of 5beta-pregnane-3,20-dione to 5beta-pregnan-3beta-ol-20-one. Recombinant enzyme displays 3alpha-, 3beta- and 17beta-dehydrogenase as well as 3/17-keto reductase activities
-
-
-
additional information
?
-
enzyme catalyzes at least two reactions in the cardenolide pathway, i.e. dehydrogenation of pregnenolone to isoprogesterone and the reduction of 5beta-pregnane-3,20-dione to 5beta-pregnan-3beta-ol-20-one. Recombinant enzyme displays 3alpha-, 3beta- and 17beta-dehydrogenase as well as 3/17-keto reductase activities
-
-
-
additional information
?
-
the enzyme is essential for biosynthesis of all classes of steroid hormones catalyzing the first step of the multienzyme pathway conversion of circulating dehydroepiandrosterone and pregnenolone to active steroid hormones
-
-
-
additional information
?
-
the enzyme is essential for biosynthesis of all classes of steroid hormones, pathway overview
-
-
-
additional information
?
-
the enzyme is essential for biosynthesis of all classes of steroid hormones, pathway overview
-
-
-
additional information
?
-
-
the enzyme is involved in steroid production and/or metabolism
-
-
-
additional information
?
-
bifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1
-
-
-
additional information
?
-
bifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1
-
-
-
additional information
?
-
bifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1
-
-
-
additional information
?
-
bifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1
-
-
-
additional information
?
-
-
enzyme exhibits high stereo-selectivity yielding 3-beta-hydroxysteroids from 3-ketosteroids
-
-
-
additional information
?
-
using fluorescence resonance energy transfer, it is shown that 3betaHSD2 interacts strongly with a mixture of dipalmitoylphosphatidylglycerol and dipalmitoylphosphatidylcholine
-
-
-
additional information
?
-
enzyme diplays lipid-mediated unfolding. As isoform 3betaHSD2 lacks a receptor, opening the conformation may activate the protein by forming a cavity forms between the alpha-helix and beta-sheet
-
-
-
additional information
?
-
-
metabolic conversion assays indicate peak 3betaHSD2 activity at pH 4.5 with 2fold more progesterone synthesized at pH 4.5 than at pH 3.5 and 7.4. Increasing the 3betaSD2 concentration from 1 to 40 microg results in a 7fold increase in progesterone at pH 4.5, but no change at pH 7.4
-
-
-
additional information
?
-
-
no reaction with OH in 17alpha, 17beta, 20alpha, 20beta position
-
-
-
additional information
?
-
-
specific for 3beta-OH group in steroids with trans configuration of A/B rings and DELTA5-double bond
-
-
-
additional information
?
-
relationship between the expression of hepatic but not testicular enzyme with androstenone deposition in pig adipose tissue, overview
-
-
-
additional information
?
-
bifunctional enzyme that also catalyzes the reaction of the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
P14060, P26439
-
-
-
?
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
-
-
-
-
?
5-pregnen-3beta-ol-2-one + NAD+
progesterone + NADH
-
trivial name pregnenolone
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
P14060, P26439
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
-
-
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
-
the enzyme is essential for biosynthesis of all classes of steroid hormones, molecular mechanisms of enzyme regulation involving the Nur77 family of immediate-early orphan nuclear receptors, e.g. Nur77 targets the promoter of gene HSD3B2 in testicular Leygig cells, overview
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
Q0G9Z6
the enzyme is essential for biosynthesis of all classes of steroid hormones
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
Q0G9Z6
the enzyme is essential for biosynthesis of all classes of steroid hormones
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
-
-
-
-
?
additional information
?
-
-
the enzyme is regulated on expression not on catalytic activity level
-
-
-
additional information
?
-
P14060
the enzyme is essential for biosynthesis of all classes of steroid hormones catalyzing the first step of the multienzyme pathway conversion of circulating dehydroepiandrosterone and pregnenolone to active steroid hormones
-
-
-
additional information
?
-
P14060
the enzyme is essential for biosynthesis of all classes of steroid hormones, pathway overview
-
-
-
additional information
?
-
P26439
the enzyme is essential for biosynthesis of all classes of steroid hormones, pathway overview
-
-
-
additional information
?
-
-
the enzyme is involved in steroid production and/or metabolism
-
-
-
additional information
?
-
P26439
using fluorescence resonance energy transfer, it is shown that 3betaHSD2 interacts strongly with a mixture of dipalmitoylphosphatidylglycerol and dipalmitoylphosphatidylcholine
-
-
-
additional information
?
-
Q9N119
relationship between the expression of hepatic but not testicular enzyme with androstenone deposition in pig adipose tissue, overview
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
NADH forms hydrogen bond with Asp35 in the NADH-wild-type 3beta-HSD1 complex
NAD+
-
-
389371, 389385, 389386, 389387, 389388, 389389, 389395, 389401, 668423, 670036, 693887, 699845, 700182, 740914, 740998, 741261, 741423
NADP+
-
NADPH forms hydrogen bond with Lys36 in the NADPH-wild-type 3beta-HSD1 complex. The total contribution of Asp35 and Lys36 is most favorable in the case of NADPH binding to the wild-type enzyme when compared with NADH, and Lys36 have strong electronic interaction with NADPH
additional information
-
no reaction with 3-acetylpyridine-adenine dinucleotide, nicotinamide-hypoxanthine dinucleotide, 3-acetylpyridine-hypoxanthine dinucleotide
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
-
(1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
(1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
(1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
(1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
-
(1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
-
(1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
4-nonylphenol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
diethylhexyl phthalate
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
diethylstilbestrol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
ketoconazole
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
octylphenol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
tributyltin
-
0.012 mM, almost complete loss of activity; complete inhibition at 0.012 mM, the inhibition mechanism is not entirely competitive, overview
epostane
; inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 14–17fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y; inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 14–17fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y
epostane
inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2
trilostane
-
i.e. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-en-2-carbonitrile
trilostane
-
i.e. 2alpha-cyano-4alpha,5alpha-epoxy-17beta-ol-androstane-3-one, competitive inhibition
trilostane
-
human adrenal H295R cells treated with the HSD3B2 inhibitor, trilostane, demonstrate a markedly decreased androstenedione production
trilostane
inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2. Trilostane is docked in the active site of isoform 3beta-HSD1, and residue Arg195 in 3beta-HSD1 is a potentially critical residue
trilostane
-
0.005 mM, 56% inhibition, 0.025 mM, 90% inhibition; potent inhibition
trilostane
-
treatment does not affect transcription or translation in liver or adrenal
additional information
-
no inhibition by quercetin, apigenin, genistein, daidzein, enterodiol, and enterolactone
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
testosterone
-
at low dose, increase in mRNA expression. At doses above 0.2 mg/kg/day, downregulation of 3beta-hydroxysteroid dehydrogenase mRNA
additional information
-
hypoxia-inducible factor-1alpha potentially regulates 3beta-hydroxysteroid dehydrogenase type 1 promoter activity in Leydig cells
-
additional information
-
3beta-HSD mRNA level significantly increases in Leydig cells of corticosterone-deficient rats and simultaneous corticosterone treatment completely maintains the expression at control levels
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0064
16alpha-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD1, pH 7.4, 27°C
0.0148
16alpha-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD2, pH 7.4, 27°C
0.0014
16beta-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD1, pH 7.4, 27°C
0.0184
16beta-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD2, pH 7.4, 27°C
0.0037
dehydroepiandrosterone
27°C, pH 7.4; pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD1
0.0037
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD1
0.0044
dehydroepiandrosterone
-
mutant C72S, presence of 2-mercatoethanol pH 7.4
0.0061
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q240R
0.0075
dehydroepiandrosterone
-
mutant C83A, presence of 2-mercatoethanol pH 7.4
0.0115
dehydroepiandrosterone
-
mutant C72F, presence of 2-mercatoethanol pH 7.4
0.0168
dehydroepiandrosterone
-
mutant C111S, presence of 2-mercatoethanol pH 7.4
0.0237
dehydroepiandrosterone
-
mutant C111A, presence of 2-mercatoethanol pH 7.4
0.025
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant Q105M
0.0327
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant R240Q
0.0405
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q105M
0.042
dehydroepiandrosterone
27°C, pH 7.4, H156Y mutant 3beta-HSD1
0.0424
dehydroepiandrosterone
pH 7.4, 27°C, recombinant mutant H156Y; pH 7.4, 27°C, recombinant mutant H156Y
0.0473
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD2
0.0473
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD2
0.0256
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q240R
0.0341
NAD+
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD1
0.0372
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant R240Q
0.0388
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q105M
0.0614
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant Q105M
0.0863
NAD+
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD2
additional information
additional information
kinetics recombinant wild-type isozyme and mutant H165Y, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity; kinetics recombinant wild-type isozymes and mutant H165Y, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity
-
additional information
additional information
kinetics recombinant wild-type isozyme and mutant H165Y, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity; kinetics recombinant wild-type isozymes and mutant H165Y, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity
-
additional information
additional information
kinetics, recombinant wild-type and mutant isozymes, overview, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity; kinetics, recombinant wild-type and mutant isozymes, overview, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity
-
additional information
additional information
kinetics, recombinant wild-type and mutant isozymes, overview, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity; kinetics, recombinant wild-type and mutant isozymes, overview, kinetics for the DELTA-5-3-ketosteroid isomerase, EC 5.3.3.1, activity
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.09
16alpha-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD1, pH 7.4, 27°C
0.15
16alpha-hydroxy-dehydroepiandrosterone
-
mutant R195P, pH 7.4, 27°C; wild-type 3beta-HSD2, pH 7.4, 27°C
0.023
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q240R
0.047
dehydroepiandrosterone
-
mutant C111A, presence of 2-mercatoethanol pH 7.4
0.055
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD1
0.062
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD1
0.075
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant Q105M
0.087
dehydroepiandrosterone
-
mutant C72F, pH 7.4; mutant C72F, presence of 2-mercatoethanol pH 7.4
0.113
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q105M
0.115
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD2
0.118
dehydroepiandrosterone
pH 7.4, 27°C, recombinant wild-type isozyme 3beta-HSD2
0.12
dehydroepiandrosterone
27°C, pH 7.4; 27°C, pH 7.4, H156Y mutant 3beta-HSD1; pH 7.4, 27°C, recombinant mutant H156Y; pH 7.4, 27°C, recombinant mutant H156Y
0.217
dehydroepiandrosterone
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant R240Q
0.022
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q240R
0.038
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD1 mutant Q105M
0.087
NAD+
-
mutant C72F, pH 7.4; mutant C72F, presence of 2-mercatoethanol pH 7.4
0.145
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant Q105M
0.187
NAD+
pH 7.4, 27°C, recombinant isozyme 3beta-HSD2 mutant R240Q
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
10.16
16alpha-hydroxy-dehydroepiandrosterone
-
wild-type 3beta-HSD2, pH 7.4, 27°C
0.0028
dehydroepiandrosterone
mutant H156Y, pH 7.4, 27°C; mutant Q105M, pH 7.4, 27°C
0.012
dehydroepiandrosterone
mutant P195R, pH 7.4, 27°C; mutant R195P, pH 7.4, 27°C
7.33
dehydroepiandrosterone
-
mutant E192A, pH 7.4, 27°C; wild-type 3beta-HSD2, pH 7.4, 27°C