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1.1.1.51: 3(or 17)beta-hydroxysteroid dehydrogenase

This is an abbreviated version!
For detailed information about 3(or 17)beta-hydroxysteroid dehydrogenase, go to the full flat file.

Word Map on EC 1.1.1.51

Reaction

testosterone
+
NAD(P)+
=
androstenedione
 +
NAD(P)H
 +
H+

Synonyms

17 beta-HSD3, 17 beta-hydroxysteroid dehydrogenase, 17-beta-HSD, 17-ketoreductase, 17beta-HSD, 17beta-HSD (type 1), 17beta-HSD (type 3), 17beta-HSD type 2, 17beta-HSD type 3, 17beta-HSD type II, 17beta-HSD-3, 17beta-HSD1, 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, 17beta-hydroxysteroid dehydrogenases type 2, 17beta-hydroxysteroid oxidoreductase, 17beta-hydroxysteroid: NADP 17-oxidoreductase, 17betaHSD2, 3 beta-hydroxysteroid dehydrogenase, 3,17beta-HSD, 3,17beta-hydroxysteroid dehydrogenase, 3-beta HSD, 3beta,17beta-hydroxysteroid dehydrogenase, 3beta-HSD, 3beta-HSD (type 1), 3beta-HSD type-I, 3beta-HSD type-II, 3beta-HSD/isomerase, 3beta-hydroxy steroid dehydrogenase, 3beta-hydroxy-steroid dehydrogenase/DELTA5-DELTA4 isomerase, 3beta-hydroxysteroid dehydrogenase, 3beta-hydroxysteroid dehydrogenase/DELTA5-4-isomerase, 3beta-hydroxysteroid dehydrogenase/DELTA5-DELTA4-isomerase, 3beta-hydroxysteroid dehydrogenase/isomerase, 3beta-hydroxystroid oxidoreductase, 3beta/17beta-HSD, 3beta/17beta-hydroxysteroid dehydrogenase, 3beta17betaHSDH, 3betaHSD, AKR1C3, AKR1C35, aldo keto reductase 1C3, beta-hydroxy steroid dehydrogenase, betahsd, 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, HSD, HSD17B1, HSD17B3, LOC101842245, More, pQ3 beta HSD, RDH11, Rdh11/12-like 1, Rdh11/12-like 2, Rdh11/12-like 3, retinol dehydrogenases 11-like, 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

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.51 3(or 17)beta-hydroxysteroid dehydrogenase

Inhibitors

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

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,4-dihydroxyphenyl)-phenylmethanone
(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
(3alpha,5alpha)-3-[(2,5-dimethyl-4-{[2-(trifluoromethyl)phenyl]sulfonyl}piperazin-1-yl)methyl]-3-hydroxyandrostan-17-one
the inhibitor RM-532-105 seems to have difficulties in penetrating inside the testis and is concentrated in the testicular capsule. Therefore it is unable to inhibit the 17bets-HSD3 located inside the testis. At a higher concentration, RM-532-105 significantly decreases the level of testosterone and dihydrotestosterone in rat plasma, in vivo effects of the inhibitor in testis and plasma, detailed overview
(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
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
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-(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%
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-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
albumin
-
-
-
androstenedione
-
-
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
Dimethylsulfoxide
-
-
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
glycerol
-
-
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
-
Iodosobenzoate
-
-
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
-
oleuropein glycoside
-
0.001 mM, 40% inhibition, reduction of androst-4-en-3,17-dione
p-chloromercuribenzoate
Perfluorooctanoic acid
-
-
Propyleneglycol
-
-
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
-
testosterone
-
0.01 mM, 70% inhibition, reaction with 0.002 mM estradiol
tetrahydrodibenzazocine
-
IC50: 0.00009 mM
thiomorpholine
-
Triton X-100
Tween-80
-
-
[4-(5-acetyl-2-chloro-5,6,11,12-tetrahydrodibenzo[b,f]azocin-8-yl)phenyl]methanol
-
IC50: 0.9 nM
additional information
-