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(12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
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(1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
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(1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
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(1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
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(1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
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(1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
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(1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
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(4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
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(4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
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+/-gossypol
potent, competitive
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16-cyano-17-keto-trilostane
i.e 2,16-dicyano-4,5-epoxy-androstane-3,17-dione. Competitive, selective inhibitor of wild-type enzyme and chimeric S194G-1 mutant of the enzyme (3beta-HSD1). Noncompetitive inhibitor of chimeric R195P-1 mutant of the enzyme. Selective inhibition of 3beta-HSD1 may prevent spontaneous premature birth; i.e 2,16-dicyano-4,5-epoxy-androstane-3,17-dione. noncompetitive inhibitor; selective inhibitor
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17alpha-hydroxypregnenolone
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competitive inhibition
17beta-acetoxy-trilostane
-
-
2,16-dicyano-4,5-epoxy-androstane-3,17-dione
competitively inhibits 3beta-HSD1
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20alpha-hydroxy-4-pregnen-3-one
-
-
20beta-hydroxy-4-pregnen-3-one
-
-
3-Chloroacetylpyridine adenine dinucleotide
-
-
4-nonylphenol
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downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
4alpha,5alpha-epoxy-testosterone
-
-
5'-fluorosulfonylbenzoyl adenosine
-
-
5,10-Secoestr-4-yne-3,10,17-trione
-
irreversible
bis (2-butoxyethyl) phthalate
moderate inhibitor, competitive
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bisphenol A
potent, competitive
Cetylpyridinium chloride
-
-
corticosterone
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0.08 mM, 50% inhibition
cyanoketone
-
0.0000076 mM, 50% inhibition; competitive
dehydroepiandrosterone
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0.01 mM reduced conversion of pregnenolone to 50%
di-heptyl phthalate
potent inhibitor, competitive
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di-n-butyl phthalate
potent inhibitor, competitive
di-n-octyl phthalate
weak inhibitor
dicyclohexyl phthalate
moderate inhibitor, competitive
diethylhexyl phthalate
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downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
diethylstilbestrol
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downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
estradiol
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0.0005 mM, 40% inhibition, 0.001 mM, 62% inhibition
etomidate
very potent, competitive
Fe2+
-
1 mM: weak, 100 mM: strong
flavanones
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diverse derivatives, inhibitory potential determination, overview
flavones
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diverse derivatives, inhibitory potential determination, overview
HPTE
potent inhibitor, competitive
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isoflavones
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diverse derivatives, inhibitory potential determination, overview
lauric acid
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0.05 mM, less than 10% inhibition
medroxyprogesterone
potent
monooctyltin
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0.081 mM, 50% inhibition; inhibition mechanism, overview
myristic acid
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0.05 mM, less than 10% inhibition
N-(Anilino-naphthyl-4)-maleimide
-
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N-Iodoacetyl-N'-(5-sulfo-1-naphthyl)ethylene diamine
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-
NADH
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mixed type inhibition
octylphenol
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downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
oestradiol
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0.00024 mM, 50% inhibition
organotin
can inhibit placental HSD3B1 activity, thus blocking the formation of progesterone and disrupting pregnancy
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pregnenolone
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competitive inhibition
resveratrol
potent, competitive
Triphenyltin
potent, competitive
(+)-gossypol
-
potent inhibitor
(+)-gossypol
potent inhibitor, competitive
(+)-gossypol
-
potent inhibitor
(-)-gossypol
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potent inhibitor
(-)-gossypol
weak inhibitor, competitive
(-)-gossypol
-
potent inhibitor
6-hydroxyflavone
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0.00056 mM, 50% inhibition; competitive
6-hydroxyflavone
very potent, competitive
apigenin
-
-
apigenin
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0.13 mM, 50% inhibition
Biochanin A
-
-
Biochanin A
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0.00094 mM, 50% inhibition
Cd2+
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1 mM: strong
Co2+
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1 mM: weak, 100 mM: strong
Cu2+
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1 mM: strong
daidzein
-
-
daidzein
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0.0033 mM, 50% inhibition
epostane
-
-
epostane
inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 1417fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y; inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 1417fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y
epostane
-
competitive inhibition
epostane
inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2
ethynylestradiol
-
-
formononetin
-
-
formononetin
-
0.0032 mM, 50% inhibition
genistein
-
-
genistein
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0.00026 mM, 50% inhibition; competitive
genistein
very potent, competitive
ketoconazole
very potent
ketoconazole
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downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
methoxychlor
moderate, noncompetitive
methoxychlor
insecticide, potent inhibitor, competitive
myricetin
-
0.011 mM, 50% inhibition
Ni2+
-
1 mM: weak, 100 mM: strong
Norethisterone
-
-
Norethisterone acetate
-
-
Norethisterone acetate
-
-
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
-
progesterone
-
-
progesterone
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0.026 mM, 50% inhibition
progesterone
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0.025 mM, 44% inhibition, 0.05 mM, 67% inhibition
quercetin
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0.084 mM, 50% inhibition
testosterone
-
0.0086 mM, 50% inhibition
tributyltin
potent, competitive
tributyltin
moderate inhibitor, competitive
tributyltin
-
0.012 mM, almost complete loss of activity; complete inhibition at 0.012 mM, the inhibition mechanism is not entirely competitive, overview
trilostane
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i.e. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-en-2-carbonitrile
trilostane
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i.e. 2alpha-cyano-4alpha,5alpha-epoxy-17beta-ol-androstane-3-one
trilostane
-
i.e. 2alpha-cyano-4alpha,5alpha-epoxy-17beta-ol-androstane-3-one, competitive inhibition
trilostane
-
human adrenal H295R cells treated with the HSD3B2 inhibitor, trilostane, demonstrate a markedly decreased androstenedione production
trilostane
inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2. Trilostane is docked in the active site of isoform 3beta-HSD1, and residue Arg195 in 3beta-HSD1 is a potentially critical residue
trilostane
noncompetitive inhibitor; noncompetitive inhibitor of chimeric S194G-1 mutant and chimeric R195P-1 mutant of the enzyme (3beta-HSD1). Competitive inhibition of wild-type enzyme
trilostane
-
0.004 mM, 50% inhibition
trilostane
-
0.005 mM, 56% inhibition, 0.025 mM, 90% inhibition; potent inhibition
trilostane
-
treatment does not affect transcription or translation in liver or adrenal
trilostane
specific enzyme inhibitor
trilostane
-
specific inhibitor
additional information
-
structure-inhibition relationship
-
additional information
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no inhibition by quercetin, apigenin, genistein, daidzein, enterodiol, and enterolactone
-
1.1.1.145 3beta-hydroxy-DELTA5-steroid dehydrogenase
results (
results (
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