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

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Homo sapiens


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


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
1.1.1.51
-
RECOMMENDED NAME
GeneOntology No.
3(or 17)beta-hydroxysteroid dehydrogenase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
testosterone and androsterone degradation to androstendione
-
-
androgen and estrogen metabolism
-
-
Steroid hormone biosynthesis
-
-
Steroid degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
the enzyme belongs to the AKR1C family
malfunction
-
AKR1C3 siRNA reduces androgen receptor signaling in VCaP cells. Small-molecule inhibitors inhibit both the enzymatic and coactivator functions of AKR1C3 resulting in androgen-dependent prostate cancer and CRPC regression
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
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
-
?
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
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
reduction at C17
-
-
?
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
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
-
-
-
?
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
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 SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
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
-
-
?
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
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,4-dihydroxyphenyl)-phenylmethanone
-
remaining 17beta HSD3 activity: 1.1%
(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-[(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
-
-
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
-
-
12-acetyl-11,12-dihydro-6H-dibenzo(b,f)(1,4)thiazocine
-
-
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
-
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
-
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
-
-
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-benzylidene camphor
-
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
-
-
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-chlorophenyl)-4-piperazinylcarbonyl)-1,1-dioxide
-
-
-
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-methylbenzylidene camphor
-
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
-
-
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
-
-
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
-
-
-
androsterone
-
-
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
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
-
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
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-(((3,5)-3-hydroxy-17-oxoandrostan-3-yl)methyl)-N-(tricyclo(3.3.1.13.7)dec-2-ylmethyl)butanamide
-
-
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
-
-
naproxen
-
-
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
p-chloromercuribenzoate
-
-
RM-532-105
-
-
-
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
0.000262
(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
0.00281
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
0.0049
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
0.0181
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
0.000003
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
0.033
3-benzylidene camphor
Homo sapiens
-
pH 7.4, 37°C
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
0.000116
3alpha-butyl-3-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
pH and temperature not specified in the publication
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
0.0107
4-methylbenzylidene camphor
Homo sapiens
-
pH 7.4, 37°C
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-dihydro-dibenzo(b,f)azocine
Homo sapiens
-
pH and temperature not specified in the publication
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
0.00474
5-acetyl-5,6,11,12-tetrahydro-dibenzo(b,f)(1,4)diazocine
Homo sapiens
-
pH and temperature not specified in the publication
0.00049
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
0.000182
androsterone
Homo sapiens
-
pH and temperature not specified in the publication
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
0.000035
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
0.00016
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
7.2
-
assay at
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
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
-
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
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42300
-
2 * 42300, SDS-PAGE
64000
-
gel filtration
90400
-
glycerol gradient ultracentrifugation
SUBUNITS
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
-
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
-
partial
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
-
DNA and amino acid sequence determination and analysis, phylogenetic tree, transient expression in HEK-293 cells
-
expressed in HEK-293 cells by transient transfection
-
gene HSD17B2, quantitative real-time RT-PCR enzyme expression analysis
-
gene HSD17B3, recombinant expression in HEK-293 cells
-
His6-tagged 17beta-HSD2 overexpressed in Sf9 cells
-
overexpression in HEK-293 cells
-
overexpression of type 3 17beta-HSD in HEK-293 cells
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
AKR1C3 siRNA reduces androgen receptor signaling in VCaP cells
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
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
-
inhibitor Strogen forte extract can be used for treatment of benign prostatic hyperplasia