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Information on EC 1.3.99.5 - 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor) and Organism(s) Homo sapiens and UniProt Accession P31213

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EC Tree
IUBMB Comments
A flavoprotein. This bacterial enzyme, characterized from Comamonas testosteroni, is involved in androsterone degradation. cf. EC 1.3.1.22, 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+).
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This record set is specific for:
Homo sapiens
UNIPROT: P31213
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The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
5alpha-reductase, srd5a2, srd5a1, 5alpha-r, steroid 5alpha-reductase, 5alpha-reductase type 2, 5alpha-reductase type 1, 5alphar1, 5alpha reductase, 5alphar2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3-oxo-steroid-4-ene dehydrogenase
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5alpha-reductase
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5alpha-reductase type 2
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5alpha-reductase type II
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5alpha-reductase type2
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SRD5alpha
SRD5alpha enzymes form the oxidoreductase superfamily
steroid-5alpha-reductase
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type II 5alpha-reductase
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3-keto-DELTA4-steroid-5 alpha-reductase
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3-ketosteroid-DELTA4(5alpha)-dehydrogenase
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3-oxo-5alpha-steroid DELTA4-dehydrogenase
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3-oxo-steroid-4-ene dehydrogenase
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3-oxosteroid DELTA4-dehydrogenase
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4-ene-3-ketosteroid-5alpha-oxidoreductase
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5 alpha-SR2
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-
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5-alpha reductase II
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5alpha reductase
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5alpha-R
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5alpha-reductase
5alpha-reductase II
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5alpha-reductase type1
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5alphaR1
5alphaR2
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5AR2
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dehydrogenase, 3-oxo-5alphasteroid DELTA4-
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DELTA4(5alpha)DH
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DELTA4-3-keto steroid 5alpha-reductase
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DELTA4-3-ketosteroid 5alpha-oxidoreductase
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DELTA4-3-oxo steroid reductase
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DELTA4-3-oxosteroid-5alpha-reductase
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DELTA4-5alpha-dehydrogenase
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NADPH-dependent 5alpha-reductase enzyme
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S5alphaRI
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S5alphaRII
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S5AR
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SRD5A2
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steroid 5-alpha-reductase type 2
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steroid 5alpha-reductase
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steroid 5alpha-reductase type 2
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steroid DELTA4-5alpha-reductase
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testosterone 5alpha-reductase
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type 1 5alpha-reductase
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type 2 5alpha-reductase
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type I 5alpha-reductase
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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oxidation
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3-oxo-5alpha-steroid:acceptor DELTA4-oxidoreductase
A flavoprotein. This bacterial enzyme, characterized from Comamonas testosteroni, is involved in androsterone degradation. cf. EC 1.3.1.22, 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+).
CAS REGISTRY NUMBER
COMMENTARY hide
9036-43-5
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
1-androstene-3,17-dione + acceptor
1,4-androstadiene-3,17-dione + reduced reduced acceptor
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH + H+
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
show the reaction diagram
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-
-
-
?
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
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone
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-
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
dihydrotestosterone + NADP+
testosterone + NADPH + H+
show the reaction diagram
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the enzyme performs conversion of testosterone to dihydrotestosterone
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-
r
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
show the reaction diagram
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-
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(10bR)-8-chloro-4,10b-dimethyl-1,4,6,10b-tetrahydrobenzo[f]quinoline-3(2H)-thione
13.2% inhibition at 0.04 mM
(10bR)-8-chloro-4,10b-dimethyl-1,5,6,10b-tetrahydrophenanthridin-3(2H)-one
-
(10bR)-8-chloro-4,5,10b-trimethyl-1,5,6,10b-tetrahydrophenanthridin-3(2H)-one
-
(10bR)-8-chloro-5,10b-dimethyl-1,5,6,10b-tetrahydrophenanthridin-3(2H)-one
-
(11aR)-7-(1-hydroxypropan-2-yl)-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
weak inhibition
(11aR)-7-(1-hydroxypropan-2-yl)-1,4a,6a-trimethyltetradecahydrocyclopenta[5,6]naphtho[2,1-d][1,3]oxazin-2(1H)-one
weak inhibition
(11aR)-7-(1-hydroxypropan-2-yl)-1,4a,6a-trimethyltetradecahydrocyclopenta[5,6]naphtho[2,1-d][1,3]oxazine-2(1H)-thione
weak inhibition
(11aR)-N,N-diethyl-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
weak inhibition
(16alpha,17beta)-17-hydroxy-16-methylandrost-4-en-3-one
-
(16beta)-16-bromo-3,20-dioxopregna-1,4,6-trien-17-yl cyclopentylacetate
-
(16beta)-16-methyl-3,20-dioxopregna-1,4,6-trien-17-yl acetate
-
(16beta)-16-methyl-3,20-dioxopregna-1,4,6-trien-17-yl cyclopentylacetate
-
(16beta)-16-methyl-3,20-dioxopregna-1,4,6-trien-17-yl pentanoate
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(16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl cyclopentylacetate
-
(16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl cyclopropanecarboxylate
-
(16beta)-16-methylandrost-4-ene-3,17-dione
-
(16beta)-17-hydroxy-16-methylpregna-1,4,6-triene-3,20-dione
-
(16beta)-6-bromo-16-methyl-3,20-dioxopregna-4,6-dien-17-yl acetate
-
(16beta)-6-bromo-17-(hex-1-en-2-yloxy)-16-methylpregna-4,6-diene-3,20-dione
-
(16beta)-6-chloro-16-methyl-17-[(1-phenylethenyl)oxy]pregna-4,6-diene-3,20-dione
-
(16beta)-6-chloro-16-methyl-3,20-dioxopregna-4,6-dien-17-yl acetate
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(17beta)-16-ethyl-17-hydroxyandrost-4-en-3-one
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(17beta)-17-(2-oxo-3-phenyl-1,3-oxazinan-6-yl)androst-4-en-3-one - 3-phenyl-1,3-oxazinan-2-one (1:1)
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(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4,6,8-pentaene-3-carboxylic acid
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(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4,6-tetraene-3-carboxylic acid
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(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4-triene-3-carboxylic acid
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(17beta)-17-(propan-2-ylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid
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(17beta)-17-[3-(4-bromophenyl)-2-oxo-1,3-oxazinan-6-yl]androst-4-en-3-one
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(17beta)-17-[3-(4-chlorophenyl)-2-oxo-1,3-oxazinan-6-yl]androst-4-en-3-one
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(17beta)-17-[3-(4-ethoxyphenyl)-2-oxo-1,3-oxazinan-6-yl]androst-4-en-3-one
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(17beta)-17-[3-(4-ethylphenyl)-2-oxo-1,3-oxazinan-6-yl]androst-4-en-3-one
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(17beta)-17-[3-(4-methoxyphenyl)-2-oxo-1,3-oxazinan-6-yl]androst-4-en-3-one
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(17beta)-17-[di(propan-2-yl)carbamoyl]-4-fluoroandrost-3-ene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]-4-methylandrosta-3,5-diene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]-6-fluoroandrosta-3,5-diene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]androst-3-ene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-2,4,6-triene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-3,5,11-triene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-3,5-diene-3-carboxylic acid
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(17beta)-17-[di(propan-2-yl)carbamoyl]estra-3,5-diene-3-carboxylic acid
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(17beta)-2-chloro-17-(propan-2-ylcarbamoyl)estra-1(10),2,4-triene-3-carboxylic acid
-
(17beta)-3-(hydroxymethyl)-N-(propan-2-yl)androsta-3,5-diene-17-carboxamide
weak inhibitor
(17beta)-3-nitro-N-(propan-2-yl)androst-3-ene-17-carboxamide
-
(17beta)-4-bromo-N-tert-butyl-3-oxoandrost-4-ene-17-carboxamide
-
(17beta)-4-fluoro-17-(propan-2-ylcarbamoyl)estra-1(10),2,4-triene-3-carboxylic acid
-
(17beta)-N-tert-butyl-3-oxo-4-sulfanylandrost-4-ene-17-carboxamide
-
(17beta)-N-tert-butyl-4-chloro-3-oxoandrost-4-ene-17-carboxamide
-
(17beta)-N-tert-butyl-4-cyano-3-oxoandrost-4-ene-17-carboxamide
-
(1R,4R,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,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
-
(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
-
(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
-
(1S,9aR,11aR)-1-butyl-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)-1-(cyclohexylacetyl)-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)-6-bromo-9a,11a-dimethyl-7-oxo-N-(tricyclo[3.3.1.13,7]dec-1-yl)-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-bromo-N,N-diethyl-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)-6-chloro-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)-6-chloro-N,N-diethyl-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)-9a,11a-dimethyl-1-nonanoyl-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)-9a,11a-dimethyl-N-(2-methylpropyl)-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-diethyl-5,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N-diethyl-5,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N-diethyl-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
-
(1S,9aR,11aS)-N-(4,4'-di-tert-butylbiphenyl-3-yl)-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
-
(1S,9aR,11aS)-N-(4-tert-butylbiphenyl-3-yl)-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
-
(1S,9aR,11aS)-N-(5-bromo-2-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
-
(1S,9aR,11aS)-N-(dicyclohexylmethyl)-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
-
(1S,9aR,11aS)-N-(diphenylmethyl)-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-(diphenylmethyl)-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
-
(1S,9aR,11aS)-N-tert-butyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-[1-(4-chlorophenyl)cyclobutyl]-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
-
(1S,9aR,11aS)-N-[2,5-bis(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
-
(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
-
(1S,9aR,11aS)-N-[bis(4-chlorophenyl)methyl]-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
-
(1S,9aS,11aS)-N,N-diethyl-8,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(20E)-20-(hydroxyimino)pregn-4-en-3-one
-
(20E)-20-(hydroxyimino)pregn-4-ene-3,6-dione
-
(20E)-20-(hydroxyimino)pregna-4,14,16-trien-3-one
-
(20E)-20-(hydroxyimino)pregna-4,16-dien-3-one
-
(21E)-21-(hydroxyimino)pregn-4-en-3-one
-
(22R,S)-N-(1,1,1-trifluoro-2-phenylprop-2-yl)-3-oxo-4-aza-5-androst-1-ene-17-carboxamide
i.e. FCE 28260
(2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,10a,10b,11,12,12a-dodecahydrochrysen-2-yl acetate
-
(2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl (2-fluorophenyl)acetate
-
(2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl acetate
-
(2R,3R,10aR,12aS)-2-hydroxy-2,10a,12a-trimethyl-3-phenyl-3,4,4a,10a,10b,11,12,12a-octahydrochrysene-1,8(2H,4bH)-dione
-
(2R,3R,10aR,12aS)-2-hydroxy-2,10a,12a-trimethyl-3-phenyl-3,4,4a,9,10,10a,10b,11,12,12a-decahydrochrysene-1,8(2H,4bH)-dione
-
(3beta)-6,20-dioxopregna-4,16-dien-3-yl 3-bromopropanoate
-
(3beta)-6,20-dioxopregna-4,16-dien-3-yl 3-chloropropanoate
-
(3beta)-6,20-dioxopregna-4,16-dien-3-yl 3-iodopropanoate
-
(3beta)-6,20-dioxopregna-4,16-dien-3-yl propanoate
-
(3E,4aR,6aS,7S,11aR)-N,N-diethyl-3-(hydroxymethylidene)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4-[[1-(dicyclohexylacetyl)piperidin-4-ylidene]methyl]-3-fluorophenyl)acetic acid
-
(4-[[1-(dicyclohexylacetyl)piperidin-4-ylidene]methyl]phenyl)acetic acid
-
(4aR,10bR)-4,10b-dimethyl-8-[(E)-2-phenylethenyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-4,8-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-(furan-2-yl)-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-bromo-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinoline-3(2H)-thione
21.6% inhibition at 0.04 mM
(4aR,10bR)-8-chloro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
i.e. LY191704
(4aR,10bR)-8-fluoro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,10bR)-8-[(E)-2-(isoquinolin-4-yl)ethenyl]-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
(4aR,5S,6aS,11aR)-N-(diphenylmethyl)-5-hydroxy-1,4a,6a,10-tetramethyl-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
-
(4aR,5S,6aS,11aR)-N-(diphenylmethyl)-5-hydroxy-4a,6a,10-trimethyl-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
-
(4aR,6aR)-1,4a,6a,10-tetramethyl-7-(6-methylheptan-2-yl)-1,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aR)-1,4a,6a,10-tetramethyl-7-(6-methylheptan-2-yl)-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aR)-1,4a,6a-trimethyl-7-(6-methylheptan-2-yl)-10-propyl-1,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aR)-1,4a,6a-trimethyl-7-(6-methylheptan-2-yl)hexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aR)-10-ethyl-1,4a,6a-trimethyl-7-(6-methylheptan-2-yl)hexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aR)-4a,6a,10-trimethyl-7-(6-methylheptan-2-yl)-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aS,11aR)-1,4a,6a,10-tetramethyl-2-oxo-N-(4,4,4-trifluoro-2-methyl-3-oxobutan-2-yl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,11aR)-1,4a,6a,10-tetramethyl-2-oxo-N-(4,4,4-trifluoro-3-oxobutan-2-yl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,11aR)-1,4a,6a,10-tetramethyl-N-(2-methyl-4-oxopentan-3-yl)-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
-
(4aR,6aS,11aR)-N-(2-cyanopropan-2-yl)-1,4a,6a,10-tetramethyl-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
-
(4aR,6aS,7E,11aR)-7-(chloromethylidene)-1,6a-dimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
i.e. azaestranone II
(4aR,6aS,7S)-1,4a,6a-trimethyl-2,5-dioxo-N-phenyl-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-1,4a,6a-trimethyl-2,5-dioxo-N-phenylhexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-1,4a,6a-trimethyl-2,5-dioxo-N-[2-(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-4a,6a-dimethyl-2,5-dioxo-N-phenyl-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-4a,6a-dimethyl-2,5-dioxo-N-phenylhexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-N,1,4a,6a-tetramethyl-2,5-dioxo-N-phenyl-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-N,4a,6a-trimethyl-2,5-dioxo-N-phenyl-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-N-(2-chlorophenyl)-1,4a,6a-trimethyl-2,5-dioxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S)-N-[2,5-bis(trifluoromethyl)phenyl]-1,4a,6a-trimethyl-2,5-dioxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-1,4a,6a-trimethyl-N-(3-methylbutanoyl)-2-oxo-N-(propan-2-yl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-1,4a,6a-trimethyl-N-(3-methylbutanoyl)-2-oxo-N-(propan-2-yl)hexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-4a,6a-dimethyl-2-oxo-N-(4,4,4-trifluoro-3-oxobutan-2-yl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]isoquinolin-7-ol 2-oxide
-
(4aR,6aS,7S,11aR)-4a,6a-dimethyl-N-(3-methylbutanoyl)-2-oxo-N-(propan-2-yl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-4a,6a-dimethyl-N-(3-methylbutanoyl)-2-oxo-N-(propan-2-yl)hexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-7-hydroxy-1,4a,6a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aS,7S,11aR)-N-(3,3-dimethylpentanoyl)-1,4a,6a-trimethyl-N-(2-methylbutan-2-yl)-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-N-(diphenylmethyl)-1,4a,6a-trimethyl-2,5-dioxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-N-(diphenylmethyl)-4a,6a-dimethyl-2,5-dioxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-N-(diphenylmethyl)-4a,6a-dimethyl-2,5-dioxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-N-cyclohexyl-N-(cyclohexylacetyl)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
(4aR,6aS,7S,11aR)-N-[2,5-bis(trifluoromethyl)phenyl]-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
-
(4aR,7S)-8-ethyl-4a,7-dimethyl-10-methylidene-7-[(2S)-3-oxobutan-2-yl]-4,4a,4b,5,6,7,8,8a,9,10-decahydrophenanthren-2(3H)-one
-
(4aS,6aS,7S,11aR)-4a,6a-dimethyl-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[5,4-f]isoquinolin-7-ol
-
(4aS,6aS,7S,11aS)-4a,6a-dimethyl-2-oxo-N,N-diphenyl-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinoline-7-carboxamide
-
(4aS,6aS,7S,11aS)-4a,6a-dimethyl-2-oxo-N-phenyl-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinoline-7-carboxamide
-
(4aS,6aS,7S,11aS)-4a,6a-dimethyl-2-oxo-N-[2-(trifluoromethyl)phenyl]-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinoline-7-carboxamide
-
(4aS,6aS,7S,11aS)-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinolin-7-ol 3-oxide
-
(4aS,6aS,7S,11aS)-4a,6a-dimethyl-7-[methyl(phenyl)carbamoyl]-2-oxo-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinolinium
-
(4aS,6aS,7S,11aS)-N,N-di(1H-indol-1-yl)-4a,6a-dimethyl-2-oxo-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinoline-7-carboxamide
-
(4aS,6aS,7S,11aS)-N-(biphenyl-3-yl)-4a,6a-dimethyl-2-oxo-2,3,4,4a,5,6,6a,7,8,9,9a,10,11,11a-tetradecahydro-1H-indeno[4,5-h]isoquinoline-7-carboxamide
-
(4R)-5,10-seco-19-nor-pregna-4,5-diene-3,10,20-trione
a non-competitive and possibly irreversible inhibitor
(4R)-5,10-seco-estra-4,5-diene-3,10,17-trione
a non-competitive and possibly irreversible inhibitor
(5,20R)-4-diazo-21-hydroxy-20-methyl-pregn-6-en-3-one
i.e. RMI-18,341
(5alpha,6alpha)-20-oxo-5,6-epoxypregn-16-en-3-yl acetate
-
(5alpha17beta)-17-N,N-diethylcarbamoyl-4-methyl-4-aza-5-androstan-3-one
-
(5aR,7aS,8S,12aR)-5a,7a-dimethyl-2-oxooctadecahydrocyclopenta[5,6]naphtho[2,1-b]azepin-8-yl acetate
-
(5aR,9aR,11aS)-1-(3,3-dimethylbutanoyl)-6,9a,11a-trimethyl-1,2,3,3a,3b,4,5,5a,6,9a,9b,10,11,11a-tetradecahydro-7H-indolo[5,4-f]quinolin-7-one
-
(5aR,9aR,11aS)-1-(3,3-dimethylbutanoyl)-6,9a,11a-trimethylhexadecahydro-7H-indolo[5,4-f]quinolin-7-one
-
(5aR,9aR,11aS)-1-(3,3-dimethylbutanoyl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,5a,6,9a,9b,10,11,11a-tetradecahydro-7H-indolo[5,4-f]quinolin-7-one
-
(5aR,9aR,11aS)-1-(3,3-dimethylbutanoyl)-9a,11a-dimethylhexadecahydro-7H-indolo[5,4-f]quinolin-7-one
-
(6aR,7S,9aR,11aS)-7-hydroxy-1,9a,11a-trimethylhexadecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(6aS,10aS,12aS)-1,10a,12a-trimethylhexadecahydronaphtho[2,1-f]quinoline-2,8-dione
-
(6aS,7S)-6a-methyl-N-(propan-2-yl)-5,6,6a,7,8,9,9a,9b-octahydro-4bH-indeno[5,4-f]isoquinoline-7-carboxamide 2-oxide
-
(6aS,7S)-N,N-diethyl-6a-methyl-5,6,6a,7,8,9,9a,9b-octahydro-4bH-indeno[5,4-f]isoquinoline-7-carboxamide 2-oxide
-
(6aS,8S,10aS,12aS)-8-hydroxy-1,10a,12a-trimethylhexadecahydronaphtho[2,1-f]quinolin-2(1H)-one
-
(6beta)-6-bromo-16-methyl-17-[(1-phenylethenyl)oxy]pregna-4,6-diene-3,20-dione
-
(7-chloro-3,4,4a,9-tetrahydrophenanthren-2-yl)phosphinic acid
-
(7aR,9aS,10S)-N,N-diethyl-7a,9a-dimethyl-5-oxo-1,2,3,5,6,7,7a,7b,8,9,9a,10,11,12,12a,12b-hexadecahydrobenzo[b]indeno[5,4-d]azepine-10-carboxamide
-
(7aS,8S,10aS,10bS)-N-tert-butyl-7a-methyl-2-oxo-2,3,4,5a,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[f]pyrido[1,2-a]quinoline-8-carboxamide
-
(7aS,8S,12aR)-7a-methyl-8-(phenylamino)-5a,6,7,7a,8,9,10,10a,10b,11,12,12a-dodecahydrocyclopenta[f]pyrido[1,2-a]quinolin-2(1H)-one
-
(7aS,8S,12aR)-8-[benzyl(phenyl)amino]-7a-methyl-5a,6,7,7a,8,9,10,10a,10b,11,12,12a-dodecahydrocyclopenta[f]pyrido[1,2-a]quinolin-2(1H)-one
-
(8a,9b,10x,14x)-N-tert-butyl-3-oxoestr-4-ene-17-carboxamide
-
(8R,9aS,11aS)-1,9a,11a-trimethyl-2-oxo-N,N-di(propan-2-yl)hexadecahydro-1H-indeno[5,4-f]quinoline-8-carboxamide
-
(9aR,11aS)-1-(3,3-dimethylbutanoyl)-6,9a,11a-trimethyl-1,2,3,3a,3b,4,6,8,9,9a,9b,10,11,11a-tetradecahydro-7H-indolo[5,4-f]quinolin-7-one
-
(S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yl]-butyric acid
-
(S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yl]butyric acid
-
1-(3-carboxypropyl)-4-[4-([[3-(2-methylpropyl)phenyl][4-(2-methylpropyl)phenyl]methyl]amino)benzoyl]-1H-pyrrole-3-carboxylic acid
-
1-cyclopropyl-3-ethyl-1-[(4aR,6aS,7S,11aR)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]urea
20% inhibition at 100 nM in transfected SW-13 cells
1-cyclopropyl-3-methyl-1-[(4aR,6aS,7S,11aR)-1,4a,6a,10-tetramethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]urea
-
1-cyclopropyl-3-phenyl-1-[(4aR,6aS,7S,11aR)-1,4a,6a,10-tetramethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]urea
-
1-cyclopropyl-3-phenyl-1-[(4aR,6aS,7S,11aR)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]urea
1-methyl-5-phenylpiperidin-2-one
13.5% inhibition at 0.04 mM
1-methyl-5-[4-[(E)-2-phenylethenyl]phenyl]piperidin-2-one
-
1-methyl-5-[4-[(E)-phenyldiazenyl]phenyl]piperidin-2-one
-
16,16-dimethylandrost-4-ene-3,17-dione
-
16-ethyl-17beta-hydroxy-4-estren-3-one
i.e. TSAA-291
17-(2-cyclopentylethoxy)-6-methylidenepregn-4-ene-3,20-dione
-
17-(3-cyclopentylpropoxy)-6-methylidenepregn-4-ene-3,20-dione
-
17-hydroxy-6-methylidenepregn-4-ene-3,20-dione
-
17-hydroxyestra-4,8-dien-3-one
-
17-hydroxyestra-4,9(11)-dien-3-one
-
17beta-(N-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one
-
17beta-N,N-diethylcarbamoyl-4-methyl-4-aza-5alpha-androstan-3-one
-
17beta-N-(2,5-bis(trifluoromethyl)-phenyl)-3-oxo-4-aza-5alpha-androst-1-ene-17-carboxamide
-
2',3'-tetrahydrofuran-2'-spiro-17-(6-methylene-4-androsten-3-one)
i.e. L612,710
2-(trifluoromethyl)phenyl 4-methyl-3-oxo-2,3,5,6-tetrahydro-1H-pyrido[1,2-a]quinoline-8-carboxylate
368% inhibition at 0.01 mM
2-fluorophenyl 4-methyl-3-oxo-2,3,5,6-tetrahydro-1H-pyrido[1,2-a]quinoline-8-carboxylate
166% inhibition at 0.01 mM
2-methyl-N-phenyl-N-[(4aR,6aS,7S,11aR)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinolin-7-yl]propanamide
-
2-oxo-8-(prop-2-en-1-yl)-2H-chromen-7-yl benzoate
-
20-oxo-16,17-epoxypregn-5-en-3-yl acetate
-
3,20-dioxopregn-4-en-17-yl (4-bromophenyl)carbamate
-
3,20-dioxopregn-4-en-17-yl phenylcarbamate
-