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(2,4-dihydroxyphenyl)-phenylmethanone
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(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
93.3% inhibition at 0.1 mM
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
89.1% inhibition at 0.1 mM
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
92.7% inhibition at 0.1 mM
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
93.5% inhibition at 0.1 mM
(3,6-dihydropyridin-1(2H)-yl)(1H-indol-2-yl)methanone
crystal structure analysis of enzyme-inhibitor complex
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
(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
(3alpha,5alpha)-3-[[trans-2,5-dimethyl-4-[[2-(trifluoromethyl)-phenyl]sulfonyl]piperazin-1-yl]methyl]-3-hydroxyandrostan-17-one
strong inhibition of isoform 17beta-HSD3 overexpressed in HEK-293 cells
(3R,10S,13S)-3-(Adamantan-1-ylmethyl-butyl-amino)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
IC50: 80 nM
(3R,10S,13S)-3-[(2-Cyclopentyl-ethyl)-morpholin-4-yl-amino]-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
IC50: 74 nM
(3R,5'R,10S,13S)-4',5'-dibenzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
6.2-19.5% inhibition at 0.0001-0.001 mM
(3R,5'R,10S,13S)-5'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
58.2-90.4% inhibition at 0.0001-0.001 mM
(3R,5'S,10S,13S)-4',5'-dibenzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
25.6-87.3% inhibition at 0.0001-0.001 mM
(3R,5'S,10S,13S)-5'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
18.5-63.2% inhibition at 0.0001-0.001 mM
(3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-(2-methylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(2-phenylethyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(3-phenylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(4-phenylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-en-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-yn-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(4-phenoxyphenyl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(5-phenoxy-1H-1,2,3-triazol-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-2-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[2-[4-(trifluoromethyl)phenyl]ethyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzene-1-sulfonyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzoyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[2-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethoxy)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-3'-benzyl-10,13-dimethyltetradecahydro-2'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidine]-2',17(2H)-dione
strong inhibition of isoform 17beta-HSD3 overexpressed in HEK-293 cells. 44% inhibition at 0.1 microM in homogenized cells
(3R,5S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[(4-bromophenyl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[([1,1'-biphenyl]-4-yl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[[2,4-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[[3,5-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3S)-3,4-dibenzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
(3S)-3-benzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
(3S)-3-benzyl-4-(prop-2-yn-1-yl)-1-oxa-4-azaspiro[5.5]undecan-2-one
-
-
(3S)-3-benzyl-4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-1-oxa-4-azaspiro[5.5]undecan-2-one
-
-
(5-methyl-1H-indol-2-yl)(4-propylpiperidin-1-yl)methanone
crystal structure analysis of enzyme-inhibitor complex
(5alpha)-3-hydroxyandrostan-17-one
-
-
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
(RS)-3(3'-phenylpropoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
-
IC50: 0.0421 mM
1-(4-hydroxyphenyl)-butan-1-one
-
IC50: 0.08951 mM
1-(4-hydroxyphenyl)-ethanone
-
IC50: 1.70892 mM
1-(4-hydroxyphenyl)-heptan-1-one
-
IC50: 0.0784 mM
1-(4-hydroxyphenyl)-hexan-1-one
-
IC50: 0.01802 mM
1-(4-hydroxyphenyl)-nonan-1-one
-
IC50: 0.00286 mM
1-(4-hydroxyphenyl)-octan-1-one
-
IC50: 0.00652 mM
1-(4-hydroxyphenyl)-pentan-1-one
-
IC50: 0.00497 mM; IC50: 0.06052 mM
1-(4-hydroxyphenyl)-propan-1-one
-
IC50: 0.15056 mM
1-(4-hydroxyphenyl)-undeca-1-one
-
IC50: 0.00755 mM
1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM
1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM
1-methyl-3,17-dione-androsta-1,4-diene
-
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-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM
2,5-diphenyl-p-benzoquinone
-
IC50: 0.0027 mM, reduction of androstenedione
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4
2-methylcinnamic acid
-
IC50: 0.0064 mM
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
-
3,4,5-trimethoxycinnamic acid
-
IC50: 0.049 mM
3-((4-nitronaphthalen-1-yl)amino)benzoic acid
inhibitor nanomolar potency and selective inhibition of isoform AKR1C3 but also acts as an androgen receptor antagonist. It inhibits 5alpha-dihydrotestosterone stimulated androgen receptor reporter gene activity with an IC50 value of 4.7 microM and produces a concentration dependent reduction in androgen receptor levels in prostate cancer cells
3-(17'-oxo-5'alpha-androstan-3'alpha-oxy)propanoic acid
-
0.003 mM, 48% inhibition
3-(4-Bromo-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.0083 mM, reduction of androstenedione
3-(4-Chloro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.0018 mM, reduction of androstenedione
3-(4-Fluoro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.007 mM, reduction of androstenedione
3-coumaric acid
-
34% inhibition at 0.05 mM
3-cyclohexyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-cyclohexylmethyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-cyclohexylpropanoic acid
-
weak inhibition, IC50: 0.1 mM, above
3-hexyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-octyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-phenethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-phenyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-pentyl-2-[[(pyridin-2-yl)methyl]sulfanyl]-7-(pyrrolidine-1-carbonyl)quinazolin-4(3H)-one
crystal structure analysis of enzyme-inhibitor complex
3-phenoxybenzoic acid
inhibitor carboxylic acid binds to the oxyanion site, in which the carboxylate group very closely overlays the acetate molecule found in other AKR1C3 structures and forms hydrogen bonds to the enzyme catalytic residues His117 and Tyr55, as well as to a conserved water network located in and near the SP3 subpocket. The 3-phenoxy ring extends into the SP1 subpocket and makes van der Waals contacts with the aromatic residues Phe306, Phe311 and Tyr319 that line the pocket
3-trifluoromethylcinnamic acid
-
IC50: 0.043 mM
3-[(4-nitrophenyl)amino]benzoic acid
94fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
360fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
inhibitor shows 17fold and 30fold selectivity against isoforms AKR1C2 and AKR1C1, respectively, and much higher selectivity against AKR1C4
3alpha,3beta-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one
-
0.003 mM, 53% inhibition
3alpha-(2'-hydroxypropanoxy)-5alpha-androstan-17-one
-
0.003 mM, 89% inhibition
3alpha-(3'-bromopropanoxy)-5alpha-androstan-17-one
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0.003 mM, 93% inhibition
3alpha-(3'-hydroxypropanoxy)-5alpha-androstan-17-one
-
0.003 mM, 86% inhibition
3alpha-(prop-2'-enoxy)-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition
3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 352 nM
3alpha-ethoxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition
3alpha-hexanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 28% inhibition
3alpha-hexanoxy-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition
3alpha-hydroxy-3'-phenyl-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 81 nM
3alpha-hydroxy-3beta-(3'-hydroxypropyl)-5alpha-androstan-17-one
-
0.003 mM, 74% inhibition
3alpha-hydroxy-3beta-(prop-2'-enyl)-5alpha-androstan-17-one
-
0.003 mM, 76% inhibition
3alpha-hydroxy-3beta-methyl-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3alpha-hydroxy-3beta-octyl-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 147 nM
3alpha-hydroxy-3beta-phenylethyl-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 99 nM
3alpha-hydroxy-3beta-phenylmethyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition, IC50: 57 nM
3alpha-hydroxy-3beta-phenylpropyl-5alpha-androstan-17-one
-
0.003 mM, 97% inhibition
3alpha-hydroxy-3beta-propyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition, IC50: 67 nM
3alpha-hydroxy-3beta-vinyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
3alpha-methoxy-3beta-(2'-phenylethyl)-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 73 nM
3alpha-methoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 154 nM
3alpha-methoxy-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
3alpha-O-(spirotetrahydrofuran-2-yl)-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
3alpha-propanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 87% inhibition
3alpha-propanoxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3b-Methyl-5a-androstan-3a-ol-17-on
-
-
3beta,3alpha-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3beta-(2'-cyclohexylethyl)-3alpha-methoxy-5alpha-androstan-17-one
-
0.003 mM, 88% inhibition, IC50: 354 nM
3beta-cyclohexyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 97 nM
3beta-cyclohexylethyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 60 nM
3beta-cyclohexylethyl-androsterone
-
IC50: 60 nM
3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 87 nM
3beta-dodecyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 77% inhibition
3beta-hydroxy-3alpha-(3'-hydroxypropyl)-5alpha-androstan-17-one
-
0.003 mM, 17% inhibition
3beta-hydroxy-3alpha-(prop-2'-enyl)-5alpha-androstan-17-one
-
0.003 mM, 36% inhibition
3beta-hydroxy-3alpha-methyl-5alpha-androstan-17-one
-
0.003 mM, 16% inhibition
3beta-hydroxy-3alpha-phenyl-5alpha-androstan-17-one
-
0.003 mM, 39% inhibition
3beta-hydroxy-3alpha-phenylmethyl-5alpha-androstan-17-one
-
0.003 mM, 39% inhibition
3beta-hydroxy-3alpha-propyl-5alpha-androstan-17-one
-
0.003 mM, 33% inhibition
3beta-n-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 116 nM
3beta-n-hexyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 100 nM
3beta-phenylmethyl-androsterone
-
IC50: 57 nM
3beta-propyl-androsterone
-
IC50: 67 nM
3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 90% inhibition, IC50: 73 nM
3beta-sec-butyl-androsterone
-
IC50: 73 nM
3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 142 nM
4-chloro-N-[(4-chlorophenyl)methyl]-5-nitro-1H-pyrazole-3-carboxamide
crystal structure analysis of enzyme-inhibitor complex
4-nitro-2-([4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl)phenol
crystal structure analysis of enzyme-inhibitor complex
5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1,3-thiazol-2-one
5-(3-bromo-4-hydroxybenzylidene)-3-(4-fluorophenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-bromo-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one
compound demonstrates significant selectivity for isoform 17beta-hydroxysteroid dehydrogenase type 3 over the related isoenzymes and nuclear receptors. IC50 value 14 nM in cell-based assay
5-(3-bromo-4-hydroxybenzylidene)-3-(4-methylphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-tioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(benzenesulfonyl)-2-nitrophenol
crystal structure analysis of enzyme-inhibitor complex
5-androstene-3,17-dione
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5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
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5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
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5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
Biochanin A
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IC50: 0.0108 mM, reduction of androstenedione
bis(2-butoxyethyl) phthalate
caffeic acid
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18% inhibition at 0.05 mM
Cinnamic acid
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IC50: 0.050 mM
clomiphene
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IC50: 0.0762 mM
coumarin-3-carboxylic acid
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30% inhibition at 0.05 mM
CuCl2
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10 mM, 40% inhibition
Cyclopropanecarboxylic acid ((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-octyl-amide
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IC50: 57 nM
Cyclopropanecarboxylic acid cyclohexylmethyl-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-amide
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IC50: 85 nM
FeCl3
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10 mM, 54% inhibition
heptanoic acid (1-{1-[(3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-ylmethyl)-carbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-amide
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IC50: 227 nM
methyl (2R)-2-[(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]-4-methylpentanoate
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methyl (2R)-[(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](phenoxy)acetate
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methyl (2S)-2-[(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]-4-methylpentanoate
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methyl (2S)-[(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](phenoxy)acetate
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methyl [(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]acetate
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N-Adamantan-1-ylmethyl-N-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-butyramide
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IC50: 35-57 nM
p-chloromercuribenzoate
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10 mM, strong inhibition, 5% residual activity is reversed to 65% activity by either 1 mM glutathione or cysteine
Pb(NO3)2
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10 mM, 30% inhibition
phenyl-p-benzoquinone
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IC50: 0.0057 mM, reduction of androstenedione
Sodium amytal
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10 mM, 25% inhibition
Sodium cyanide
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10 mM, progressive and marked inhibition
STX2171
ability to penetrate the cell. Lack of inhibition of 17beta-HSD2 (the enzyme that catalyzes the opposite reaction to that of 17beta-HSD3, which is the oxidation of active testosterone to inactive androstenedione)
tamoxifen
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IC50: 0.098 mM, time-dependent and irreversible
testosterone
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1 mM, 62.8% inhibition of androstendione reduction
ZnCl2
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10 mM, 90% inhibition
(+)-gossypol
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(-)-gossypol
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(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
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(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
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48.8-92.0% inhibition at 0.0001-0.001 mM
(3S)-3,4-dibenzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
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(3S)-3,4-dibenzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
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47.3-92.1% inhibition at 0.0001-0.001 mM
(3S)-3-benzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
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(3S)-3-benzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
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24.2-24.3% inhibition at 0.0001-0.001 mM
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
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IC50: 0.0091 mM, reduction of androstenedione
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
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IC50: 0.00915 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
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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
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3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
250fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
in complex with AKR1C3. Compound adopts a similar binding orientation as flufenamic acid, however, its phenylamino ring projects deeper into a subpocket and confers selectivity over the other AKR1C isoforms
4-Methylumbelliferone
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IC50: 0.0009 mM, reduction of androstenedione
4-Methylumbelliferone
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IC50: 0.0019 mM
5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1,3-thiazol-2-one
starting compound for high-throughput screening. IC50 value 570 nM in cell-based assay
5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1,3-thiazol-2-one
selective non-steroidal 17beta-HSD3 inhibitor that does not show any undesired inhibition of estrogen biosynthesis and does not possess the transcriptional activity against any of these nuclear receptors
5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
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strong inhibitory activity on isoform 3beta-HSD3. When administered orally at a high dose of 100 mg/kg, compound shows approximately two times more potent testosterone-lowering effect against a positive control in the luteinizing hormone-releasing hormone-induced T production assay. The T-lowering effect continues at ca 10% level of control over 4 h after administration
7-hydroxyflavone
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IC50: 0.009 mM, reduction of androstenedione
7-hydroxyflavone
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IC50: 0.06698 mM
baicalein
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IC50: 0.0093 mM, reduction of androstenedione
baicalein
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IC50: 0.18592 mM
bis(2-butoxyethyl) phthalate
potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
bis(2-butoxyethyl) phthalate
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potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
canadine
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corydaline
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corypalmine
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dicyclohexyl phthalate
potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
dicyclohexyl phthalate
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potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
RM-532-105
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RM-532-105
the inhibitor RM-532-105 seems to have difficulty penetrating the testis and was found to be concentrated in the testicular capsule, therefore unable to inhibit the 17beta-HSD3 located inside the testis
scoulerine
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Stylopine
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Stylopine
the most potent inhibitor among the tested compounds that exhibited moderate selectivity towards AKR1C3 versus AKR1C1, EC 1.1.1.62. Stylopine significantly inhibits the AKR1C3-mediated reduction of daunorubicin in intact cells without considerable cytotoxic effects
tetrahydrocolumbamine
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tetrahydroplamatine
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umbelliferone
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IC50: 0.0014 mM, reduction of androstenedione
umbelliferone
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IC50: 0.0014 mM
additional information
crystal structures of complexes of 17beta-HSD5 with structurally diverse inhibitors derived from high-throughput inhibitor screening, overview. Analysis of interactions between 17beta-HSD5 and inhibitors at the atomic level which enable structure-based drug design for anti-CRPC therapy
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additional information
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design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3, structure-activity relationship study, overview
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additional information
nineteen isoquinoline alkaloids were examined for their ability to inhibit a recombinant AKR1C3 enzyme
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additional information
activity of 17beta-HSD is significantly decreased in metyrapone-induced corticosterone-deficient rat Leydig cells compared to control, whereas simultaneous administration of corticosterone partially prevented this and maintained the activity at near normal levels
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additional information
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synthesis of 3-spiromorpholinone androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3, overview
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