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Information on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) and Organism(s) Homo sapiens and UniProt Accession P31213

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IUBMB Comments
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
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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: Eukaryota, Bacteria
Synonyms
5alphar, 5 alpha-reductase type 2, 5alpha-reductase 1, 5alpha-r2, steroid 5-alpha reductase, steroid 5-alpha-reductase, 5-alpha-reductase type 2, 5 alpha-r2, 5-alpha-reductase type 1, steroid 5alpha-reductase type ii, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5alpha-reductase type 2
-
5alpha-SR2
-
steroid 5-alpha-reductase
-
steroid 5alpha-reductase type II
-
type II 5alpha-reductase
-
3-oxosteroid 5alpha-reductase
-
-
-
-
3-oxosteroid DELTA4-dehydrogenase
-
-
-
-
4-ene-3-oxosteroid 5alpha-reductase
-
-
-
-
4-ene-5alpha-reductase
-
-
-
-
5 alpha-R2
-
-
5 alpha-reductase type 2
-
-
5-alpha reductase I
-
isozyme
5-alpha reductase II
-
isozyme
5-alpha-reductase type 1
-
isozyme
5-alpha-reductase type 2
5a-reductase type 1
-
-
5a-reductase type 2
-
-
5alpha-R1
-
-
5alpha-R2
-
-
5alpha-reductase 1
-
-
5alpha-reductase II
-
-
5alpha-reductase type 1
5alpha-reductase type 2
5alphaR
-
-
5alphaR type 2
-
-
cholest-4-en-3-one 5alpha-reductase
-
-
-
-
cortisone alpha-reductase
-
-
-
-
cortisone DELTA 4-5alphareductase
-
-
-
-
DELTA4-3-ketosteroid 5alpha-oxidoreductase
-
-
-
-
DELTA4-3-ketosteroid reductase (5alpha)
-
-
-
-
DELTA4-3-oxosteroid-5 alpha-reductase
-
-
-
-
DELTA4-5alpha-reductase
-
-
-
-
DELTA4-steroid 5alpha-reductase (progesterone)
-
-
-
-
microsomal steroid reductase (5alpha)
-
-
-
-
NADPH:DELTA4-3-oxosteroid-5alpha-oxidoreductase
-
-
-
-
progesterone 5alpha-reductase
-
-
-
-
reduced nicotinamide adenine dinucleotide phosphate:DELTA4-3-ketosteroid 5alpha-oxidoreductase
-
-
-
-
reductase, cholestenone 5alpha-
-
-
-
-
reductase, cortisone DELTA: 4-5alpha-
-
-
-
-
reductase, progesterone 5alpha-
-
-
-
-
S5alphaR
-
-
SRD5A1
SRDA1
-
-
steroid 5-alpha reductase
-
-
steroid 5-alpha-reductase
steroid 5alpha reductase type 2
-
-
steroid 5alpha-hydrogenase
-
-
-
-
steroid 5alpha-reductase
testosterone 5alpha-reductase
-
-
-
-
testosterone delta4-5alpha-reductase
-
-
-
-
testosterone delta4-hydrogenase
-
-
-
-
type 1 5alpha-reductase
type 1 5alphaR
-
-
type 1 SR
-
-
type 1 steroid 5alpha reductase
-
-
type 2 5alpha-reductase
type 2 5alphaR
-
-
type 2 SR
-
-
type 2 steroid 5alpha reductase
-
-
type-1 5alpha-reductase
-
-
type-2 5alpha-reductase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
3-oxo-5alpha-steroid:NADP+ DELTA4-oxidoreductase
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
CAS REGISTRY NUMBER
COMMENTARY hide
37255-34-8
-
72412-84-1
-
9029-09-8
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11alpha-hydroxyprogesterone + NADPH + H+
11alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
11beta,17alpha-dihydroxyprogesterone + NADPH + H+
11beta,17alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
11beta-hydroxyprogesterone + NADPH + H+
11beta-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
11alpha-hydroxyprogesterone + NADPH + H+
11alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
11beta,17alpha-dihydroxyprogesterone + NADPH + H+
11beta,17alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
11beta-hydroxyprogesterone + NADPH + H+
11beta-hydroxydihydroprogesterone + NADP+
show the reaction diagram
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
show the reaction diagram
-
-
-
-
?
3-keto-delta4-abiraterone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
-
-
-
-
?
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
show the reaction diagram
-
-
-
-
r
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
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
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
the enzyme performs conversion of testosterone to dihydrotestosterone
-
-
r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 100% inhibition
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 99% inhibition
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 100% inhibition
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 99% inhibition
2,6,4'-methoxybenzophenone
from Anemarrhena aspholoides rhizomes
3-keto-Delta4-abiraterone
-
-
cis-hinokiresinol
from Anemarrhena aspholoides rhizomes
dutasteride
-
finasteride
mangiferin
a 1,3,6,7-tetrahydroxyxanthone-C2-beta-D-glucoside, from Anemarrhena aspholoides rhizomes, directly inhibits SRD5A2 binding to a complex of enzyme and substrate
(+/-)-LY191704
-
i.e. (4aS,10aR)-7-chloro-1-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-2(1H)-one, non-steroidal, most potent benzoquinoline mimicing 4-azasteroid inhibitors, and specific for isozyme 5alphaR-1, IC50 is 30 nM
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 49% inhibition at 0.02 mM
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 57% inhibition at 0.029 mM
(10bR)-8-chloro-5,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 42% inhibition at 0.03 mM
(1E,4E,6E)-1,7-bis(3-hydroxy-4-methoxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-bis(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(2-chlorophenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(3-hydroxy-4-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(3-nitrophenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(4-methoxyphenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-7-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-7-[3-(cycloprop-2-en-1-yloxy)phenyl]-1-(2-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
-
-
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
-
-
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-naphthylylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.00134 mM
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-phenylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.0014 mM
(4aS,10bS)-4,8-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 11 nM
(4aS,10bS)-8-(2-furyl)-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 59 nM, isoform II, 50% inhibition above 10 nM
(4aS,10bS)-8-bromo-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 60 nM
(4aS,10bS)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 17 nM
(4aS,10bS)-8-chloro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 8 nM, isoform II, 50% inhibition above 0.01 mM
(4aS,10bS)-8-fluoro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-methoxy-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
isoform I, 50% inhibition at 120 nM
(4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one
-
-
(4R)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 312 nM
(4R)-8-chloro-4-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 141 nM
(4S)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 137 nM
(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one
-
-
(6R)-8-chloro-6-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 188 nM
1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 298 nM
1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one
-
61% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
10-azasteroids
-
several
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
-
-
17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
17-diisopropylcarbamoyl-3-androsten-3-carboxyate
-
-
17-diisopropylcarbamoyl-androstan-3-carboxylate
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
-
dead-end inhibition versus testosterone
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
-
-
17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 8.5% inhibition
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 0.4% inhibition
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 32.3% inhibition
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 18.9% inhibition
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
-
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
-
formation of enzyme-NADP+-inhibitor complex
17beta[3-(N-4-bromophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-chlorophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethylphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-methoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-phenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-tolyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
slight inhibition
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
2,5-dihydroxy-1,4-benzoquinone
-
inhibitor isolated from Thai mangrove Avicennia marina
-
2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
43% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
2-(2-(16-(acetylthio)hexadecanamido)ethoxy)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
33% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
2-(2-hydroxypropan-2-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
2-acetyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
2-acetylnaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
2-hydroxy-4-[(4E,6E)-3-oxo-7-phenylhepta-4,6-dien-1-yl]phenyl acetate
-
-
2-methoxy-5-[(6E)-3-methoxy-7-phenylhept-6-en-1-yl]benzene-1,4-diol
-
-
2-propanoylnaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
3-Androstene-3-carboxylic acids
-
-
3-keto-5alpha-abiraterone
-
-
3-keto-Delta4-abiraterone
-
-
3beta-(3'-oxapentanoyloxy)-androst-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
3beta-acetoxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
3beta-hexanoyloxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
4,6,8-trimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.8 nM
4,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 20 nM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
22% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
25% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
56% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl 4-methylpiperazine-1-carboxylate
-
17% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azepane-1-carboxylate
-
70% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azocane-1-carboxylate
-
20% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylethyl)carbamate
-
72% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylpropyl)carbamate
-
22% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibenzylcarbamate
-
51% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibutylcarbamate
-
32% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dimethylcarbamate
-
29% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dipropylcarbamate
-
77% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl morpholine-4-carboxylate
-
15% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl piperidine-1-carboxylate
-
68% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl pyrrolidine-1-carboxylate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-methylethyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-propylbutyl)phenyl diethylcarbamate
-
27% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclobutyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cycloheptyl)phenyl diethylcarbamate
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclopentyl)phenyl diethylcarbamate
-
5% inhibition at 0.01 mM
4-(2-[5-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 310 nM, isoform II, 50% inhibition above 0.1 mM
4-(2-[6-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 62 nM, isoform II, 50% inhibition at 270 nM
4-(3-(4-(N-methylacetamido)phenyl)pentan-3-yl)phenyl dibenzylcarbamate
-
competitive inhibitor
4-(4'-formylphenoxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.007 mM
4-(biphenyl-4'-yloxy)phenylacetic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00006 mM
4-(biphenyl-4'-yloxy)phenylformic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.000006 mM
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0013 mM
4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 10% inhibition at 0.01 mM, BPH tissue, 68% inhibition at 0.01 mM
4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 2% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0078 mM
4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 7% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00043 mM
4-Androsten-3-one-17beta-carboxylic acid
-
competitive
4-azasteroids
4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0047 mM, DU145 cells, 44% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.004 mM, DU145 cells, 16% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 15% inhibition at 0.001 mM, DU145 cells, 9% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00233 mM, DU145 cells, 28% inhibition at 0.001 mM
4-carboxy-4'-(N-adamantyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0019 mM, DU145 cells, 16% inhibition at 0.001 mM
4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 185 nM
4-methyl-4-azasteroids
-
4-methyl-5,6-dihydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 1400 nM
4-methyl-azasteroid
-
-
4-[(6E)-3-oxo-7-phenylhept-6-en-1-yl]phenyl acetate
-
-
4-[1-[4-(acetylamino)-3-methylphenyl]-1-ethylpropyl]-2-methylphenyl diethylcarbamate
-
17% inhibition at 0.01 mM
4-[2-(6-[[bis(4-fluorophenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 50 nM, isoform II, 50% inhibition at 340 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]amino]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 42 nM, isoform II, 50% inhibition at 480 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 130 nM, isoform II, 50% inhibition at 930 nM
4-[3-[(2,2-diphenyl-1,3-benzodioxol-5-yl)oxy]-2-methyl-1H-indol-1-yl]butanoic acid
-
isoform I, 50% inhibition at 10 nM, isoform II, 50% inhibition at 6300 nM
6,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.3 nM
6-azasteroids
-
several
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
8-bromo-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 60 nM, isoform I
8-chloro-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 49 nM
8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 460 nM, isoform I
8-chloro-1-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 204 nM
8-chloro-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 459 nM
8-chloro-4,5-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.6 nM
8-chloro-4,6-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 8.5 nM
8-chloro-4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 7.6 nM
8-chloro-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 30 nM, isoform I
8-chloro-5-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 346 nM
8-chloro-6-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.4 nM
8-fluoro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 600 nM, isoform I
8-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 376 nM
8-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 176 nM
acrylate episteride
-
-
alpha-4-azasteroids
-
substitution of finasteride N-group by 6-azasteroids increased the rate of inhibition of type-1 5-alpha-reductases
avicequinone C
-
inhibitor isolated from Thai mangrove Avicennia marina
-
benzoquilizin-3-ones
-
diverse, mimics of 10-azasteroids, overview, structure-activity relationships
benzoquinolines
-
compounds as mimics of 4-azasteroid inhibitors, diverse, overview, compounds derived from 6-azasteroids, overview
bisdemethoxycurcumin
-
22.2% inhibition at 0.3 mM
curcumin
-
complete inhibition at 0.3 mM
dehydroepiandrosterone
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
demethoxycurcumin
-
complete inhibition at 0.3 mM
deoxycorticosterone acetate
-
competitive
docosanol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
dutasteride
epristeride
-
-
estradiol
-
in female genital skin fibroblasts
estradiol-17beta
-
-
finasteride
FK143
-
i.e. 4-[3-(3-[[bis-(4-isobutyl-phenyl)-methyl]amino]-benzoyl)-indol-1-yl]-butyric acid, a non-steroidal bi-substrate inhibitor
Lapachol
-
inhibitor isolated from Thai mangrove Avicennia marina
lauric acid
-
isoform 1, 50% inhibition at 0.0167 mM, isoform 2, 50% inhibition at 0.0186 mM
lauric acid ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
Lawsone
-
inhibitor isolated from Thai mangrove Avicennia marina
linoleic acid
-
isoform 1, 50% inhibition at 0.013 mM, isoform 2, 50% inhibition at 0.035 mM
LY3