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Information on EC 1.1.1.51 - 3(or 17)beta-hydroxysteroid dehydrogenase and Organism(s) Homo sapiens and UniProt Accession P37058

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EC Tree
IUBMB Comments
Also acts on other 3beta- or 17beta-hydroxysteroids. cf. EC 1.1.1.209 3(or 17)alpha-hydroxysteroid dehydrogenase.
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Select one or more organisms in this record: ?
This record set is specific for:
Homo sapiens
UNIPROT: P37058
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
3 beta-hydroxysteroid dehydrogenase, 17 beta-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase, hsd17b1, hsd17b3, 3betahsd, 17beta-hsd1, 17beta-hydroxysteroid dehydrogenases, 17beta-hydroxysteroid dehydrogenase type 1, 17beta-hsd3, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
17beta-hydroxysteroid dehydrogenase type 3
-
17-ketoreductase
-
-
-
-
17beta-HSD
-
-
17beta-HSD type 2
-
-
17beta-HSD type 3
-
-
17beta-HSD-3
-
-
17beta-HSD2
-
-
17beta-HSD3
-
-
17beta-HSD5
-
-
17beta-HSD7_2
-
-
17beta-HSOR
-
-
17beta-hydroxy steroid dehydrogenase
-
-
-
-
17beta-hydroxysteroid dehydrogenase
-
-
17beta-hydroxysteroid dehydrogenase 2
-
-
17beta-hydroxysteroid dehydrogenase type 1
-
17beta-hydroxysteroid dehydrogenase type 3
-
-
17beta-hydroxysteroid dehydrogenases type 2
-
-
17beta-hydroxysteroid oxidoreductase
-
-
17betaHSD2
-
-
3beta,17beta-hydroxysteroid dehydrogenase
-
-
-
-
3beta-HSD
-
-
3beta-hydroxy steroid dehydrogenase
-
-
-
-
3beta-hydroxysteroid dehydrogenase
3beta-hydroxysteroid dehydrogenase/DELTA5-4-isomerase
-
-
3beta-hydroxystroid oxidoreductase
-
-
-
-
3beta17betaHSDH
-
-
-
-
aldo keto reductase 1C3
-
beta-hydroxy steroid dehydrogenase
-
-
-
-
dehydrogenase, 17beta-hydroxy steroid
-
-
-
-
dehydrogenase, 3beta-hydroxy steroid
-
-
-
-
dehydrogenase, beta-hydroxy steroid
-
-
-
-
DELTA5-3beta-HSD
-
-
DELTA5-3beta-hydroxysteroid dehydrogenase
-
-
form 2 type 7 17beta-hydroxysteroid dehydrogenase
-
-
steroid 17beta-reductase
-
-
-
-
type 17beta-HSD
-
-
type 2 17beta-HSD
-
-
type 3 17beta-HSD
-
-
type 3 17beta-hydroxysteroid dehydrogenase
-
-
type 5 17-beta-hydroxysteroid dehydrogenase
-
additional information
-
the enzyme belongs to the short-chain alcohol dehydrogenase family
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
oxidation
reduction
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.
CAS REGISTRY NUMBER
COMMENTARY hide
9015-81-0
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
?
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
-
-
-
?
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
-
?
17-oxo steroids + NADPH
?
show the reaction diagram
-
maintenance of balance between oxidized and reduced steroids in blood
-
-
?
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
4-androstene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
5-androstenedione + NADPH
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
isozyme 17beta-HSD3
-
-
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
-
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
androstane-3,17-dione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstanedione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
androsterone + NADPH + H+
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
dehydroepiandrosterone + NAD(P)H + H+
androstendiol + NAD(P)+
show the reaction diagram
-
-
-
?
dehydroepiandrosterone + NAD+
4-androstene-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NAD+
androstene-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADPH + H+
5-androstene-3beta,17beta-diol + NADP+
show the reaction diagram
-
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
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 sulfate + NADP+
estrone sulfate + NADPH
show the reaction diagram
-
-
-
?
estrogenic estrone + NAD(P)H + H+
17beta-estradiol + NAD(P)+
show the reaction diagram
the product 17beta-estradiol plays a central role in the etiology of estrogen dependent diseases
-
-
?
estrone + NAD(P)H + H+
17beta-estradiol + NAD(P)+
show the reaction diagram
-
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
testosterone + NAD(P)+
androst-4-en-3,17-dione + NAD(P)H + H+
show the reaction diagram
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
show the reaction diagram
testosterone + NAD+
androst-4-en-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
-
r
testosterone + NADP+
androst-4-en-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
-
-
-
?
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
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
dihydrotestosterone + NADPH + H+
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
androsterone inactivation
-
-
?
estrogenic estrone + NAD(P)H + H+
17beta-estradiol + NAD(P)+
show the reaction diagram
the product 17beta-estradiol plays a central role in the etiology of estrogen dependent diseases
-
-
?
estrone + NADPH
estradiol + NADP+
show the reaction diagram
-
estrogen activation
-
-
?
testosterone + NAD(P)+
androstenedione + NAD(P)H + H+
show the reaction diagram
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
zymosterone + NADPH
zymosterol + NADP+
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
additional information
-
no activity with NADH in the forward reaction, poor activity with NAD+ in the reverse raection, overview
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,4-dihydroxyphenyl)-phenylmethanone
remaining 17beta HSD3 activity: 1.1%
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
12-acetyl-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
-
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
-
2,2',4,4'-tetrahydroxybenzophenone
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
-
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
-
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo(b,f)azocin-8-yl)-benzoic acid methyl ester
-
3-benzylidene camphor
remaining 17beta HSD3 activity: 56%
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
-
4-methylbenzylidene camphor
remaining 17beta HSD3 activity: 33%
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
-
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
-
androsterone
-
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
-
RM-532-105
-
(3a,5a)-3-[[(2R,5S)-4-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl]-2,5-dimethylpiperazin-1-yl]methyl]-17-methylideneandrostan-3-ol
-
-
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
-
i.e. RM-532-105
(4-(2,4-dichlorophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(2-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(2-methoxyphenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(3-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-bromophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chloro-2-(hydroxymethyl)phenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chloro-2-methylphenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chlorobenzoyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chlorobenzyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chlorophenyl)-1,4-diazepan-1-yl)(morpholino)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(1-oxido-4-thiomorpholino)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(3,4-dihydroisoquinolin-2(1H)-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(4-(2-hydroxyethyl)piperazin-1-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(4-methylpiperazin-1-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(cyclohexyl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(morpholino)methanethione
-
(4-(4-chlorophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(phenyl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(piperidin-1-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(pyridin-4-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(tetrahydro-2H-pyran-4-yl)methanone
-
(4-(4-chlorophenyl)piperazin-1-yl)(thiomorpholino)methanone
-
(4-(4-ethynylphenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-fluorophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-iodophenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(4-methoxyphenyl)piperazin-1-yl)(morpholino)methanone
-
(4-(6-bromopyridin-2-yl)piperazin-1-yl)(morpholino)methanone
-
(4-(6-chloropyridin-3-yl)piperazin-1-yl)(morpholino)methanone
-
(4-(biphenyl-4-yl)piperazin-1-yl)(morpholino)methanone
-
(5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)(morpholino)methanone
-
(S)-ibuprofen
-
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
-
IC50: 0.00297 mM
1-(4-(4-(4-chlorophenyl)piperazine-1-carbonyl)piperazin-1-yl)-2-hydroxyethanone
-
1-(4-(4-chlorophenyl)piperazine-1-carbonyl)piperidine-4-carboxylic acid
-
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
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-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
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
17beta-dihydroequilin
-
0.01 mM, 88% inhibition, reaction with 0.002 mM estradiol
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-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
-
IC50: 3 nM
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
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-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
3beta-phenylmethyl-androsterone
3beta-substituted androsterone derivatives
-
IC50: 57-147 nM
-
4-((4-(4-chlorophenyl)piperazin-1-yl)sulfonyl)morpholine
-
4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzoic acid
-
4-(4-chlorophenyl)-N-cyclohexylpiperazine-1-carboxamide
-
4-(4-chlorophenyl)-N-phenylpiperazine-1-carboxamide
-
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-[4-(4-chlorophenyl)piperazine-1-carbonyl]-thiomorpholine-1,1-dione
-
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
-
IC50: 0.00007 mM
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-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
albumin
-
-
-
beta-octylglucoside
-
strong
chloromercuribenzene-p-sulfonic acid
-
-
cyproterone acetate
-
-
danazol
-
inhibits oxidation of testosterone, 0.01 mM, 83% inhibition
dibenzothiazocine
-
IC50: 0.0004 mM
dodecyl-beta-D-maltoside
-
inhibition above 0.5%
EM-919
-
a 17beta-HSD type 2 inhibitor
epostane
-
-
estradiol
-
inhibits oxidation of testosterone
estrone
substrate inhibition
Flufenamic acid
-
flurbiprofen
-
gallic acid
-
0.001 mM, 50% inhibition, reduction of androst-4-en-3,17-dione
GTx-560
competitively and selectively inhibits AKR1C3-dependent androgen receptor transactivation. GTx-560 completely blocks the formation of testosterone from androstenedione, indicating the ability of AKR1C3 inhibitors, unlike 5alpha-reductase inhibitors, to reduce testosterone levels
indomethacin
-
Meclofenamic acid
-
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-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzoate
-
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 0.00014 mM
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
-
IC50: 2 nM
morpholino(4-(2-(trifluoromethyl)phenyl)piperazin-1-yl)methanone
-
morpholino(4-(4-nitrophenyl)piperazin-1-yl)methanone
-
morpholino(4-(naphthalen-2-yl)piperazin-1-yl)methanone
-
morpholino(4-(o-tolyl)piperazin-1-yl)methanone
-
morpholino(4-(p-tolyl)piperazin-1-yl)methanone
-
morpholino(4-(quinolin-3-yl)piperazin-1-yl)methanone
-
morpholino(4-phenylpiperazin-1-yl)methanone
-
-
morpholino-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)methanone
-
N,N-dimethyl-4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
N-(4-(4-(morpholine-4-carbonyl)piperazin-1-yl)phenyl)acetamide
-
N-(4-(4-(morpholine-4-carbonyl)piperazin-1-yl)phenyl)methanesulfonamide
-
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
-
IC50: 0.00016 mM
N-methyl-4-(4-(morpholine-4-carbonyl)piperazin-1-yl)benzamide
-
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
p-chloromercuribenzoate
-
-
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
-
testosterone
-
0.01 mM, 70% inhibition, reaction with 0.002 mM estradiol
tetrahydrodibenzazocine
-
IC50: 0.00009 mM
thiomorpholine
-
Triton X-100
-
significant
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
R1881
requires amino acids 1-282 of AKR1C3 to elicit its coactivation, inhibitor GTx-560 requires the full-length AKR1C3 to bind and inhibit R1881-induced activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00053
20alpha-dihydroprogesterone
-
pH 7.4, with NAD+ as cofactor
0.00001
dehydroepiandrosterone
-
37°C, 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
0.11 - 0.167
NAD+
0.0053 - 0.0056
NADH
9.6
NADP+
-
pH 7.4, reaction with estradiol
0.00061 - 0.24
testosterone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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 - 4.7
NAD+
0.27 - 0.33
NADH
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 hide
LITERATURE
IMAGE
0.0003
17alpha-ethynyl-estradiol
-
-
0.0006
danazol
-
-
0.0008
estradiol
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001
(2,4-dihydroxyphenyl)-phenylmethanone
Homo sapiens
pH 7.4, 37°C
0.00281
12-acetyl-11,12-dihydro-2-(trifluoromethyl)-6H-dibenzo(b,f)(1,4)thiazocine
Homo sapiens
pH and temperature not specified in the publication
0.0004
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
Homo sapiens
pH and temperature not specified in the publication
0.0181
2,2',4,4'-tetrahydroxybenzophenone
Homo sapiens
pH 7.4, 37°C
0.00915
2,5-dioxo-3-(2-propyn-1-yl)-3-pyrrolidinecarboxylic acid 2,3,3-triphenyl-2-propen-1-yl-ester
Homo sapiens
pH and temperature not specified in the publication
0.00006
2-((3-chloro-4-hydroxybenzoyl)amino)-N-(2-(2-methoxyphenyl)ethyl)-5-phenoxy-benzamide
Homo sapiens
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
Homo sapiens
pH and temperature not specified in the publication
0.033
3-benzylidene camphor
Homo sapiens
pH 7.4, 37°C
0.000116
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
Homo sapiens
pH and temperature not specified in the publication
0.0107
4-methylbenzylidene camphor
Homo sapiens
pH 7.4, 37°C
0.00024
5-acetyl-2-chloro-5,6-dihydro-dibenzo(b,f)azocine
Homo sapiens
pH and temperature not specified in the publication
0.00474
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
Homo sapiens
pH and temperature not specified in the publication
0.000182
androsterone
Homo sapiens
pH and temperature not specified in the publication
0.000035
N-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
Homo sapiens
pH and temperature not specified in the publication
0.000262
(3a,5a)-3-[[(2R,5S)-4-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl]-2,5-dimethylpiperazin-1-yl]methyl]-17-methylideneandrostan-3-ol
Homo sapiens
-
pH and temperature not specified in the publication
0.000085
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
Homo sapiens
-
pH and temperature not specified in the publication
0.00297
1-(11,12-dihydro-6H-dibenzo[b,f]oxocin-12-yl)ethanone
Homo sapiens
-
IC50: 0.00297 mM
0.00474
1-(5,6,11,12-tetrahydrodibenzo[b,f]azocin-12-yl)ethanone
Homo sapiens
-
IC50: 0.00474 mM
0.00000002
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]ethanone
Homo sapiens
-
IC50: 0.02 nM
0.00024 - 0.00029
1-[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanamine
0.0115
12-acetyl-1-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.0115 mM
0.0049
12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocin-3-ol
Homo sapiens
-
IC50: 0.0049 mM
0.00001
12-acetyl-2,3-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00001 mM
0.00281
12-acetyl-2-(trifluoromethyl)-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00281 mM
0.00003
12-acetyl-2-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00003 mM
0.00076
12-acetyl-3,4-dichloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00076 mM
0.00025
12-acetyl-3-bromo-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00025 mM
0.0001
12-acetyl-3-chloro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00010 mM
0.00009
12-acetyl-3-fluoro-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.00009 mM
0.0021
12-acetyl-3-methoxy-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.0021 mM
0.001
12-acetyl-3-methyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine
Homo sapiens
-
IC50: 0.001 mM
0.0009
17-hydroxy-7alpha-thioethyl-3-oxo-4-androstene-17alpha-propionic acid, gamma-lactone
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.0009 mM
0.000003
2-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 3 nM
0.000003
3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 3 nM
0.001
3-oxo-17alpha-pregna-4-ene-7alpha-(benzylthia)-21,17-carbolactone
Homo sapiens
-
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
Homo sapiens
-
IC50 for reduction of androst-4-en-3,17-dione: 0.001 mM
0.0011 - 0.0014
3-oxo-17alpha-pregna-4-ene-7alpha-(propylthia)-21,17-carbolactone
0.0007
3-oxo-17alpha-pregna-4-ene-7alpha-[4-[2-(1-piperidinyl)-ethoxy]benzylthia]-21,17-carbolactone
Homo sapiens
-
IC50 for oxidation of testosterone: 0.0007 mM, no inhibition of type 1, 3 and 5 17beta-HSD, nor against P450 aromatase
0.00007 - 0.00076
3alpha-ether-3beta-substituted androsterone derivatives
Homo sapiens
-
diverse derivatives, IC50: 70-760 nM, overview
-
0.000057 - 0.000147
3beta-alkylated androsterone derivatives
Homo sapiens
-
IC50: 57-147 nM
-
0.000073
3beta-phenylethyl-3alpha-methyl-O-androsterone
Homo sapiens
-
IC50: 73 nM
0.000099
3beta-phenylethyl-androsterone
Homo sapiens
-
IC50: 99 nM
0.000057
3beta-phenylmethyl-androsterone
Homo sapiens
-
IC50: 57 nM
0.000057 - 0.000147
3beta-substituted androsterone derivatives
Homo sapiens
-
IC50: 57-147 nM
-
0.000025
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)-N-methylbenzamide
Homo sapiens
-
IC50: 25 nM
0.000005
4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzonitrile
Homo sapiens
-
IC50: 5 nM
0.00000145
4-MA
Homo sapiens
-
37°C, pH not specified in the publication
0.00007
5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00007 mM
0.00024
5-acetyl-2-chloro-5,6-dihydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00024 mM
0.000003
5-acetyl-2-chloro-8-(2-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 3 nM
0.000008
5-acetyl-2-chloro-8-(3-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 8 nM
0.000002
5-acetyl-2-chloro-8-(4-methoxyphenyl)-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 2 nM
0.000004
5-acetyl-2-chloro-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 4 nM
0.00005
5-acetyl-3-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00005 mM
0.00049
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
Homo sapiens
-
IC50: 0.00049 mM
0.001
5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine-9-carboxamide
Homo sapiens
-
IC50: 0.001 mM
0.000009
5-acetyl-8-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 9 nM
0.00000002
5-acetyl-8-phenyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.02 nM
0.000007
5-acetyl-9-bromo-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 7 nM
0.000008
5-acetyl-N-cyclohexyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-amine
Homo sapiens
-
IC50: 8 nM
0.00028
9-bromo-11,12-dihydrodibenzo[b,f]azocine-5(6H)-carboxamide
Homo sapiens
-
IC50: 0.00028 mM
0.00032
9-bromo-5-butanoyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.00032 mM
0.001
9-bromo-5-ethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine
Homo sapiens
-
IC50: 0.001 mM
0.00015
cyproterone acetate
Homo sapiens
-
37°C, pH not specified in the publication
0.0004
dibenzothiazocine
Homo sapiens
-
IC50: 0.0004 mM
0.0000062
epostane
Homo sapiens
-
37°C, pH not specified in the publication
0.01
methyl 12-acetyl-11,12-dihydro-6H-dibenzo[b,f][1,4]thiazocine-3-sulfinate
Homo sapiens
-
IC50: 0.01 mM
0.00004
methyl 3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
Homo sapiens
-
IC50: 0.00004 mM
0.0000007 - 0.00004
methyl 4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)benzoate
0.00014
methyl [3-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
Homo sapiens
-
IC50: 0.00014 mM
0.000002
methyl [4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]amidosulfite
Homo sapiens
-
IC50: 2 nM
0.00016
N-(5-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocin-9-yl)benzamide
Homo sapiens
-
IC50: 0.00016 mM
0.00025
spiro-gamma-lactone-estradiol
Homo sapiens
-
inhibits the reduction of androst-4-en-3,17-dione, reversible, IC50: 0.00025 mM
0.0011
spironolactone
Homo sapiens
-
IC50 for oxidation of testosterone: 0.0011 mM
0.00009
tetrahydrodibenzazocine
Homo sapiens
-
IC50: 0.00009 mM
0.0000009
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
Homo sapiens
-
IC50: 0.9 nM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000000935
-
female abdominal skin, mean value, n=4, 37°C, pH not specified in the publication
0.0000000122
-
male inguinal skin, mean value, n=8, 37°C, pH not specified in the publication
0.0000000213
-
female perineal skin, mean value, n=4, 37°C, pH not specified in the publication
additional information
-
determination of serum and tumor tissue concentrations of steroids in prostate cancer patients, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
assay at
7.2
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
assay at
37
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
derived from an epidermoid carcinoma of the vulva
Manually annotated by BRENDA team
-
real-time RT-PCR expression 17beta-HSD type 2 analysis
Manually annotated by BRENDA team
-
male abdominal, 17beta-HSD type 2 is localized in the vasculature of the adipose compartment, real-time RT-PCR expression analysis
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
the enzyme is primarily expressed in the placenta and ovarian granulose cells
Manually annotated by BRENDA team
-
real-time RT-PCR expression 17beta-HSD type 2 analysis
Manually annotated by BRENDA team
-
isozyme 17beta-HSD5
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme catalyzes the last step in the biosynthesis of the potent androgen testosterone (T), by stereoselectively reducing the C17 ketone of 4-androstene-3,17-dione (4-dione), with NADPH as cofactor
drug target
the ratio of HSD17B1 to HSD17B2 is a good indicator of tamoxifen treatment benefit, as post-menopausal patients with tumors expressing a high HSD17B1/HSD17B2 protein ratio have less benefit from tamoxifen treatment
evolution
the enzyme belongs to the AKR1C family
malfunction
metabolism
physiological function
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
DHB3_HUMAN
310
3
34516
Swiss-Prot
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42300
-
2 * 42300, SDS-PAGE
64000
-
gel filtration
90400
-
glycerol gradient ultracentrifugation
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 42300, SDS-PAGE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme with inhibitor (4-(4-chlorophenyl)piperazin-1-yl)(morpholino)methanone bound in the actie site, X-ray diffraction structure determination and analysis, docking study and modelling
hanging-drop vapour diffusion method at 27°C, crystallization of the enzyme in complex with estrone and NADP+. His221 is the key residue responsible for the reorganization and stabilization of the reversely bound estrone, leading to the formation of a dead end complex, which exists widely in NADP(H)-preferred enzymes for the regulation of their enzymatic activity
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-15°C, a few percent loss of activity in several months
-
4°C, 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
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partial
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in HEK-293 cells by transient transfection
gene HSD17B3, recombinant expression in HEK-293 cells
AKR1C3, quantitative enzyme expression analysis by real-time PCR, recombinant expression in HEK-293 cells
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
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DNA and amino acid sequence determination and analysis, phylogenetic tree, transient expression in HEK-293 cells
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expression in Sf9 insect cells
gene HSD17B2, quantitative real-time RT-PCR enzyme expression analysis
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His6-tagged 17beta-HSD2 overexpressed in Sf9 cells
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overexpression in HEK-293 cells
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overexpression of type 3 17beta-HSD in HEK-293 cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
downregulation of CX3CL1, EPHB6, and TP63 increases HSD17B1 and HSD17B2 expression
estradiol negatively regulates HSD17B1 in breast cancer cell lines. Dihydrotestosterone has a primarily reductive impact on HSD17B1 expression
GREB1 downregulation suppresses HSD17B1
in non-small cell lung cancer (NSCLC) the expression of HSD17B1 is increased as compared with healthy tissue
miRNA-1304-3p reduces HSD17B1 expression
miRNA-17 upregulates HSD17B1
miRNA-210 and miRNA-7-5p have up- and down-regulatory effect
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
diagnostics
a high HSD17B1 to HSD17B2 ratio, as well as high HSD17B1 on its own is associated with worse prognosis and increased risk of recurrence in patients with ERalpha-positive tumors. An increased copy number of the HSD17B1 gene is correlated with decreased breast cancer survival
drug development
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the steroidogenic enzyme 17beta-hydroxysteroid dehydrogenase type 3 (17beta-HSD3) is a therapeutic target in the management of androgen-sensitive diseases such as prostate cancer and benign prostate hyperplasia
medicine
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inhibitor Strogen forte extract can be used for treatment of benign prostatic hyperplasia
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Mulder, E.; Lamers-Stahlhofen, G.J.M.; van der Molen, H.J.
Isolation and characterization of 17beta-hydroxy steroid dehydrogenase from human erythrocytes
Biochem. J.
127
649-659
1972
Homo sapiens
Manually annotated by BRENDA team
Khan, N.; Sharma, K.K.; Andersson, S.; Auchus, R.J.
Human 17beta-hydroxysteroid dehydrogenases types 1, 2, and 3 catalyze bi-directional equilibrium reactions, rather than unidirectional metabolism, in HEK-293 cells
Arch. Biochem. Biophys.
429
50-59
2004
Homo sapiens
Manually annotated by BRENDA team
Poirier, D.
Inhibitors of 17beta-hydroxysteroid dehydrogenases
Curr. Med. Chem.
10
453-477
2003
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Lu, M.L.; Huang, Y.W.; Lin, S.X.
Purification, reconstitution, and steady-state kinetics of the trans-membrane 17beta-hydroxysteroid dehydrogenase 2
J. Biol. Chem.
277
22123-22130
2002
Homo sapiens
Manually annotated by BRENDA team
Tchedam Ngatcha, B.; Luu-The, V.; Labrie, F.; Poirier, D.
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship
J. Med. Chem.
48
5257-5268
2005
Homo sapiens
Manually annotated by BRENDA team
Mindnich, R.; Haller, F.; Halbach, F.; Moeller, G.; Hrabe de Angelis, M.; Adamski, J.
Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme
J. Mol. Endocrinol.
35
305-316
2005
Homo sapiens, Danio rerio (Q6QA32), Danio rerio
Manually annotated by BRENDA team
Liu, H.; Robert, A.; Luu-The, V.
Cloning and characterization of human form 2 type 7 17beta-hydroxysteroid dehydrogenase, a primarily 3beta-keto reductase and estrogen activating and androgen inactivating enzyme
J. Steroid Biochem. Mol. Biol.
94
173-179
2005
Homo sapiens
Manually annotated by BRENDA team
Ngatcha, B.T.; Laplante, Y.; Labrie, F.; Luu-The, V.; Poirier, D.
3beta-Alkyl-androsterones as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: inhibitory potency in intact cells, selectivity towards isoforms 1, 2, 5 and 7, binding affinity for steroid receptors, and proliferative/antiproliferative activities on AR+ and ER+ cell lines
Mol. Cell. Endocrinol.
248
225-232
2006
Homo sapiens
Manually annotated by BRENDA team
Luu-The, V.; Tremblay, P.; Labrie, F.
Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women
Mol. Endocrinol.
20
437-443
2006
Homo sapiens
Manually annotated by BRENDA team
Fink, B.E.; Gavai, A.V.; Tokarski, J.S.; Goyal, B.; Misra, R.; Xiao, H.; Kimball, S.D.; Han, W.; Norris, D.; Spires, T.E.; You, D.; Gottardis, M.M.; Lorenzi, M.V.; Vite, G.D.
Identification of a novel series of tetrahydrodibenzazocines as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem. Lett.
16
1532-1536
2006
Homo sapiens
Manually annotated by BRENDA team
Degtyar, V.G.; Babkina, T.V.; Kazantseva, I.A.; Morozov, A.P.; Trapeznikova, M.F.; Kushlinskii, N.E.
Reductase activity of 17beta-hydroxysteroid oxidoreductase in prostatic tumors of different histological structure
Bull. Exp. Biol. Med.
139
715-717
2005
Homo sapiens
Manually annotated by BRENDA team
Lukacik, P.; Kavanagh, K.L.; Oppermann, U.
Structure and function of human 17beta-hydroxysteroid dehydrogenases
Mol. Cell. Endocrinol.
248
61-71
2006
Homo sapiens
Manually annotated by BRENDA team
Luu-The, V.; Ferraris, C.; Duche, D.; Belanger, P.; Leclaire, J.; Labrie, F.
Steroid metabolism and profile of steroidogenic gene expression in Episkin: high similarity with human epidermis
J. Steroid Biochem. Mol. Biol.
107
30-36
2007
Homo sapiens
Manually annotated by BRENDA team
Chura, J.C.; Ryu, H.S.; Simard, M.; Poirier, D.; Tremblay, Y.; Brooker, D.C.; Blomquist, C.H.; Argenta, P.A.
Steroid-converting enzymes in human ovarian carcinomas
Mol. Cell. Endocrinol.
301
51-58
2009
Homo sapiens
Manually annotated by BRENDA team
Nashev, L.G.; Schuster, D.; Laggner, C.; Sodha, S.; Langer, T.; Wolber, G.; Odermatt, A.
The UV-filter benzophenone-1 inhibits 17beta-hydroxysteroid dehydrogenase type 3: Virtual screening as a strategy to identify potential endocrine disrupting chemicals
Biochem. Pharmacol.
79
1189-1199
2010
Mus musculus, Rattus norvegicus, Homo sapiens (P37058), Homo sapiens
Manually annotated by BRENDA team
Tth, I.; Szcsi, M.; Julesz, J.; Faredin, I.; Behnke, B.
In vitro inhibition of testicular delta 5-3 beta-hydroxysteroid dehydrogenase and prostatic 5 alpha-reductase activities in rats and humans by strogen forte extract
Int. Urol. Nephrol.
28
337-348
1996
Homo sapiens, Rattus norvegicus, Rattus norvegicus Wistar
Manually annotated by BRENDA team
Tth, I.; Szcsi, M.; Julesz, J.; Faredin I.
Activity and inhibition of 3-beta-hydroxysteroid dehydrogenase/delta-5-4-isomerase in human skin
Skin Pharmacol. Physiol.
10
160-168
1997
Homo sapiens
Manually annotated by BRENDA team
Kenmogne, L.C.; Maltais, R.; Poirier, D.
Synthesis of a dansyl-labeled inhibitor of 17beta-hydroxysteroid dehydrogenase type 3 for optical imaging
Bioorg. Med. Chem. Lett.
26
2179-2183
2016
Homo sapiens
Manually annotated by BRENDA team
Flanagan, J.U.; Atwell, G.J.; Heinrich, D.M.; Brooke, D.G.; Silva, S.; Rigoreau, L.J.; Trivier, E.; Turnbull, A.P.; Raynham, T.; Jamieson, S.M.; Denny, W.A.
Morpholylureas are a new class of potent and selective inhibitors of the type 5 17-beta-hydroxysteroid dehydrogenase (AKR1C3)
Bioorg. Med. Chem.
22
967-977
2014
Homo sapiens (P42330)
Manually annotated by BRENDA team
Yepuru, M.; Wu, Z.; Kulkarni, A.; Yin, F.; Barrett, C.M.; Kim, J.; Steiner, M.S.; Miller, D.D.; Dalton, J.T.; Narayanan, R.
Steroidogenic enzyme AKR1C3 is a novel androgen receptor-selective coactivator that promotes prostate cancer growth
Clin. Cancer Res.
19
5613-5625
2013
Homo sapiens (P42330), Homo sapiens
Manually annotated by BRENDA team
Roy, J.; Fournier, M.A.; Maltais, R.; Kenmogne, L.C.; Poirier, D.
Reprint of in vitro and in vivo evaluation of a 3beta-androsterone derivative as inhibitor of 17beta-hydroxysteroid dehydrogenase type 3
J. Steroid Biochem. Mol. Biol.
153
170-178
2015
Rattus norvegicus (O54939), Homo sapiens (P37058), Rattus norvegicus Sprague-Dawley (O54939)
Manually annotated by BRENDA team
Mansour, M.F.; Pelletier, M.; Boulet, M.-M.; Mayrand, D.; Brochu, G.; Lebel, S.; Poirier, D.; Fradette, J.; Cianflone, K.; Luu-The, V.; Tchernof, A.
Oxidative activity of 17beta-hydroxysteroid dehydrogenase on testosterone in male abdominal adipose tissues and cellular localization of 17beta-HSD type 2
Mol. Cell. Endocrinol.
414
168-176
2015
Homo sapiens
Manually annotated by BRENDA team
Li, T.; Stephen, P.; Zhu, D.W.; Shi, R.; Lin, S.X.
Crystal structures of human 17beta-hydroxysteroid dehydrogenase type 1 complexed with estrone and NADP+ reveal the mechanism of substrate inhibition
FEBS J.
286
2155-2166
2019
Homo sapiens (P14061)
Manually annotated by BRENDA team
Aka, J.; Calvo, E.; Lin, S.
Estradiol-independent modulation of breast cancer transcript profile by 17beta-hydroxysteroid dehydrogenase type 1
Mol. Cell. Endocrinol.
439
175-186
2017
Homo sapiens (P14061)
Manually annotated by BRENDA team
Salah, M.; Abdelsamie, A.S.; Frotscher, M.
Inhibitors of 17?-hydroxysteroid dehydrogenase type 1, 2 and 14 Structures, biological activities and future challenges
Mol. Cell. Endocrinol.
489
66-81
2019
Homo sapiens (P14061)
Manually annotated by BRENDA team
Hilborn, E.; Stal, O.; Jansson, A.
Estrogen and androgen-converting enzymes 17beta-hydroxysteroid dehydrogenase and their involvement in cancer with a special focus on 17beta-hydroxysteroid dehydrogenase type 1, 2, and breast cancer
Oncotarget
8
30552-30562
2017
Homo sapiens (P14061)
Manually annotated by BRENDA team
Hilborn, E.; Stal, O.; Alexeyenko, A.; Jansson, A.
The regulation of hydroxysteroid 17beta-dehydrogenase type 1 and 2 gene expression in breast cancer cell lines by estradiol, dihydrotestosterone, microRNAs, and genes related to breast cancer
Oncotarget
8
62183-62194
2017
Homo sapiens (P14061)
Manually annotated by BRENDA team