Information on EC 1.1.1.51 - 3(or 17)beta-hydroxysteroid dehydrogenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
1.1.1.51
-
RECOMMENDED NAME
GeneOntology No.
3(or 17)beta-hydroxysteroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD(P)+ = androstenedione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
oxidation
-
-
redox reaction
-
-
-
-
redox reaction
-
-
reduction
-
-
-
-
reduction
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen and estrogen metabolism
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
Steroid degradation
-
-
Steroid hormone biosynthesis
-
-
testosterone and androsterone degradation to androstendione
-
-
SYSTEMATIC NAME
IUBMB Comments
3(or 17)beta-hydroxysteroid:NAD(P)+ oxidoreductase
Also acts on other 3beta- or 17beta-hydroxysteroids. cf. EC 1.1.1.209 3(or 17)alpha-hydroxysteroid dehydrogenase.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
17 beta-hydroxysteroid dehydrogenase
-
-
17-beta-HSD
-
-
17-ketoreductase
-
-
-
-
17beta-HSD
-
-
17beta-HSD
-
-
17beta-HSD
-
-
17beta-HSD (type 1)
-
-
17beta-HSD (type 3)
-
-
17beta-HSD type 3
Q6QA32
-
17beta-HSD type 3
-
-
17beta-HSD type II
-
-
17beta-HSD-3
-
-
17beta-HSD2
-
-
17beta-HSD3
-
-
17beta-HSD3
P37058
-
17beta-HSD5
-
-
17beta-HSD7_2
-
-
17beta-HSOR
-
-
17beta-hydroxy steroid dehydrogenase
-
-
-
-
17beta-hydroxysteroid dehydrogenase
-
-
17beta-hydroxysteroid dehydrogenase
-
-
17beta-hydroxysteroid dehydrogenase 2
-
-
17beta-hydroxysteroid dehydrogenase type 3
Q6QA32
-
17beta-hydroxysteroid dehydrogenase type 3
-
-
17beta-hydroxysteroid dehydrogenase type 3
P37058
-
17beta-hydroxysteroid dehydrogenase type 3
-
-
17beta-hydroxysteroid dehydrogenases type 2
-
-
17beta-hydroxysteroid oxidoreductase
-
-
17betaHSD2
-
-
3 beta-hydroxysteroid dehydrogenase
-
-
3-beta HSD
-
-
3beta,17beta-hydroxysteroid dehydrogenase
-
-
-
-
3beta-HSD
-
-
3beta-HSD
Q7ZZC3
-
3beta-HSD
Q93Y47
-
3beta-HSD
Digitalis lanata EHRH
Q93Y47
-
-
3beta-HSD
-
-
3beta-HSD (type 1)
-
-
3beta-HSD type-I
B9UN12
isoform
3beta-HSD type-II
B9UN14
isoform
3beta-HSD/isomerase
-
-
3beta-HSD/isomerase
Aspergillus tamarii KITA
-
-
-
3beta-HSD/isomerase
-
-
3beta-hydroxy steroid dehydrogenase
-
-
-
-
3beta-hydroxy-steroid dehydrogenase/DELTA5-DELTA4 isomerase
-
-
3beta-hydroxy-steroid dehydrogenase/DELTA5-DELTA4 isomerase
Aspergillus tamarii KITA
-
-
-
3beta-hydroxysteroid dehydrogenase
-
-
-
-
3beta-hydroxysteroid dehydrogenase
Q7ZZC3
-
3beta-hydroxysteroid dehydrogenase
Q93Y47
-
3beta-hydroxysteroid dehydrogenase
Digitalis lanata EHRH
Q93Y47
-
-
3beta-hydroxysteroid dehydrogenase
-
-
3beta-hydroxysteroid dehydrogenase
-
-
3beta-hydroxysteroid dehydrogenase
-
-
3beta-hydroxysteroid dehydrogenase/DELTA5-4-isomerase
-
-
3beta-hydroxysteroid dehydrogenase/DELTA5-DELTA4-isomerase
-
-
3beta-hydroxysteroid dehydrogenase/isomerase
B9UN12, B9UN14
-
3beta-hydroxysteroid dehydrogenase/isomerase
-
-
3beta-hydroxystroid oxidoreductase
-
-
-
-
3beta/17beta-hydroxysteroid dehydrogenase
-
-
3beta17betaHSDH
-
-
-
-
3betaHSD
Q93Y47
-
3betaHSD
-
-
beta-hydroxy steroid dehydrogenase
-
-
-
-
dehydrogenase, 17beta-hydroxy steroid
-
-
-
-
dehydrogenase, 3beta-hydroxy steroid
-
-
-
-
dehydrogenase, beta-hydroxy steroid
-
-
-
-
DELTA5-3beta-HSD
-
-
DELTA5-3beta-HSD
Rattus norvegicus Wistar
-
-
-
DELTA5-3beta-hydroxysteroid dehydrogenase
Q93Y47
-
DELTA5-3beta-hydroxysteroid dehydrogenase
-
-
form 2 type 7 17beta-hydroxysteroid dehydrogenase
-
-
pQ3 beta HSD
Q93Y47
-
steroid 17beta-reductase
-
-
-
-
type 17beta-HSD
-
-
type 2 17beta-HSD
-
-
type 3 17beta-HSD
-
-
type 3 17beta-hydroxysteroid dehydrogenase
-
-
additional information
-
the enzyme is a member of the short-chain dehydrogenase/reductase, SDR, superfamily
additional information
-
the enzyme belongs to the short-chain alcohol dehydrogenase family
additional information
-
cf. 1.1.1.62
CAS REGISTRY NUMBER
COMMENTARY
9015-81-0
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain KITA
-
-
Manually annotated by BRENDA team
Aspergillus tamarii KITA
strain KITA
-
-
Manually annotated by BRENDA team
female
-
-
Manually annotated by BRENDA team
Clostridium innocuum
-
-
-
Manually annotated by BRENDA team
Comamonas testosteroni ATTC 11996
ATTC 11996
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
Manually annotated by BRENDA team
female (C3H/HeJ 129/J)F1 (C31) hybrid mice
-
-
Manually annotated by BRENDA team
Nile tilapia, tissue-specific isozymes 17beta-HSD1 and 17beta-HSD8
-
-
Manually annotated by BRENDA team
ten 10-week-old Sprague-Dawley
-
-
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
Rattus norvegicus Wistar
Wistar
-
-
Manually annotated by BRENDA team
Landrace piglet
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
key enzyme in cardenolide biosynthesis
physiological function
Digitalis lanata EHRH
-
key enzyme in cardenolide biosynthesis
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
show the reaction diagram
-
i.e. 11beta-hydroxy-androstenedione, reduction at C17
i.e. 11beta-testosterone
-
?
11beta-hydroxyandrost-5-ene-3,17-dione + NADPH
11beta,17beta-dihydroxyandrost-5-ene-3-one + NADP+
show the reaction diagram
Q6QA32
i.e. 11beta-hydroxy-androstenedione, reduction at C17
i.e. 11beta-testosterone
-
?
17-oxo steroids + NADPH
?
show the reaction diagram
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
-
17alpha-hydroxypregnenolone + NAD(P)+
17alpha-hydroxy-pregn-5-en-3,20-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
17beta-hydroxy-5beta-androstane-3-one + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
B9UN12, B9UN14
-
-
-
?
20alpha-dihydroprogesterone + NAD+
4-pregnen-3alpha,20beta-diol + NADH
show the reaction diagram
-
-
-
-
r
20alpha-dihydroprogesterone + NADP+
4-pregnen-3alpha,20beta-diol + NADPH
show the reaction diagram
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + NADP+
progesterone + NADPH
show the reaction diagram
-
-
-
r
3beta-hydroxy-16alpha,17alpha-epoxypregn-5-en-20-one + NAD(P)+
?
show the reaction diagram
Aspergillus tamarii, Aspergillus tamarii KITA
-
-
-
-
?
3beta-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
-
-
-
?
4-androsten-17beta-ol-3-one + NAD(P)+
4-androstene-3,17-dione + NAD(P)H + H+
show the reaction diagram
Q93Y47
17keto function is reduced. NADP+ is 3-5times less effective than NAD+
-
-
?
4-androsten-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
P37058
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
r
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
selective reduction at C17
-
-
?
4-estrene-17beta-ol-3-one + NADP+
4-estrene-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
4-estrene-3,17-dione + NADPH
4-estrene-17beta-ol-3-one + NADP+
show the reaction diagram
-
-
-
-
r
5-androsten-3beta-ol-17-one + NAD(P)+
5-androstene-3,17-dione + NAD(P)H + H+
show the reaction diagram
Q93Y47
NADP+ is 3-5times less effective than NAD+
-
-
?
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
isozyme 17beta-HSD3
-
-
r
5-pregnen-3beta-ol-20-one + NAD(P)+
5-pregnene-3,20-dione + NAD(P)H + H+
show the reaction diagram
Q93Y47
NADP+ is 3-5times less effective than NAD+
-
-
?
5alpha-androst-16-en-3-one + NADH
3beta-hydroxy-5alpha-androst-16-ene + NAD+
show the reaction diagram
-
-
-
?
5alpha-androstane-3beta,17beta-diol + NADP+
3beta-hydroxy-5alpha-androstan-17-one + NADPH
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
Rattus norvegicus, Rattus norvegicus Wistar
-
-
-
?
5alpha-pregnan-3beta-ol-20-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
show the reaction diagram
Q93Y47
NADP+ and NADPH are 3-5times less effective than NAD+ and NADH
-
-
r
5beta-pregnan-3,20-dione + NAD(P)H + H+
3beta-hydroxy-5beta-pregnan-20-one + NAD(P)+
show the reaction diagram
Q93Y47
NADP+ is 3-5times less effective than NAD+
-
-
?
5beta-pregnan-3,20-dione + NADH
3beta-hydroxy-5beta-pregnan-20-one + NAD+
show the reaction diagram
Clostridium innocuum
-
-
-
?
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
show the reaction diagram
Digitalis lanata, Digitalis lanata EHRH
-
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD(P)+
5-pregnan-3,20-dione + NAD(P)H + H+
show the reaction diagram
Q93Y47
NADP+ and NADPH are 3-5times less effective than NAD+ and NADH
-
-
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androst-5-ene-3,11,17-trione + NADPH
17beta-hydroxyandrost-5-ene-3,11-dione + NADP+
show the reaction diagram
Q6QA32
i.e. 11-keto-androstenedione, reduction at C17
i.e. 11-keto-testosterone
-
?
androst-5-ene-3,11,17-trione + NADPH
17beta-hydroxyandrost-5-ene-3,11-dione + NADP+
show the reaction diagram
-
i.e. 11-ketoandrostenedione, reduction at C17
i.e. 11-keto-testosterone
-
?
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
show the reaction diagram
-
-
-
r
androst-5-ene-3beta,17beta-diol + NADP+
dehydroepiandrosterone + NADPH
show the reaction diagram
Rattus norvegicus, Rattus norvegicus Wistar
-
-
-
r
androstane-3,17-dione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstanedione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
androstenediol + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
reaction catalysed by 3beta-HSD (type 1)
-
-
?
androstenedione + NAD(P)H + H+
testosterone + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
Q6QA32
-
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
the equilibrium state is 2% testosterone to 95% androstenedione
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
isozymes 17beta-HSD1 and 17beta-HSD8
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
the forward reaction is preferred, no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
Q6QA32
the forward reaction is preferred, no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
-
r
androsterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
Rattus norvegicus, Rattus norvegicus Wistar
-
-
-
?
androsterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NAD(P)+
androst-5-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
Aspergillus tamarii, Aspergillus tamarii KITA
-
-
-
-
?
dehydroepiandrosterone + NAD(P)H + H+
androstenediol + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
dehydroepiandrosterone + NAD+
4-androstene-3,17-dione + NADH + H+
show the reaction diagram
Homo sapiens, Rattus norvegicus, Rattus norvegicus Wistar
-
-
-
-
?
dehydroepiandrosterone + NAD+
androstene-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADPH
5-androstene-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH
androstene-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH
androstene-3beta,17beta-diol + NADP+
show the reaction diagram
Q6QA32
reduction at C17
-
-
?
dehydroepiandrosterone + NADPH + H+
androst-5-ene-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
dihydroepiandrostendione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
dihydrotestosterone + NAD+
5alpha-androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
-
r
dihydrotestosterone + NADP+
5alpha-androstan-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
androsterone inactivation
-
-
?
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
Q6QA32
reduction at C17
-
-
?
epiandrosterone + NADPH
5-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
estradiol + NAD(P)+
estrone + NAD(P)H
show the reaction diagram
-
-
-
-
?
estradiol + NAD+
estrone + NADH
show the reaction diagram
-
-
-
-
?
estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
-
?
estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
r
estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
-
-
r
estradiol + NADP+
estrone + NADPH
show the reaction diagram
-
the equilibrium state is 3% estradiol and 97% estrone
-
-
r
estradiol + NADP+
estrone + NADPH
show the reaction diagram
Rattus norvegicus Wistar
-
-
-
r
estradiol sulfate + NADP+
estrone sulfate + NADPH
show the reaction diagram
-
-
-
?
estrone + NAD(P)H + H+
estradiol + NAD(P)+
show the reaction diagram
-
reaction catalysed by 17beta-HSD (type 1 and 3)
-
-
?
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
show the reaction diagram
B9UN12, B9UN14
-
-
-
?
pregnenolone + NAD(P)+
progesterone + NAD(P)H + H+
show the reaction diagram
Aspergillus tamarii KITA
-
-
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
-
the mitochondrial enzyme is essential for the synthesis of progesterone by corpora lutea, overview
-
-
?
pregnenolone + NADP+
progesterone + NADPH + H+
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH
progesterone + NADP+
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + H+
isoprogesterone + NADP+
show the reaction diagram
Digitalis lanata, Digitalis lanata EHRH
-
-
-
-
?
testosterone + 3-acetylpyridine adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
testosterone + 3-pyridinealdehyde adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
r
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
r
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
r
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
Rattus norvegicus Wistar
-
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
Rattus norvegicus Wistar
-
-
-
?
testosterone + NAD+
androst-4-en-3,17-dione + NADH
show the reaction diagram
-
-
-
-
r
testosterone + NADP+
androst-4-en-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
testosterone + thionicotinamide adenine dinucleotide
?
show the reaction diagram
-
-
-
-
?
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
additional information
?
-
-
activity of the enzyme is associated with the mechanism of prostatic regulation by androgens after castration, which is important in prostate cancer
-
-
-
additional information
?
-
-
evolutionary considerations
-
-
-
additional information
?
-
Q6QA32
evolutionary considerations
-
-
-
additional information
?
-
-
the enzyme is an important therapeutic target for androgen-sensitive diseases, overview
-
-
-
additional information
?
-
-
the enzyme plays a role in gonadal steroidogenesis
-
-
-
additional information
?
-
-
the isozyme 17beta-HSD3 is a critical determinant in steroid hormone biosynthesis
-
-
-
additional information
?
-
-
the isozyme might play an imporant role in modulation of active hormone levels in estrogen-sensitive cells or tissues
-
-
-
additional information
?
-
-
isozyme 17beta-HSD5 also shows 3alpha- and 20alpha-hydroxysteroid dehydrogenase, dihydrodiol dehydrogenase, and prostaglandin synthase activities
-
-
-
additional information
?
-
Q6QA32
no activity with androstanedione and androsterone
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17-oxo steroids + NADPH
?
show the reaction diagram
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
-
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
isozymes 17beta-HSD3 and 17beta-HSD5
-
-
r
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
isozyme 17beta-HSD3
-
-
r
5beta-pregnan-3,20-dione + NADPH + H+
5beta-pregnane-3beta-ol-20-one + NADP+
show the reaction diagram
Digitalis lanata, Digitalis lanata EHRH
-
-
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstane-3,17-dione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
r
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
Q6QA32
-
-
-
r
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
androsterone inactivation
-
-
?
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
-
the mitochondrial enzyme is essential for the synthesis of progesterone by corpora lutea, overview
-
-
?
pregnenolone + NADPH + H+
isoprogesterone + NADP+
show the reaction diagram
Digitalis lanata, Digitalis lanata EHRH
-
-
-
-
?
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
additional information
?
-
-
activity of the enzyme is associated with the mechanism of prostatic regulation by androgens after castration, which is important in prostate cancer
-
-
-
additional information
?
-
-
evolutionary considerations
-
-
-
additional information
?
-
Q6QA32
evolutionary considerations
-
-
-
additional information
?
-
-
the enzyme is an important therapeutic target for androgen-sensitive diseases, overview
-
-
-
additional information
?
-
-
the enzyme plays a role in gonadal steroidogenesis
-
-
-
additional information
?
-
-
the isozyme 17beta-HSD3 is a critical determinant in steroid hormone biosynthesis
-
-
-
additional information
?
-
-
the isozyme might play an imporant role in modulation of active hormone levels in estrogen-sensitive cells or tissues
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3-acetylpyridine adenine dinucleotide
-
-
NAD(P)H
B9UN12, B9UN14
;
NAD+
-
-
NAD+
-
-
NAD+
-
prefers NAD+ over NADP+
NAD+
-
-
NADH
-
-
NADH
Clostridium innocuum
-
-
NADP+
-
specific for
NADP+
-
prefers NAD+ over NADP+
NADP+
Q6QA32
-
NADPH
-
specific for
NADPH
Q6QA32
-
NADPH
-
binding of the coenzyme NADPH to the enzyme causes local structural changes that do not significantly affect the thermal stability of this protein
NADPH
-
dependent on
3-pyridinealdehyde adenine dinucleotide
-
-
additional information
Clostridium innocuum
-
-
-
additional information
Q6QA32
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
additional information
-
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
NaCl
-
addition of a neutral electrolyte, such as NaCl, shields repulsion interactions in the highly positively charged enzyme at pH 2.0, effects on the secondary structure by increasing NaCl concentrations at pH 2.0 and 25C, overview
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2,4-dihydroxyphenyl)-phenylmethanone
P37058
remaining 17beta HSD3 activity: 1.1%
(2,4-dihydroxyphenyl)-phenylmethanone
-
(2,4-dihydroxyphenyl)-phenylmethanone leads to inhibition of testosterone synthesis in freshly isolated mouse and rat testis tissue
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
-
IC50: 0.00297 mM
1-(5,6,11,12-tetrahydrodibenzo[b,f]azocin-12-yl)ethanone
-
IC50: 0.00474 mM
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]ethanone
-
IC50: 0.02 nM
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
-
IC50: 0.00024 mM; IC50: 0.00029 mM
11-[3-hydroxy-17-beta-hydroxyestr-5(10)-en-17alpha-yl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-undecanoic acid butyl-methyl-amide
-
selective inhibition of type 2 17beta-HSD
12-acetyl-1-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0115 mM
12-acetyl-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
P37058
-
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
P37058
-
12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocin-3-ol
-
IC50: 0.0049 mM
12-acetyl-2,3-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00001 mM
12-acetyl-2-(trifluoromethyl)-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00281 mM
12-acetyl-2-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00003 mM
12-acetyl-3,4-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00076 mM
12-acetyl-3-bromo-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00025 mM
12-acetyl-3-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00010 mM
12-acetyl-3-fluoro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00009 mM
12-acetyl-3-methoxy-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0021 mM
12-acetyl-3-methyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.001 mM
13-cis-retinoic acid
-
-
17-hydroxy-7alpha-thioethyl-3-oxo-4-androstene-17alpha-propionic acid, gamma-lactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0009 mM
17alpha-ethynyl-estradiol
-
0.01 mM, 54% inhibition, reaction with 0.002 mM estradiol; inhibits oxidation of testosterone
17beta-dihydroequilin
-
0.01 mM, 88% inhibition, reaction with 0.002 mM estradiol
2,2',4,4'-tetrahydroxybenzophenone
P37058
remaining 17beta HSD3 activity: 47%
2,5-dioxo-3-(2-propyn-1-yl)-3-pyrrolidinecarboxylic acid 2,3,3-triphenyl-2-propen-1-yl-ester
P37058
-
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
P37058
-
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo(b,f)azocin-8-yl)-benzoic acid methyl ester
P37058
-
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
2-hydroxy-estradiol
-
0.01 mM, 67% inhibition, reaction with 0.002 mM estradiol
20alpha-dihydroprogesterone
-
0.01 mM, 71% inhibition, reaction with 0.002 mM estradiol, inhibits oxidation of testosterone
3,4-dihydrobenzoic acid
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
3-benzylidene camphor
P37058
remaining 17beta HSD3 activity: 56%
3-hydroxy-1,3,5(10)-estratriene-17beta-O,17alpha-butanolactone
-
selective for type 2 17beta-HSD versus types 1, 3, and 7 but not versus type 5 17beta-HSD
3-oxo-17alpha-pregna-4-ene-7alpha-(benzylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.00042 mM,IC50 for oxidation of testosterone: 0.001 mM
3-oxo-17alpha-pregna-4-ene-7alpha-(phenylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.001 mM
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0011 mM; IC50 for reduction of androst-4-en-3,17-dione: 0.0014 mM
3-oxo-17alpha-pregna-4-ene-7alpha-[4-[2-(1-piperidinyl)-ethoxy]benzylthia]-21,17-carbolactone
-
IC50 for oxidation of testosterone: 0.0007 mM, no inhibition of type 1, 3 and 5 17beta-HSD, nor against P450 aromatase
3alpha-alkylated androsterone derivatives
-
17-88% inhibition at 0.003 mM, overview
-
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
P37058
-
3alpha-ether-3beta-substituted androsterone derivatives
-
diverse derivatives, IC50: 70-760 nM, overview
-
3beta-alkylated androsterone derivatives
-
IC50: 57-147 nM
-
3beta-cyclohexylethyl-androsterone
-
-
3beta-hexyl-androsterone
-
-
3beta-phenyl-androsterone
-
mixed-type inhibition, shows some proliferative activity on AR+ and Er+ cell lines not mediated through androgen or estrogen receptors
3beta-phenylethyl-3alpha-methyl-O-androsterone
-
IC50: 73 nM
3beta-phenylethyl-androsterone
-
IC50: 99 nM
3beta-phenylethyl-androsterone
-
-
3beta-phenylmethyl-androsterone
-
IC50: 57 nM
3beta-phenylmethyl-androsterone
-
mixed-type inhibition, shows some proliferative activity on AR+ and Er+ cell lines not mediated through androgen or estrogen receptors
3beta-substituted androsterone derivatives
-
IC50: 57-147 nM
-
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)-N-methylbenzamide
-
IC50: 25 nM
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 5 nM
4-MA
-
-
4-methylbenzylidene camphor
P37058
remaining 17beta HSD3 activity: 33%
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00007 mM
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
P37058
-
5-acetyl-2-chloro-5,6-dihydrodibenzo[b,f]azocine
-
IC50: 0.00024 mM
5-acetyl-2-chloro-8-(2-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 3 nM
5-acetyl-2-chloro-8-(3-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 8 nM
5-acetyl-2-chloro-8-(4-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 2 nM
5-acetyl-2-chloro-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 4 nM
5-acetyl-3-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00005 mM
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
P37058
-
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 0.00049 mM
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine-9-carboxamide
-
IC50: 0.001 mM
5-acetyl-8-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 9 nM
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.02 nM
5-acetyl-9-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 7 nM
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 8 nM
5alpha-androstane-3alpha,17beta-diol
-
0.01 mM, 87% inhibition, reaction with 0.002 mM estradiol
5alpha-dihydrotestosterone
-
inhibits oxidation of testosterone
5beta-androstane-3alpha,17beta-diol
-
0.01 mM, 83% inhibition, reaction with 0.002 mM estradiol
5beta-dihydrotestosterone
-
inhibits oxidation of testosterone
9-bromo-11,12-dihydrodibenzo[b,f]azocine-5(6H)-carboxamide
-
IC50: 0.00028 mM
9-bromo-5-butanoyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00032 mM
9-bromo-5-ethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.001 mM
9-cis-retinoic acid
-
weak
9-cis-retinoic acid
-
-
Albumin
-
-
-
androsterone
P37058
-
beta-octylglucoside
-
strong
chloromercuribenzene-p-sulfonic acid
-
-
cyproterone acetate
-
-
danazol
-
inhibits oxidation of testosterone, 0.01 mM, 83% inhibition
dibenzothiazocine
-
IC50: 0.0004 mM
Dimethylsulfoxide
-
-
Dodecyl-beta-D-maltoside
-
inhibition above 0.5%
epostane
-
-
estradiol
-
inhibits oxidation of testosterone
gallic acid
-
0.001 mM, 50% inhibition, reduction of androst-4-en-3,17-dione
glycerol
-
-
Iodosobenzoate
-
-
methyl 12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine-3-sulfinate
-
IC50: 0.01 mM
methyl 3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM; IC50: 0.7 nM
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 0.00014 mM
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
P37058
-
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
-
IC50: 0.00016 mM
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
-
Perfluorooctanoic acid
-
-
Propyleneglycol
-
-
spiro-gamma-lactone-estradiol
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
spironolactone
-
IC50 for oxidation of testosterone: 0.0011 mM
Strogen forte
-
standardized extract of the plant Sabalis serrulata, 0.212 mg/ml result in 50% enzyme inhibition
-
Strogen forte
-
standardized extract of the plant Sabalis serrulata, 0.4 mg/ml result in 50% enzyme inhibition
-
testosterone
-
0.01 mM, 70% inhibition, reaction with 0.002 mM estradiol
tetrahydrodibenzazocine
-
IC50: 0.00009 mM
Triton X-100
-
-
Triton X-100
-
significant
Tween-80
-
-
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 2 nM
additional information
-
synthesis, inhibitory potency, and in vivo effects of the diverse inhibitor derivatives, detailed overview
-
additional information
-
design, synthesis and in vitro evaluation of 4-androstene-3,17-dione/adenosine hybrid compounds as bisubstrate inhibitors of type 3 17beta-HSD, the bisubstrate inhibitors are less potent in intact cells than in homogenated cells, overview, the best inhibitors of that series are those bearing an alkyl side-chain spacer of 11 or 12 methylenes with inhibition of 69% and 78% at 1 mM
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00053
20alpha-dihydroprogesterone
-
pH 7.4, with NAD+ as cofactor
0.685
3-acetylpyridine adenine dinucleotide
-
testosterone as substrate
0.063
3-pyridinealdehyde adenine dinucleotide
-
testosterone as substrate
0.642
5-androsten-3beta-ol-17-one
-
50C, pH 7.8
0.09
5-pregnen-3beta-ol-20-one
-
50C, pH 7.8
0.068
5alpha-Androst-16-en-3-one
-
microsomal enzyme
0.107
5alpha-Androst-16-en-3-one
-
mitochondrial enzyme
0.176
5alpha-Androst-16-en-3-one
-
cytosolic enzyme
0.14
5alpha-dihydrotestosterone
-
-
0.2
5alpha-dihydrotestosterone
-
cofactor NAD+ or NADP+
0.106
5alpha-pregnan-3,20-dione
-
50C, pH 7.8
0.116
5alpha-pregnan-3beta-ol-20-one
-
50C, pH 7.8
0.21
5beta-pregnan-3,20-dione
Clostridium innocuum
-
-
1.725
5beta-pregnan-3,20-dione
-
50C, pH 7.8
0.314
5beta-Pregnan-3beta-ol-20-one
-
50C, pH 7.8
0.00001
dehydroepiandrosterone
-
37C, pH not specified in the publication
0.00025
dihydrotestosterone
-
pH 7.4, with NAD+ as cofactor
0.00035
estradiol
-
pH 7.4, with NAD+ as cofactor
0.083
NAD+
-
testosterone as substrate
0.11
NAD+
-
pH 7.4, reaction with estradiol
0.167
NAD+
-
pH 7.4, reaction with testosterone
0.26
NAD+
-
50C, pH 7.8
0.0053
NADH
-
pH 7.4, reaction with 4-dionetestosterone
0.0056
NADH
-
pH 7.4, reaction with estronel
0.642
NADH
-
50C, pH 7.8
0.0082
NADP+
-
testosterone as substrate, 17beta-hydroxysteroid dehydrogenase activity
0.009
NADP+
-
3beta-hydroxy-5alpha-androstan-17-one as substrate, 3beta-hydroxysteroid dehydrogenase activity
9.6
NADP+
-
pH 7.4, reaction with estradiol
0.0018
NADPH
-
5alpha-dihydrotestosterone as substrate, 3-beta-hydroxysteroid dehydrogenase activity
0.0021
NADPH
-
estrone as substrate, 17beta-hydroxysteroid dehydrogenase activity
0.00067
pregnenolone
-
pH and temperature not specified in the publication
0.00061
testosterone
-
pH 7.4, with NAD+ as cofactor
0.17
testosterone
-
-
0.2
testosterone
-
cofactor NAD+ or NADP+
0.23
testosterone
-
-
0.24
testosterone
-
NADP+ as variable substrate
0.31
testosterone
-
-
0.083
Thionicotinamide adenine dinucleotide
-
testosterone as substrate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.78
20alpha-dihydroprogesterone
-
pH 7.4, with NAD+ as cofactor
2.4
dihydrotestosterone
-
pH 7.4, with NAD+ as cofactor
3.9
estradiol
-
pH 7.4, with NAD+ as cofactor
2.9
NAD+
-
pH 7.4, reaction with testosterone
4.7
NAD+
-
pH 7.4, reaction with estradiol
0.27
NADH
-
pH 7.4, reaction with 4-dionetestosterone
0.33
NADH
-
pH 7.4, reaction with estronel
1.3
NADP+
-
pH 7.4, reaction with estradiol
3.4
testosterone
-
pH 7.4, with NAD+ as cofactor
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0024
13-cis-retinoic acid
-
-
0.0003
17alpha-ethynyl-estradiol
-
-
0.0041
9-cis-retinoic acid
-
-
0.0006
danazol
-
-
0.0008
estradiol
-
-
0.0153
Perfluorooctanoic acid
-
testicular microsome, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.0213
Perfluorooctanoic acid
-
testicular microsome, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.0586
Perfluorooctanoic acid
-
intact Leydig cells, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.181
Perfluorooctanoic acid
-
intact Leydig cells, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.001
(2,4-dihydroxyphenyl)-phenylmethanone
P37058
pH 7.4, 37C
0.00297
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
-
IC50: 0.00297 mM
0.00474
1-(5,6,11,12-tetrahydrodibenzo[b,f]azocin-12-yl)ethanone
-
IC50: 0.00474 mM
0.00000002
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]ethanone
-
IC50: 0.02 nM
0.00024
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
-
IC50: 0.00024 mM
0.00029
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
-
IC50: 0.00029 mM
0.0115
12-acetyl-1-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0115 mM
0.00281
12-acetyl-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
P37058
pH and temperature not specified in the publication
0.0004
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
P37058
pH and temperature not specified in the publication
0.0049
12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocin-3-ol
-
IC50: 0.0049 mM
0.00001
12-acetyl-2,3-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00001 mM
0.00281
12-acetyl-2-(trifluoromethyl)-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00281 mM
0.00003
12-acetyl-2-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00003 mM
0.00076
12-acetyl-3,4-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00076 mM
0.00025
12-acetyl-3-bromo-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00025 mM
0.0001
12-acetyl-3-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00010 mM
0.00009
12-acetyl-3-fluoro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.00009 mM
0.0021
12-acetyl-3-methoxy-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.0021 mM
0.001
12-acetyl-3-methyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
-
IC50: 0.001 mM
0.0009
17-hydroxy-7alpha-thioethyl-3-oxo-4-androstene-17alpha-propionic acid, gamma-lactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0009 mM
0.0181
2,2',4,4'-tetrahydroxybenzophenone
P37058
pH 7.4, 37C
0.00915
2,5-dioxo-3-(2-propyn-1-yl)-3-pyrrolidinecarboxylic acid 2,3,3-triphenyl-2-propen-1-yl-ester
P37058
pH and temperature not specified in the publication
0.00006
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
P37058
pH and temperature not specified in the publication
0.00000002
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo(b,f)azocin-8-yl)-benzoic acid methyl ester
P37058
pH and temperature not specified in the publication
0.000003
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
0.000003
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
0.033
3-benzylidene camphor
P37058
pH 7.4, 37C
0.001
3-oxo-17alpha-pregna-4-ene-7alpha-(benzylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.00042 mM,IC50 for oxidation of testosterone: 0.001 mM
0.001
3-oxo-17alpha-pregna-4-ene-7alpha-(phenylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.001 mM
0.0011
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0011 mM
0.0014
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0014 mM
0.0007
3-oxo-17alpha-pregna-4-ene-7alpha-[4-[2-(1-piperidinyl)-ethoxy]benzylthia]-21,17-carbolactone
-
IC50 for oxidation of testosterone: 0.0007 mM, no inhibition of type 1, 3 and 5 17beta-HSD, nor against P450 aromatase
0.000116
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
P37058
pH and temperature not specified in the publication
0.00007 - 0.00076
3alpha-ether-3beta-substituted androsterone derivatives
-
diverse derivatives, IC50: 70-760 nM, overview
-
0.000057 - 0.000147
3beta-alkylated androsterone derivatives
-
IC50: 57-147 nM
-
0.000073
3beta-phenylethyl-3alpha-methyl-O-androsterone
-
IC50: 73 nM
0.000099
3beta-phenylethyl-androsterone
-
IC50: 99 nM
0.000057
3beta-phenylmethyl-androsterone
-
IC50: 57 nM
0.000057 - 0.000147
3beta-substituted androsterone derivatives
-
IC50: 57-147 nM
-
0.000025
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)-N-methylbenzamide
-
IC50: 25 nM
0.000005
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 5 nM
0.00000145
4-MA
-
37C, pH not specified in the publication
0.0107
4-methylbenzylidene camphor
P37058
pH 7.4, 37C
0.00007
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00007 mM
0.00024
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
P37058
pH and temperature not specified in the publication
0.00024
5-acetyl-2-chloro-5,6-dihydrodibenzo[b,f]azocine
-
IC50: 0.00024 mM
0.000003
5-acetyl-2-chloro-8-(2-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 3 nM
0.000008
5-acetyl-2-chloro-8-(3-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 8 nM
0.000002
5-acetyl-2-chloro-8-(4-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 2 nM
0.000004
5-acetyl-2-chloro-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 4 nM
0.00005
5-acetyl-3-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00005 mM
0.00474
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
P37058
pH and temperature not specified in the publication
0.00049
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 0.00049 mM
0.001
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine-9-carboxamide
-
IC50: 0.001 mM
0.000009
5-acetyl-8-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 9 nM
0.00000002
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.02 nM
0.000007
5-acetyl-9-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 7 nM
0.000008
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
-
IC50: 8 nM
0.00028
9-bromo-11,12-dihydrodibenzo[b,f]azocine-5(6H)-carboxamide
-
IC50: 0.00028 mM
0.00032
9-bromo-5-butanoyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00032 mM
0.001
9-bromo-5-ethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.001 mM
0.000182
androsterone
P37058
pH and temperature not specified in the publication
0.00015
cyproterone acetate
-
37C, pH not specified in the publication
0.0004
dibenzothiazocine
-
IC50: 0.0004 mM
0.0000062
epostane
-
37C, pH not specified in the publication
0.01
methyl 12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine-3-sulfinate
-
IC50: 0.01 mM
0.00004
methyl 3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM
0.0000007
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.7 nM
0.00004
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
-
IC50: 0.00004 mM
0.00014
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 0.00014 mM
0.000002
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 2 nM
0.000035
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
P37058
pH and temperature not specified in the publication
0.00016
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
-
IC50: 0.00016 mM
0.0177
Perfluorooctanoic acid
-
testicular microsome, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.0532
Perfluorooctanoic acid
-
testicular microsome, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.146
Perfluorooctanoic acid
-
intact Leydig cells, pH and temperature not specified in the publication, inhibition of 3beta-hydroxysteroid dehydrogenase
0.194
Perfluorooctanoic acid
-
intact Leydig cells, inhibition of 17beta-hydroxysteroid dehydrogenase, pH and temperature not specified in the publication
0.00025
spiro-gamma-lactone-estradiol
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
0.0011
spironolactone
-
IC50 for oxidation of testosterone: 0.0011 mM
0.00009
tetrahydrodibenzazocine
-
IC50: 0.00009 mM
0.0000009
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000000002255
-
male, 24 hours old, 37C, pH not specified in the publication
0.0000000003795
-
female, 24 hours old, 37C, pH not specified in the publication
0.000000000483
-
female, 48 hours old, 37C, pH not specified in the publication
0.000000000499
-
male, 48 hours old, 37C, pH not specified in the publication
0.000000001085
-
female, 0 hours old, 37C, pH not specified in the publication
0.000000002165
-
male, 0 hours old, 37C, pH not specified in the publication
0.00000000935
-
female abdominal skin, mean value, n=4, 37C, pH not specified in the publication
0.0000000122
-
male inguinal skin, mean value, n=8, 37C, pH not specified in the publication
0.0000000213
-
female perineal skin, mean value, n=4, 37C, pH not specified in the publication
additional information
-
-
additional information
-
determination of serum and tumor tissue concentrations of steroids in prostate cancer patients, overview
additional information
-
-
additional information
-
activities of the two key enzymes for testosterone biosynthesis, 3-beta-HSD and 17-beta-HSD, are significantly affected by rats subjected to semi-synthetic diet. Both enzyme activities are significantly decreased in interstitial cell homogenates from rats fed with a soybean diet and a grape seed diet compared with the levels observed in the group fed a olive or coconut diet
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 7
-
reductase activity
6 - 7.5
Clostridium innocuum
-
-
7.4
-
assay at
7.4
P37058
assay at
7.4
-
assay at
7.4
-
assay at
8.2
-
dehydrogenase activity
8.5
-
20 mM Tris-HCl
8.7
-
testosterone oxidation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
-
assay at
37
-
assay at
37
P37058
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
-
isoelectric focusing, pH-range: 3-9
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
derived from an epidermoid carcinoma of the vulva
Manually annotated by BRENDA team
-
isozyme 17beta-HSD5
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
Digitalis lanata EHRH
-
-
-
Manually annotated by BRENDA team
Q7ZZC3
exposure of the fish to water-soluble fraction of crude oil produces an apparent concentration-specific increase of 3beta-hydroxysteroid dehydrogenase
Manually annotated by BRENDA team
Q6QA32
enzyme expression during embryogenesis from sphere to 84 h post-fertilization
Manually annotated by BRENDA team
-
EpiskinTM is a cultured human epidermis. 17beta-hydroxysteroid dehydrogenase and 3alpha-hydroxysteroid dehdyrogenase activities are present at moderate levels in EpiskinTM, while 3beta-hydroxysteroid dehdyrogenase activity is low
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
isozymes 17beta-HSD3 and 17beta-HSD5
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
low expression level
Manually annotated by BRENDA team
-
low enzyme expression level
Manually annotated by BRENDA team
-
the relative expression level of 17beta- or 3beta-hydroxysteroid dehydrogenase is approximately 1.3-1.5fold higher at the neonatal than at the adult stage
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
Digitalis lanata EHRH
-
-
-
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
Digitalis lanata EHRH
-
-
-
Manually annotated by BRENDA team
-
3beta- and 17beta-hydroxysteroid dehydrogenase are not altered in metyrapone-treated cells
Manually annotated by BRENDA team
Q6QA32
highest enzyme expression in male liver
Manually annotated by BRENDA team
-
isozyme 17beta-HSD5
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
male pigs with high androstenone concentrations in fat have low 3betaHSD gene expression in liver and testis. Immunocastrated and surgically castrated male pigs shows significant increase of 3betaHSD expression. Fat androstenone is negatively correlated with liver 3betaHSD gene expression. The mRNA expression is generally much greater from the 3betaHSD than from the 17betaHSD gene
Manually annotated by BRENDA team
-
isozyme 17beta-HSD8
Manually annotated by BRENDA team
-
cultured muscle cell
Manually annotated by BRENDA team
Q6QA32
highest enzyme expression in female ovaries
Manually annotated by BRENDA team
-
isozyme 17beta-HSD1, predominantly
Manually annotated by BRENDA team
-
cancer and bening hyperplasia, protstaic intraepithelial neoplasia, enzyme distribution, overview
Manually annotated by BRENDA team
-
isozyme 17beta-HSD5
Manually annotated by BRENDA team
-
almost exclusively
Manually annotated by BRENDA team
-
high expression level of isozyme 17beta-HSD5
Manually annotated by BRENDA team
-
male pigs with high androstenone concentrations in fat have low 3betaHSD gene expression in liver and testis. Immunocastrated and surgically castrated male pigs shows significant increase of 3betaHSD expression. The mRNA expression is generally much greater from the 3betaHSD than from the 17betaHSD gene
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
-
taken from 10-20 days pregnant mice for enzyme extraction including the embryo
Manually annotated by BRENDA team
additional information
Q6QA32
expression in female and male tissues, sexual dimorphism, no activity in zf4 cells
Manually annotated by BRENDA team
additional information
-
three tissue-specific isozymes, 17beta-HSD1 and 17beta-HSD8
Manually annotated by BRENDA team
additional information
-
no actiovity in Sertoli cells
Manually annotated by BRENDA team
additional information
-
the enzyme is also expressed in cardenolide-free tissues of cardenolide-containing plants
Manually annotated by BRENDA team
additional information
Digitalis lanata EHRH
-
the enzyme is also expressed in cardenolide-free tissues of cardenolide-containing plants
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Clostridium innocuum
-
-
Manually annotated by BRENDA team
-
80% of activity
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
-
the hydrophobic 17beta-HSD3 is membrane-bound through an N-terminal transmembrane domain
Manually annotated by BRENDA team
additional information
-
the enzyme is distributed between microsomes and mitochondria, the HSD activity in microsomes is predominant throughout the follicular phase of the estrous cycle, the enzyme activity is increased in pregnant mice uteri including embryos, overview
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
32000
-
gel filtration
287076
64000
-
gel filtration
287072
70000
-
gel filtration
287073
80000
Clostridium innocuum
-
gel filtration
287079
90400
-
glycerol gradient ultracentrifugation
659176
98500
-
native PAGE
287075
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 41475, amino acid sequence calculation
?
-
x * 28561, calculated from sequence
dimer
-
2 * 42300, SDS-PAGE
dimer
-
secondary structure analysis at 25C and different pH values
tetramer
-
A3B, 4 * 23500-26700, SDS-PAGE, nonidentical subunits, similar in size, different in charge
tetramer
P19871
the enzyme has nearly identical subunits that form a tetramer with 222 symmetry. The subunit consists of a monomer with a single-domain structure built around a seven-stranded beta-sheet flanked by six alpha-helices
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
vapor diffusion technique, crystallographic analysis at 1.2 A resolution reveals the enzyme to have nearly identical subunits that form a tetramer with 222 symmetry. The subunit consists of a monomer with a single-domain structure built around a seven-stranded beta-sheet flanked by six alpha-helices
P19871
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2
-
25C, 150300 mM NaCl, formation of soluble aggregates enriched in alpha-helical and beta-sheet structures, the soluble aggregates start to precipitate at higher temperatures and NaCl concentrations
673553
7 - 9
-
the native dimeric enzyme is thermally stable up to 40C in this pH range
673553
additional information
-
unstable under slightly alkaline conditions
287073
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
60
-
enzyme oligomers are resistant to temperatures up to 60C
673553
additional information
-
binding of the coenzyme NADPH to the enzyme causes local structural changes that do not significantly affect the thermal stability of this protein
673553
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
unfolding through 0.4 M guanidine hydrochloride
-
unfolding through 1.2 M urea
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimethylsulfoxide
-
3.3% v/v: inactivation 43%
dimethylsulfoxide
Rattus norvegicus Wistar
-
3.3% v/v: inactivation 43%
-
dioxane
-
3.3% v/v: inactivation 90%
dioxane
Rattus norvegicus Wistar
-
3.3% v/v: inactivation 90%
-
Ethanol
-
1.7% v/v: inactivation 22%
Ethanol
Rattus norvegicus Wistar
-
1.7% v/v: inactivation 22%
-
Glycerol
-
5% v/v: inactivation 26%
Glycerol
Rattus norvegicus Wistar
-
5% v/v: inactivation 26%
-
propyleneglycol
-
3.3% v/v: inactivation 50%
propyleneglycol
Rattus norvegicus Wistar
-
3.3% v/v: inactivation 50%
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, very labile in all extracts, inactivation in 5 days, but only 30% loss of activity if 20% glycerol is included
Clostridium innocuum
-
-20C, 5 mM potassium phosphate buffer, pH 7.5, 1 mM dithiothreitol, 50% glycerol, at least 7 months
-
-15C, a few percent loss of activity in several months
-
4C, activity in both the homogenate and the supernatant using dodecyl-beta-D-maltoside as detergent can be kept for several days without significant loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
His6-tagged 17beta-HSD2 overexpressed in Sf9 cells
-
partial
-
native enzyme partially from ovaries and pregnant uteri including embryos by subcellular fractionation of minced homogenates
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic analysis
-
DNA and amino acid sequence determination and analysis, phylogenetic tree, transient expression in zf4 cells
Q6QA32
cDNA is functionally expressed as a His-tagged fusion protein in Escherichia coli
-
gene 3bhsd, quantitative real-time PCR expression analysis
-
DNA and amino acid sequence determination and analysis, chromosome metaphase, interphase mapping, i.e. FISH mapping, localization on chromosome 10q11.2, stable expression in HEK-293 cells
-
DNA and amino acid sequence determination and analysis, phylogenetic tree, transient expression in HEK-293 cells
-
expressed in HEK-293 cells by transient transfection
P37058
His6-tagged 17beta-HSD2 overexpressed in Sf9 cells
-
overexpression in HEK-293 cells
-
overexpression of type 3 17beta-HSD in HEK-293 cells
-
expressed in HEK-293 cells by transient transfection
-
expressed in COS-7 cells; expressed in COS-7 cells
B9UN12, B9UN14
isozyme DNA and amino acid sequence determination and analysis, tissue-specific expression and phylogenetic analysis, expression of tissue-specific isozymes 17beta-HSD1 and 17beta-HSD8 in Escherichia coli and in HEK-293 cells
-
expressed in HEK-293 cells by transient transfection
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A231Y
-
mutation abolishes and decreases by 14.6fold the initial rates for steroid oxidation and reduction, respectively. Residue A231 allows the correct accommodation and conversion of steroids
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
-
inhibitor Strogen forte extract can be used for treatment of benign prostatic hyperplasia