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Information on EC 1.3.99.5 - 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor)
for references in articles please use BRENDA:EC1.3.99.5
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EC Tree 1 Oxidoreductases
1.3 Acting on the CH-CH group of donors
1.3.99 With unknown physiological acceptors
1.3.99.5 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor)
IUBMB Comments
A flavoprotein. This bacterial enzyme, characterized from Comamonas testosteroni, is involved in androsterone degradation. cf. EC 1.3.1.22, 3-oxo-5α-steroid 4-dehydrogenase (NADP+).
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 1.3.99.5
- androgen
- prostate
- dihydrotestosterone
- finasteride
- hyperplasia
- progesterone
- aromatase
-
steroidogenic
-
castrated
- dutasteride
-
neurosteroids
- genitalia
- alopecia
- 5alpha-dihydrotestosterone
- androstenedione
-
antiandrogenic
-
17beta-hydroxysteroid
- hypospadias
-
gabaa
- allopregnanolone
- 17beta-hsd
-
masculinization
-
androgenetic
-
tamsulosin
-
virilization
-
androgen-dependent
- cyp17a1
-
3alpha-hydroxysteroid
- hsd17b3
-
neuroactive
- pseudohermaphroditism
-
alpha-blocker
-
prostate-specific
- libido
-
bald
-
alpha1-adrenoceptors
-
bothersome
-
intraprostatic
-
micropenis
-
terazosin
-
doxazosin
- androstanediols
-
gonadectomized
-
urologist
-
3alpha
- hirsutism
- 3alpha-hsd
- androsterone
- medicine
- hsd3b1
- akr1c3
Reaction Schemes
showSynonyms
5alpha-reductase, srd5a2, srd5a1, 5alpha-r, steroid 5alpha-reductase, 5alpha-reductase type 2, 5alpha-reductase type 1, 5alphar1, 5alpha reductase, 5alphar2, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-keto-DELTA4-steroid-5 alpha-reductase
-
-
-
-
3-ketosteroid-DELTA4(5alpha)-dehydrogenase
-
-
-
-
3-oxo-5alpha-steroid DELTA4-dehydrogenase
-
-
-
-
3-oxo-steroid-4-ene dehydrogenase
3-oxosteroid DELTA4-dehydrogenase
-
-
-
-
4-ene-3-ketosteroid-5alpha-oxidoreductase
-
-
-
-
5 alpha-SR2
-
-
-
-
5-alpha reductase II
5alpha-R
5alpha-reductase
5alphaR1
5alphaR2
dehydrogenase, 3-oxo-5alphasteroid DELTA4-
-
-
-
-
DELTA4(5alpha)DH
-
-
-
-
DELTA4-3-keto steroid 5alpha-reductase
-
-
-
-
DELTA4-3-ketosteroid 5alpha-oxidoreductase
-
-
-
-
DELTA4-3-oxo steroid reductase
-
-
-
-
DELTA4-3-oxosteroid-5alpha-reductase
-
-
-
-
DELTA4-5alpha-dehydrogenase
-
-
-
-
S5AR
-
-
-
-
SRD5A2
SRD5alpha
steroid 5alpha-reductase
steroid 5alpha-reductase type 1
steroid 5alpha-reductase type 2
steroid DELTA4-5alpha-reductase
-
-
-
-
steroid-5alpha-reductase
testosterone 5alpha-reductase
-
-
-
-
type 2 5alpha-reductase
steroid 5alpha-reductase
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-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 3-oxo-5alpha-steroid + acceptor = a 3-oxo-DELTA4-steroid + reduced acceptor
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
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redox reaction
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-
-
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reduction
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-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
androstenedione degradation II (anaerobic), testosterone and androsterone degradation to androstendione (aerobic)
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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+).
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CAS REGISTRY NUMBER
COMMENTARY
9036-43-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(5alpha)-androst-1-en-3,17-dione + oxidized dichlorophenolindophenol
1,4-androstadiene-3,17-dione + reduced dichlorophenolindophenol
Substrates: -
Products: -
Products: -
?
1-androstene-3,17-dione + acceptor
1,4-androstadiene-3,17-dione + reduced reduced acceptor
-
Substrates: -
Products: -
Products: -
?
1-androstene-3,17-dione + phenazine methosulfate
1,4-androstadiene-3,17-dione + reduced phenazine methosulfate
1-estrene-3,17-dione + phenazine methosulfate
1,4-estradiene-3,17-dione + reduced phenazine methosulfate
-
Substrates: -
Products: -
Products: -
ir
5alpha-1-androsten-3,17-dione + acceptor
? + reduced acceptor
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Substrates: acceptor: N,N,NĀ,NĀ-tetramethyl-1,4-phenylenediamine, menadione, phenazine methosulfate, cytochrome c
Products: -
Products: -
ir
5alpha-androstane-3,17-dione + N,N,N',N'-tetramethyl-1,4-phenylendiamine
androst-4-ene-3,17-dione + reduced N,N,N',N'-tetramethyl-1,4-phenylendiamine
-
Substrates: -
Products: -
Products: -
r
deoxycorticosterone + reduced acceptor
21-hydroxy-5alpha-pregnan-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
progesterone + reduced acceptor
5alpha-pregnan-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
progesterone + reduced acceptor
pregnane-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + NADPH + H+
dihydrotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
1-androstene-3,17-dione + phenazine methosulfate
1,4-androstadiene-3,17-dione + reduced phenazine methosulfate
-
Substrates: -
Products: -
Products: -
ir
1-androstene-3,17-dione + phenazine methosulfate
1,4-androstadiene-3,17-dione + reduced phenazine methosulfate
-
Substrates: acceptor: N,N,NĀ,NĀ-tetramethyl-1,4-phenylenediamine, menadione, phenazine methosulfate, cytochrome c
Products: -
Products: -
ir
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: 5alpha-reductase converts testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: -
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
5alpha-pregn-3,20-dione + NADP+
progesterone + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
5alpha-pregn-3,20-dione + NADP+
progesterone + NADPH + H+
-
Substrates: 5alpha-reductase also can act on progesterone, which is metabolized to an intermediate product that is then converted to allopregnanolone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to dihydrotestosterone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: -
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: the isoenzyme efficiently catalyzes the in vitro transformation of testosterone into dihydrotestosterone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to dihydrotestosterone
Products: -
Products: -
r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: key enzyme in the degradation of steroids having an A:B ring fusion in a trans configuration
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: 5alpha-dihydrotestosterone is a more potent androgen
Products: 5alpha-dihydrotestosterone is a more potent androgen
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: testosterone i.e. 17beta-hydroxyandrost-4-en-3-one
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: enzyme plays a key role in androgen-dependent target tissues, where it catalyzes the conversion of testosterone to the biologically active dihydrotestosterone, transcriptional control of 5alpha-reductase expression
Products: -
Products: -
?
additional information
?
-
-
Substrates: neonatal testicular androgens, e.g. testosterone, irreversibly program several hepatic enzyme activities in the rat including 5alpha-reductase, tissue-specific physiological regulation of isozymes
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme produces precursors for the biosynthesis of allopregnenolone and tetrahydrodeoxycorticosterone, physiological role of the isozymes in the brain, overview
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5alpha-pregn-3,20-dione + NADP+
progesterone + NADPH + H+
-
Substrates: 5alpha-reductase also can act on progesterone, which is metabolized to an intermediate product that is then converted to allopregnanolone
Products: -
Products: -
r
deoxycorticosterone + reduced acceptor
21-hydroxy-5alpha-pregnan-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
progesterone + reduced acceptor
5alpha-pregnan-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
progesterone + reduced acceptor
pregnane-3,20-dione + acceptor
-
Substrates: -
Products: -
Products: -
?
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: 5alpha-reductase converts testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to dihydrotestosterone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
Substrates: the isoenzyme efficiently catalyzes the in vitro transformation of testosterone into dihydrotestosterone
Products: -
Products: -
r
dihydrotestosterone + NADP+
testosterone + NADPH + H+
-
Substrates: the enzyme performs conversion of testosterone to dihydrotestosterone
Products: -
Products: -
r
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: key enzyme in the degradation of steroids having an A:B ring fusion in a trans configuration
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: -
Products: -
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: -
Products: 5alpha-dihydrotestosterone is a more potent androgen
Products: 5alpha-dihydrotestosterone is a more potent androgen
?
testosterone + reduced acceptor
5alpha-dihydrotestosterone + acceptor
-
Substrates: enzyme plays a key role in androgen-dependent target tissues, where it catalyzes the conversion of testosterone to the biologically active dihydrotestosterone, transcriptional control of 5alpha-reductase expression
Products: -
Products: -
?
additional information
?
-
-
Substrates: neonatal testicular androgens, e.g. testosterone, irreversibly program several hepatic enzyme activities in the rat including 5alpha-reductase, tissue-specific physiological regulation of isozymes
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme produces precursors for the biosynthesis of allopregnenolone and tetrahydrodeoxycorticosterone, physiological role of the isozymes in the brain, overview
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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; 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; 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; weak inhibition
(11aR)-N,N-diethyl-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
weak inhibition; weak inhibition
(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 cyclopentylacetate
-
(16beta)-16-methyl-3,20-dioxopregna-1,4,6-trien-17-yl pentanoate
-
(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)-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
-
(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)
-
(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4,6,8-pentaene-3-carboxylic acid
-
(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4,6-tetraene-3-carboxylic acid
-
(17beta)-17-(propan-2-ylcarbamoyl)estra-1(10),2,4-triene-3-carboxylic acid
-
(17beta)-17-(propan-2-ylcarbamoyl)estra-1,3,5(10)-triene-3-sulfonic acid
-
(17beta)-17-[(5S)-2-(2-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[(5S)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[(5S)-2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[(5S)-2-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[(5S)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[(5S)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
-
(17beta)-17-[di(propan-2-yl)carbamoyl]-4-fluoroandrost-3-ene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]-4-methylandrosta-3,5-diene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]-6-fluoroandrosta-3,5-diene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]androst-3-ene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-2,4,6-triene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-3,5,11-triene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]androsta-3,5-diene-3-carboxylic acid
-
(17beta)-17-[di(propan-2-yl)carbamoyl]estra-3,5-diene-3-carboxylic acid
-
(17beta)-2-chloro-17-(propan-2-ylcarbamoyl)estra-1(10),2,4-triene-3-carboxylic acid
-
(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
-
(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
-
(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
-
(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
-
(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
-
(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
-
(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
-
(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
-
(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
-
(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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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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(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
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(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
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(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; 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
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(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 (3-fluorophenyl)acetate
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(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
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(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 phenylacetate
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(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
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(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
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(2S,9aR,11aR)-2-(4-chlorophenoxy)-5,9a,11a-trimethyl-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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(3E,4aR,6aS,7S,11aR)-N,N-diethyl-3-(hydroxymethylidene)-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
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(4-[4-(4-bromophenoxy)benzoyl]phenyl)acetic acid
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pH 5.5, 55% inhibition at 0.01 mM, pH 6.6, 59% inhibition at 0.01 mM
(4-[[1-(dicyclohexylacetyl)piperidin-4-ylidene]methyl]-3-fluorophenyl)acetic acid
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(4-[[1-(dicyclohexylacetyl)piperidin-4-ylidene]methyl]phenyl)acetic acid
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(4aR,10bR)-4,10b-dimethyl-8-[(E)-2-phenylethenyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-4,8-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-8-(furan-2-yl)-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-8-bromo-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(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; i.e. LY191704
(4aR,10bR)-8-fluoro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(4aR,10bR)-8-[(E)-2-(isoquinolin-4-yl)ethenyl]-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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(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
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(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
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(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
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(4aR,6aR)-1,4a,6a-trimethyl-7-(6-methylheptan-2-yl)hexadecahydro-2H-indeno[5,4-f]quinolin-2-one
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(4aR,6aR)-10-ethyl-1,4a,6a-trimethyl-7-(6-methylheptan-2-yl)hexadecahydro-2H-indeno[5,4-f]quinolin-2-one
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