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Information on EC 1.1.1.64 - testosterone 17beta-dehydrogenase (NADP+) and Organism(s) Homo sapiens and UniProt Accession P37058
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1.1.1.64 testosterone 17beta-dehydrogenase (NADP+)IUBMB Comments
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
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Word Map
- 1.1.1.64
- androgen
- testis
- 17beta-hsd3
- androstenedione
- testicular
- leydig
- hsd17b3
-
steroidogenic
-
puberty
-
5alpha-reductase
- pseudohermaphroditism
-
genitalia
-
dehydrogenase-3
- estrone
- p450scc
- medicine
- drug development
- diagnostics
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
17betahsd3, 17beta-hydroxysteroid dehydrogenase 3, 17beta-hsd 3, testosterone 17beta-dehydrogenase (nadp+), 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-ketoreductase
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AKR1C3
NADP-dependent testosterone-17beta-oxidoreductase
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
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-
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oxidation
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reduction
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PATHWAY SOURCE
PATHWAYS
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-, -, -
SYSTEMATIC NAME
IUBMB Comments
17beta-hydroxysteroid:NADP+ 17-oxidoreductase
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
CAS REGISTRY NUMBER
COMMENTARY
9028-63-1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
testosterone + NAD+
androstenedione + NADH
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NAD+ shows 20% of the activity with NADP+
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ir
additional information
?
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human 17beta-hydroxysteroid dehydrogenases are multifunctional enzymes, isozyme 17beta-HSD4 also performs beta-oxidation of branched fatty acids, like pristanic acid, and in bile acid synthesis, e.g. of di- and trihydroxycholestanoic acids, overview
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-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
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the enzyme plays a central role in the development of the male phenotype. Mutations that inactivate the enzyme give rise to a rare form of male pseudohermaphroditism, referred to as 17beta-HSD-3 deficiency
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-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
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convertion of the weak androgen androstendione into the potent androgen testosterone
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-
?
androstenedione + NADPH + H+
testosterone + NADP+
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-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
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the equilibrium state is 92% testosterone to 8% androstenedione
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-
r
androstenedione + NADPH + H+
testosterone + NADP+
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the enzyme is involved in biosynthesis of testosterone
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-
?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
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17beta-hydroxysteroid dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
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17beta-hydroxysteroid dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
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r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
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17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
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r
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
the enzyme plays a central role in the development of the male phenotype. Mutations that inactivate the enzyme give rise to a rare form of male pseudohermaphroditism, referred to as 17beta-HSD-3 deficiency
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
convertion of the weak androgen androstendione into the potent androgen testosterone
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
-
the enzyme is involved in biosynthesis of testosterone
-
-
?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(3alpha,5alpha)-3-[[trans-2,5-dimethyl-4-[[2-(trifluoromethyl)-phenyl]sulfonyl]piperazin-1-yl]methyl]-3-hydroxyandrostan-17-one
strong inhibition of isoform 17beta-HSD3 overexpressed in HEK-293 cells
(3R,5S,8R,9S,10S,13S,14S)-3'-benzyl-10,13-dimethyltetradecahydro-2'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidine]-2',17(2H)-dione
strong inhibition of isoform 17beta-HSD3 overexpressed in HEK-293 cells. 44% inhibition at 0.1 microM in homogenized cells
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
5-(3-bromo-4-hydroxybenzylidene)-3-(4-fluorophenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-bromo-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one
compound demonstrates significant selectivity for isoform 17beta-hydroxysteroid dehydrogenase type 3 over the related isoenzymes and nuclear receptors. IC50 value 14 nM in cell-based assay
5-(3-bromo-4-hydroxybenzylidene)-3-(4-methylphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-(3-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-tioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
strong inhibitory activity on isoform 3beta-HSD3
bis(2-butoxyethyl) phthalate
potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
dicyclohexyl phthalate
potent inhibitor of testis 17beta-hydroxysteroid dehydrogenase type 3, additionally inhibits 3beta-hydroxysteriod dehydrogenase
STX2171
ability to penetrate the cell. Lack of inhibition of 17beta-HSD2 (the enzyme that catalyzes the opposite reaction to that of 17beta-HSD3, which is the oxidation of active testosterone to inactive androstenedione)
(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
93.3% inhibition at 0.1 mM
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
89.1% inhibition at 0.1 mM
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
92.7% inhibition at 0.1 mM
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
93.5% inhibition at 0.1 mM
(3,6-dihydropyridin-1(2H)-yl)(1H-indol-2-yl)methanone
crystal structure analysis of enzyme-inhibitor complex
(3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
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(3R,10S,13S)-3-(Adamantan-1-ylmethyl-butyl-amino)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
IC50: 80 nM
(3R,10S,13S)-3-[(2-Cyclopentyl-ethyl)-morpholin-4-yl-amino]-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
IC50: 74 nM
(3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
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(3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
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(3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-(2-methylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
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(3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
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(3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
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(3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,5'S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
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(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(2-phenylethyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(3-phenylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(4-phenylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-en-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-yn-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(4-phenoxyphenyl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(5-phenoxy-1H-1,2,3-triazol-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-2-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[2-[4-(trifluoromethyl)phenyl]ethyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzene-1-sulfonyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzoyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[2-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethoxy)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[(4-bromophenyl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[([1,1'-biphenyl]-4-yl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[[2,4-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3R,5S,8R,9S,10S,13S,14S)-4'-[[3,5-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
-
(3S)-3-benzyl-4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-1-oxa-4-azaspiro[5.5]undecan-2-one
-
-
(5-methyl-1H-indol-2-yl)(4-propylpiperidin-1-yl)methanone
crystal structure analysis of enzyme-inhibitor complex
(RS)-3(3'-phenylpropoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
-
IC50: 0.0421 mM
1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM
1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM
1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
-
1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4
3-((4-nitronaphthalen-1-yl)amino)benzoic acid
inhibitor nanomolar potency and selective inhibition of isoform AKR1C3 but also acts as an androgen receptor antagonist. It inhibits 5alpha-dihydrotestosterone stimulated androgen receptor reporter gene activity with an IC50 value of 4.7 microM and produces a concentration dependent reduction in androgen receptor levels in prostate cancer cells
3-(17'-oxo-5'alpha-androstan-3'alpha-oxy)propanoic acid
-
0.003 mM, 48% inhibition
3-(4-Bromo-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.0083 mM, reduction of androstenedione
3-(4-Chloro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.0018 mM, reduction of androstenedione
3-(4-Fluoro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
-
IC50: 0.007 mM, reduction of androstenedione
3-cyclohexyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-cyclohexylmethyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hexyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-octyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-phenethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-hydroxy-10,13-dimethyl-3-phenyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
-
-
3-pentyl-2-[[(pyridin-2-yl)methyl]sulfanyl]-7-(pyrrolidine-1-carbonyl)quinazolin-4(3H)-one
crystal structure analysis of enzyme-inhibitor complex
3-phenoxybenzoic acid
inhibitor carboxylic acid binds to the oxyanion site, in which the carboxylate group very closely overlays the acetate molecule found in other AKR1C3 structures and forms hydrogen bonds to the enzyme catalytic residues His117 and Tyr55, as well as to a conserved water network located in and near the SP3 subpocket. The 3-phenoxy ring extends into the SP1 subpocket and makes van der Waals contacts with the aromatic residues Phe306, Phe311 and Tyr319 that line the pocket
3-[(4-nitrophenyl)amino]benzoic acid
94fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
360fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
inhibitor shows 17fold and 30fold selectivity against isoforms AKR1C2 and AKR1C1, respectively, and much higher selectivity against AKR1C4
3alpha,3beta-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one
-
0.003 mM, 53% inhibition
3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 352 nM
3alpha-hexanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 28% inhibition
3alpha-hydroxy-3'-phenyl-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 81 nM
3alpha-hydroxy-3beta-(3'-hydroxypropyl)-5alpha-androstan-17-one
-
0.003 mM, 74% inhibition
3alpha-hydroxy-3beta-(prop-2'-enyl)-5alpha-androstan-17-one
-
0.003 mM, 76% inhibition
3alpha-hydroxy-3beta-octyl-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 147 nM
3alpha-hydroxy-3beta-phenylethyl-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 99 nM
3alpha-hydroxy-3beta-phenylmethyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition, IC50: 57 nM
3alpha-hydroxy-3beta-phenylpropyl-5alpha-androstan-17-one
-
0.003 mM, 97% inhibition
3alpha-hydroxy-3beta-propyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition, IC50: 67 nM
3alpha-methoxy-3beta-(2'-phenylethyl)-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 73 nM
3alpha-methoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 154 nM
3alpha-O-(spirotetrahydrofuran-2-yl)-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
3alpha-propanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 87% inhibition
3beta,3alpha-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3beta-(2'-cyclohexylethyl)-3alpha-methoxy-5alpha-androstan-17-one
-
0.003 mM, 88% inhibition, IC50: 354 nM
3beta-cyclohexyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 97 nM
3beta-cyclohexylethyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 60 nM
3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 87 nM
3beta-hydroxy-3alpha-(3'-hydroxypropyl)-5alpha-androstan-17-one
-
0.003 mM, 17% inhibition
3beta-hydroxy-3alpha-(prop-2'-enyl)-5alpha-androstan-17-one
-
0.003 mM, 36% inhibition
3beta-hydroxy-3alpha-phenylmethyl-5alpha-androstan-17-one
-
0.003 mM, 39% inhibition
3beta-n-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 116 nM
3beta-n-hexyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 100 nM
3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 90% inhibition, IC50: 73 nM
3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 142 nM
4-chloro-N-[(4-chlorophenyl)methyl]-5-nitro-1H-pyrazole-3-carboxamide
crystal structure analysis of enzyme-inhibitor complex
4-nitro-2-([4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl)phenol
crystal structure analysis of enzyme-inhibitor complex
5-(benzenesulfonyl)-2-nitrophenol
crystal structure analysis of enzyme-inhibitor complex
Cyclopropanecarboxylic acid ((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-octyl-amide
-
IC50: 57 nM
Cyclopropanecarboxylic acid cyclohexylmethyl-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-amide
-
IC50: 85 nM
heptanoic acid (1-{1-[(3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-ylmethyl)-carbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-amide
-
IC50: 227 nM
methyl (2R)-2-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-4-methylpentanoate
-
-
methyl (2R)-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl](phenoxy)acetate
-
-
methyl (2S)-2-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-4-methylpentanoate
-
-
methyl (2S)-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl](phenoxy)acetate
-
-
methyl [(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]acetate
-
-
N-Adamantan-1-ylmethyl-N-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-butyramide
-
IC50: 35-57 nM
5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1,3-thiazol-2-one
starting compound for high-throughput screening. IC50 value 570 nM in cell-based assay
5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1,3-thiazol-2-one
selective non-steroidal 17beta-HSD3 inhibitor that does not show any undesired inhibition of estrogen biosynthesis and does not possess the transcriptional activity against any of these nuclear receptors
RM-532-105
the inhibitor RM-532-105 seems to have difficulty penetrating the testis and was found to be concentrated in the testicular capsule, therefore unable to inhibit the 17beta-HSD3 located inside the testis
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
-
IC50: 0.0091 mM, reduction of androstenedione
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
-
IC50: 0.00915 mM
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
250fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
in complex with AKR1C3. Compound adopts a similar binding orientation as flufenamic acid, however, its phenylamino ring projects deeper into a subpocket and confers selectivity over the other AKR1C isoforms
Stylopine
the most potent inhibitor among the tested compounds that exhibited moderate selectivity towards AKR1C3 versus AKR1C1, EC 1.1.1.62. Stylopine significantly inhibits the AKR1C3-mediated reduction of daunorubicin in intact cells without considerable cytotoxic effects
additional information
crystal structures of complexes of 17beta-HSD5 with structurally diverse inhibitors derived from high-throughput inhibitor screening, overview. Analysis of interactions between 17beta-HSD5 and inhibitors at the atomic level which enable structure-based drug design for anti-CRPC therapy
-
additional information
-
design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3, structure-activity relationship study, overview
-
additional information
nineteen isoquinoline alkaloids were examined for their ability to inhibit a recombinant AKR1C3 enzyme
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0015
testosterone
-
enzyme activity in cell-free homogenate, approximate value
additional information
additional information
-
the KM-values for R80 mutant enzymes are higher than the Km-value of the wild-type enzyme: for R80K 3.5fold, for R80L 21.6fold, for R80M 90.7fold, for R80Q 61.5fold, for R80Y 61.5fold, for R80Y 85.1fold, for R80I 80fold
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000107
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
pH 7.0, temperature not specified in the publication
0.00273
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
pH 7.0, temperature not specified in the publication
0.017
bis(2-butoxyethyl) phthalate
isoform 17beta-hydroxysteroid dehydrogenase type 3 , pH 7.4, 37°C
0.0335
bis(2-butoxyethyl) phthalate
isoform 3beta-hydroxysteriod dehydrogenase , pH 7.4, 37°C
0.0055
dicyclohexyl phthalate
isoform 17beta-hydroxysteroid dehydrogenase type 3, pH 7.4, 37°C
0.0219
dicyclohexyl phthalate
isoform 3beta-hydroxysteriod dehydrogenase, pH 7.4, 37°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000006
(3alpha,5alpha)-3-[[trans-2,5-dimethyl-4-[[2-(trifluoromethyl)-phenyl]sulfonyl]piperazin-1-yl]methyl]-3-hydroxyandrostan-17-one
Homo sapiens
assay uses homogenized cells, pH not specified in the publication, temperature not specified in the publication
0.000002
5-(3-bromo-4-hydroxybenzylidene)-3-(4-fluorophenyl)-2-thioxo-1,3-oxazolidin-4-one
Homo sapiens
cell-based assay, pH not specified in the publication, temperature not specified in the publication
0.000002
5-(3-bromo-4-hydroxybenzylidene)-3-(4-methylphenyl)-2-thioxo-1,3-oxazolidin-4-one
Homo sapiens
cell-based assay, pH not specified in the publication, temperature not specified in the publication
0.000002
5-(3-chloro-5-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
Homo sapiens
cell-based assay, pH not specified in the publication, temperature not specified in the publication
0.000002
5-(3-fluoro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-2-tioxo-1,3-oxazolidin-4-one
Homo sapiens
cell-based assay, pH not specified in the publication, temperature not specified in the publication
0.000001
5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
Homo sapiens
cell-based assay, pH not specified in the publication, temperature not specified in the publication
0.0136
(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0136
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0134
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0058
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0028
(3,6-dihydropyridin-1(2H)-yl)(1H-indol-2-yl)methanone
Homo sapiens
pH 6.0, 22°C
0.00008
(3R,10S,13S)-3-(Adamantan-1-ylmethyl-butyl-amino)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
Homo sapiens
-
IC50: 80 nM
0.000074
(3R,10S,13S)-3-[(2-Cyclopentyl-ethyl)-morpholin-4-yl-amino]-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
Homo sapiens
-
IC50: 74 nM
0.000037
(5-methyl-1H-indol-2-yl)(4-propylpiperidin-1-yl)methanone
Homo sapiens
pH 6.0, 22°C
0.0091 - 0.00915
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
0.0421
(RS)-3(3'-phenylpropoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
Homo sapiens
-
IC50: 0.0421 mM
0.000094
1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000056
1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000052
1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0027
2,5-diphenyl-p-benzoquinone
Homo sapiens
-
IC50: 0.0027 mM, reduction of androstenedione
0.000213
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
Homo sapiens
pH 7.0, temperature not specified in the publication
0.0052
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
Homo sapiens
pH 7.0, temperature not specified in the publication
0.00084
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
Homo sapiens
pH 7.0, temperature not specified in the publication
0.08
3-((4-nitronaphthalen-1-yl)amino)benzoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.0083
3-(4-Bromo-2-methyl-benzyl)-7-hydroxy-chroman-4-one
Homo sapiens
-
IC50: 0.0083 mM, reduction of androstenedione
0.0018
3-(4-Chloro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
Homo sapiens
-
IC50: 0.0018 mM, reduction of androstenedione
0.007
3-(4-Fluoro-2-methyl-benzyl)-7-hydroxy-chroman-4-one
Homo sapiens
-
IC50: 0.007 mM, reduction of androstenedione
0.0029
3-pentyl-2-[[(pyridin-2-yl)methyl]sulfanyl]-7-(pyrrolidine-1-carbonyl)quinazolin-4(3H)-one
Homo sapiens
pH 6.0, 22°C
0.000036
3-[(4-nitrophenyl)amino]benzoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000054
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000062
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.00546
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
Homo sapiens
pH 7.0, temperature not specified in the publication
0.000352
3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 92% inhibition, IC50: 352 nM
0.000081
3alpha-hydroxy-3'-phenyl-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 95% inhibition, IC50: 81 nM
0.000147
3alpha-hydroxy-3beta-octyl-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 92% inhibition, IC50: 147 nM
0.000099
3alpha-hydroxy-3beta-phenylethyl-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 93% inhibition, IC50: 99 nM
0.000057
3alpha-hydroxy-3beta-phenylmethyl-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 94% inhibition, IC50: 57 nM
0.000067
3alpha-hydroxy-3beta-propyl-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 94% inhibition, IC50: 67 nM
0.000073
3alpha-methoxy-3beta-(2'-phenylethyl)-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 95% inhibition, IC50: 73 nM
0.000154
3alpha-methoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 93% inhibition, IC50: 154 nM
0.000354
3beta-(2'-cyclohexylethyl)-3alpha-methoxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 88% inhibition, IC50: 354 nM
0.000097
3beta-cyclohexyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 95% inhibition, IC50: 97 nM
0.00006
3beta-cyclohexylethyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 93% inhibition, IC50: 60 nM
0.000087
3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 95% inhibition, IC50: 87 nM
0.000116
3beta-n-butyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 92% inhibition, IC50: 116 nM
0.0001
3beta-n-hexyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 95% inhibition, IC50: 100 nM
0.000073
3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 90% inhibition, IC50: 73 nM
0.000142
3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 93% inhibition, IC50: 142 nM
0.0026
4-chloro-N-[(4-chlorophenyl)methyl]-5-nitro-1H-pyrazole-3-carboxamide
Homo sapiens
pH 6.0, 22°C
0.00049
4-nitro-2-([4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl)phenol
Homo sapiens
pH 6.0, 22°C
0.0019
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
Homo sapiens
pH 7.0, temperature not specified in the publication
0.0022
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
Homo sapiens
pH 7.0, temperature not specified in the publication
0.000057
Cyclopropanecarboxylic acid ((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-octyl-amide
Homo sapiens
-
IC50: 57 nM
0.000085
Cyclopropanecarboxylic acid cyclohexylmethyl-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-amide
Homo sapiens
-
IC50: 85 nM
0.000227
heptanoic acid (1-{1-[(3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-ylmethyl)-carbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-amide
Homo sapiens
-
IC50: 227 nM
0.000035 - 0.000057
N-Adamantan-1-ylmethyl-N-((3R,10S,13S)-3-hydroxy-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-butyramide
Homo sapiens
-
IC50: 35-57 nM
0.0233
bis(2-butoxyethyl) phthalate
Homo sapiens
isoform 17beta-hydroxysteroid dehydrogenase type 3 , pH 7.4, 37°C
0.0503
bis(2-butoxyethyl) phthalate
Homo sapiens
isoform 3beta-hydroxysteriod dehydrogenase , pH 7.4, 37°C
0.0082
dicyclohexyl phthalate
Homo sapiens
isoform 17beta-hydroxysteroid dehydrogenase type 3, pH 7.4, 37°C
0.0255
dicyclohexyl phthalate
Homo sapiens
isoform 3beta-hydroxysteriod dehydrogenase, pH 7.4, 37°C
0.0091
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
Homo sapiens
-
IC50: 0.0091 mM, reduction of androstenedione
0.00915
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
Homo sapiens
-
IC50: 0.00915 mM
0.0122
canadine
Homo sapiens
pH 7.4, 37°C, determined with the oracin to dihydrooracin assay
0.029
canadine
Homo sapiens
pH 7.4, 37°C, determined with the reduction of androstenedione to testosterone assay
0.00046
indomethacin
Homo sapiens
pH 7.4, 37°C, determined with the oracin to dihydrooracin assay
0.0037
indomethacin
Homo sapiens
pH 7.4, 37°C, determined with the reduction of androstenedione to testosterone assay
0.0009
Stylopine
Homo sapiens
pH 7.4, 37°C, determined with the oracin to dihydrooracin assay
0.0077
Stylopine
Homo sapiens
pH 7.4, 37°C, determined with the reduction of androstenedione to testosterone assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
the enzyme (17beta-HSD3) is over-expressed in hormone-dependent prostate cancer
uniform, diffuse, and strong expression of isoform AKR1C3 in normal endometrial epithelium but not in endometrial stromal cells. The expression of AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
uniform, diffuse, and strong expression of isoform AKR1C3 in normal endometrial epithelium but not in endometrial stromal cells. The expression of AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
strong isoform AKR1C3 immunoreactivity in columnar epithelium but only weak immunoreactivity in squamous epithelium of the gastrointestinal junction
-
17beta-HSD type 3 (HSD17B3) is expressed almost exclusively in testicular Leydig cells
-
strong isoform AKR1C3 immunoreactivity in bronchial epithelium but not in bronchial glands or alveolar pneumocytes
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
additional information
additional information
-
no isoform AKR1C3 immunoreactivity in bronchial glands or alveolar pneumocytes and small cell carcinoma of the lung, only weak immunoreactivity in squamous epithelium of the gastrointestinal junction
additional information
the enzyme is frequently upregulated in various cancers
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
isoform 17beta-HSD3 shows a cytoplasmic orientation and dependence on glucose-6-phosphate dehydrogenase-generated NADPH
-
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
metabolism
physiological function
isoform 17beta-HSD3-dependent reduction of 4-androstene-3,17-dione is affected by neither coexpression with 11beta-HSD1, EC 1.1.1.146, nor overexpression or knock-down of hexose-6-phosphate dehydrogenase. Knock-down of glucose-6-phosphate dehydrogenase decreases 17beta-HSD3 activity, indicating dependence on cytoplasmic NADPH. Cytoplasmic orientation of isoform 17beta-HSD3 and dependence on glucose-6-phosphate dehydrogenase-generated NADPH explain the lack of a direct functional coupling with the luminal 11beta-HSD1-mediated glucocorticoid metabolism
evolution
the enzyme belongs to the AKR1C subfamily, the members of which catalyze the reduction of ketosteroids and ketoprostaglandins
malfunction
metabolism
-
enzyme 17beta-HSD3 acts in the last step of the biosynthesis of testosterone
physiological function
drug target
since 17beta-HSD3 plays a central role in testosterone production, it is a promising therapeutic target to reduce the circulating level of androgens and to suppress androgen-sensitive tumor proliferation
drug target
the enzyme is a potential therapeutic target for hormone-dependent prostate cancer
metabolism
the enzyme catalyzes the last step in the biosynthesis of the potent androgen testosterone (T), by stereoselectively reducing the C17 ketone of 4-androstene-3,17-dione (4-dione), with NADPH as cofactor
malfunction
-
AKR1C3 knockdown is accomplished in cultured adrenal cells (H295R) using small interfering RNA. Decreasing adrenal cell expression of AKR1C3 mRNA and protein inhibit testosterone production in the H295R adrenal cell line
malfunction
-
mutations of HSD17B3 genes cause a 46,XY disorder of sexual development (46,XY DSD) as a result of low testosterone production
physiological function
exposure of HCT-15 cells to cisplatin results in aquisition of cisplatin resistance and concomitant induction of isoform AKR1C3 and aldo-keto reductase AKR1C1 expression. The resistance lowers the sensitivity toward cellular damages evoked by oxidative stress-derived aldehydes, 4-hydroxy-2-nonenal and 4-oxo-2-nonenal that are detoxified by AKR1C1 and AKR1C3. Overexpression of AKR1C1 or AKR1C3 in the parental HCT15 cells mitigates the cytotoxicity of the aldehydes and cisplatin. Knockdown of both AKR1C1 and AKR1C3 in the resistant cells or treatment of the cells with specific inhibitors of the aldo-keto reductases increases the sensitivity to ciplatin toxicity
physiological function
in LNCaP and LNCaP-AKR1C3 cells overexpressing isoform AKR1C3, metabolism proceeds via 5alpha-reduction to form 5alpha-androstane-3,17-dione and then (epi)androsterone-3-glucuronide. LNCaP-AKR1C3 cells make significantly higher amounts of testosterone-17beta-glucuronide. When 5alpha-reductase is inhibited by finasteride, the production of testosterone-17beta-glucuronide is further elevated in LNCaP-AKR1C3 cells. When AKR1C3 activity is inhibited with indomethacin the production of testosterone-17beta-glucuronide is significantly decreased. 4-Androstene-3,17-dione treatment stimulates cell proliferation in both cell lines. LNCaP-AKR1C3 cells are resistant to the growth inhibitory properties of finasteride, consistent with the diversion of 4-androstene-3,17-dione metabolism from 5alpha-reduced androgens to increased formation of testosterone
physiological function
AKR1C3 is an important human enzyme that participates in the reduction of steroids and prostaglandins, which leads to proliferative signalling. In addition, this enzyme also participates in the biotransformation of xenobiotics, such as drugs and procarcinogens. AKR1C3 is involved in the development of both hormone-dependent and hormone-independent cancers and confers cell resistance to anthracyclines. Role ofAKR1C3in hormone-dependent (e.g., breast, prostate and endometrium) and hormone-independent (e.g., lung, brain, and kidney) cancers
physiological function
-
the enzyme (HSD17B3) contributes to development of male sexual characteristics by converting androstenedione (A4) to testosterone
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). DHB3_HUMAN
310
3
34516
Swiss-Prot
Secretory Pathway (Reliability: 1)
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
10 ns molecular dynamics simulations of inhibitor bound to isofrom AKR1C3. Binding could induce conformational changes to both inhibitor and enzyme. The compound presumably assumes a stable, energetically favored, planar conformation
docking of inhibitors (2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid, (2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid, (2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid and (2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid to crystal structure. Compounds occupy a similar position of the active site as the co-crystallized indomethacin, with the Aryl1 overlapping with the p-chlorobenzoyl moiety of the indomethacin and the Aryl2 overlapping with an indole part of the indomethacin
in complex with 3-phenoxybenzoic acid, to 1.68 A resolution, space group P212121
in complex with inhibitor 1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one. The 2-pyrrolidinone does not interact directly with residues in the oxyanion hole
in complex with inhibitor 3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid. Compound adopts a similar binding orientation as flufenamic acid, however, its phenylamino ring projects deeper into a subpocket and confers selectivity over the other AKR1C isoforms
purified recombinant enzyme in ternary complex with NADP+ and one inhibitor, from inhibitors 1-6, 15 mg/ml protein in 10 mM potassium phosphate pH 7.4, 500 mM NaCl, 1 mM ethylenediaminetetraacetic acid, 1 mM dithiothreitol is mixed with crystallization solution containing 0.1 M sodium citrate, pH 5.5, 0.4 M ammonium acetate, 2.5% v/v 2-methyl-2,4-pentanediol, 22-30% w/v PEG 4000 for inhibitors 1-4, and containing 0.1 M HEPES pH 6.5, 0.2 M ammonium dihydrogen phosphate, 20-25% w/v PEG 3350 for inhibitors 5 and 6, X-ray diffraction structure determination analysis at 1.55-2.81 A resolution, modelling
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
R80I
-
mutant enzyme shows negligible conversion of androst-4-ene-3,17-dione to testosterone. The Km-value for androstenedione is 80fold higher than the KM-value for the wild-type enzyme
R80K
-
conversion of androst-4-ene-3,17-dione to testosterone is reduced as compared to wild-type enzyme. The Km-value for androstenedione is 3.5fold higher than the KM-value for the wild-type enzyme
R80L
-
conversion of androst-4-ene-3,17-dione to testosterone is strongly reduced as compared to wild-type enzyme. The Km-value for androstenedione is 21.6fold higher than the KM-value for the wild-type enzyme
R80M
-
mutant enzyme shows negligible conversion of androst-4-ene-3,17-dione to testosterone. The Km-value for androstenedione is 90.7fold higher than the KM-value for the wild-type enzyme
R80Q
R80Y
-
mutant enzyme shows negligible conversion of androst-4-ene-3,17-dione to testosterone. The Km-value for androstenedione is 85.1fold higher than the KM-value for the wild-type enzyme
R80Q
-
mutant enzyme shows negligible conversion of androst-4-ene-3,17-dione to testosterone. The Km-value for androstenedione is 61.5fold higher than the KM-value for the wild-type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity and anion exchange chromatography, gel fitration, and ultrafiltration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
17beta-hydroxysteroid dehydrogenase 3, expressed in human embryonic kidney 293 cells
-
HEK-293 cells are transduced to express human HSD17B3. The system is also applicable to detect the conversion of 11-ketoandrostenedione to 11-ketotestosterone by HSD17B3
-
recombinant expression of C-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
curcumin analog H10 inhibits the production of 17beta-HSD3 in vitro. It has no effect on the expression levels of 17beta-HSD3, 3betaHSD1, CYP17alpha1, CYP11alpha1, and STAR. H10 could serve as an effective inhibitor of 17beta-HSD3, which in turn would inhibit the biosynthesis of androgens and progression of prostate cancer
in thrombocythemia, a rare myeloproliferative disorder, 17beta-HSD3 is down-regulated about 4.5fold
the enzyme (17beta-HSD3) is over-expressed in hormone-dependent prostate cancer. 17beta-HSD3 mRNA increases over 30fold in cancerous prostate biopsies and the enzyme is overexpressed 8fold in LuCaP-23 and LuCAP-35 cell lines, obtained from metastatic tissues of a patient resistant to castration therapy
exposure of HCT-15 cells to cisplatin results in aquisition of cisplatin resistance and concomitant induction of isoform AKR1C3 and aldo-keto reductase AKR1C1 expression
the expression of isoform AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
diagnostics
-
evaluation of 17beta-HSD3 enzymatic activity using androgen receptor-mediated transactivation is important for understanding and diagnosing the 46,XY disorder of sexual development caused by mutations of HSD17B3 genes which results in low testosterone production. A method is adapted that easily evaluates enzymatic activity of 17beta-HSD3 by quantifying the conversion from androstenedione to trestosterone using androgen receptor-mediated transactivation
drug development
testosterone is converted to 5alpha-dihydrotestosterone, which is present at high concentrations in patients with castration resistant prostate cancer (CRPC). Inhibition of 17beta-HSD5 is therefore considered to be a promising therapy for treating CRPC. High-throughput inhibitor screening, overview
medicine
medicine
exposure of HCT-15 cells to cisplatin results in aquisition of cisplatin resistance and concomitant induction of isoform AKR1C3 and aldo-keto reductase AKR1C1 expression. The resistance lowers the sensitivity toward cellular damages evoked by oxidative stress-derived aldehydes, 4-hydroxy-2-nonenal and 4-oxo-2-nonenal that are detoxified by AKR1C1 and AKR1C3. Overexpression of AKR1C1 or AKR1C3 in the parental HCT15 cells mitigates the cytotoxicity of the aldehydes and cisplatin. Knockdown of both AKR1C1 and AKR1C3 in the resistant cells or treatment of the cells with specific inhibitors of the aldo-keto reductases increases the sensitivity to ciplatin toxicity. Pretreatment of the resistant cells with proteasome inhibitor Z-Leu-Leu-Leu-al augments the cisplatin sensitization elicited by aldo-keto reductase inhibitors
medicine
-
positive isoform AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction. Isoform AKR1C3 immunoreactivity is absent in small cell carcinoma of the lung
medicine
uniform, diffuse, and strong expression of isoform AKR1C3 in normal endometrial epithelium but not in endometrial stromal cells. The expression of AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Andersson, S.; Geissler, W.M.; Wu, L.; Davis, D.L.; Grumbach, M.M.; New, M.I.; Schwarz, H.P.; Blethen, S.L.; Mendoca.B.B.; Bloise, W.; Witchel, S.F.; Cutler, G.B.; Griffin, J.E.; Wilson, J.D.; Russell, D.W.
Molecular genetics and pathophysiology of 17beta-hydroxysteroid dehydrogenase 3 deficiency
J. Clin. Endocrinol.
81
130-136
1996
Homo sapiens
Baker, M.E.
Unusual evolution of 11beta- and 17beta-hydroxysteroid dehydrogenases
BioEssays
18
63-70
1995
Homo sapiens
Geissler, W.M.; Davis, D.L.; Wu, L.; Bradshaw, K.D.; Patel, S.; Mendoca, B.B.; Elliston, K.O.; Wilson, J.D.; Russell, D.W.; Andersson, S.
Male pseudohermaphroditism caused by mutations of testicular 17beta-hydroxysteroid dehydrogenase 3
Nature Genet.
7
34-39
1994
Homo sapiens
Oshima, H.; Ochiai, K.
On testicular 17beta-hydroxysteroid oxidoreductase product activation of testosterone formation from androstendione in vitro
Biochim. Biophys. Acta
306
227-236
1973
Oryctolagus cuniculus, Homo sapiens
Khan, N.; Sharma, K.K.; Andersson, S.; Auchus, R.J.
Human 17beta-hydroxysteroid dehydrogenases types 1, 2, and 3 catalyze bi-directional equilibrium reactions, rather than unidirectional metabolism, in HEK-293 cells
Arch. Biochem. Biophys.
429
50-59
2004
Homo sapiens
McKeever, B.M.; Hawkins, B.K.; Geissler, W.M.; Wu, L.; Sheridan, R.P.; Mosley, R.T.; Andersson, S.
Amino acid substitution of arginine 80 in 17beta-hydroxysteroid dehydrogenase type 3 and its effect on NADPH cofactor binding and oxidation/reduction kinetics
Biochim. Biophys. Acta
1601
29-37
2002
Homo sapiens
Poirier, D.
Inhibitors of 17beta-hydroxysteroid dehydrogenases
Curr. Med. Chem.
10
453-477
2003
Canis lupus familiaris, Homo sapiens, Rattus norvegicus
le Lain, R.; Barrell, K.J.; Saeed, G.S.; Nicholls, P.J.; Simons, C.; Kirby, A.; Smith, H.J.
Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme
J. Enzyme Inhib. Med. Chem.
17
93-100
2002
Homo sapiens
Tchedam Ngatcha, B.; Luu-The, V.; Labrie, F.; Poirier, D.
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship
J. Med. Chem.
48
5257-5268
2005
Homo sapiens
Mindnich, R.; Haller, F.; Halbach, F.; Moeller, G.; Hrabe de Angelis, M.; Adamski, J.
Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme
J. Mol. Endocrinol.
35
305-316
2005
Danio rerio, Homo sapiens
Brozic, P.; Golob, B.; Gomboc, N.; Rizner, T.L.; Gobec, S.
Cinnamic acids as new inhibitors of 17beta-hydroxysteroid dehydrogenase type 5 (AKR1C3)
Mol. Cell. Endocrinol.
248
233-235
2006
Homo sapiens
Moeller, G.; Adamski, J.
Multifunctionality of human 17beta-hydroxysteroid dehydrogenases
Mol. Cell. Endocrinol.
248
47-55
2006
Homo sapiens
Hu, G.X.; Zhou, H.Y.; Li, X.W.; Chen, B.B.; Xiao, Y.C.; Lian, Q.Q.; Liang, G.; Kim, H.H.; Zheng, Z.Q.; Hardy, D.O.; Ge, R.S.
The (+)- and (-)-gossypols potently inhibit both 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 in human and rat testes
J. Steroid Biochem. Mol. Biol.
115
14-19
2009
Homo sapiens, Rattus norvegicus
Day, J.M.; Tutill, H.J.; Foster, P.A.; Bailey, H.V.; Heaton, W.B.; Sharland, C.M.; Vicker, N.; Potter, B.V.; Purohit, A.; Reed, M.J.
Development of hormone-dependent prostate cancer models for the evaluation of inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Mol. Cell. Endocrinol.
301
251-258
2009
Homo sapiens
Nakamura, Y.; Hornsby, P.; Casson, P.; Morimoto, R.; Satoh, F.; Xing, Y.; Kennedy, M.; Sasano, H.; Rainey, W.
Type 5 17-hydroxysteroid dehydrogenase (AKR1C3) contributes to testosterone production in the adrenal reticularis
J. Clin. Endocrinol. Metab.
94
2192-2198
2009
Homo sapiens
Jackson, V.J.; Yosaatmadja, Y.; Flanagan, J.U.; Squire, C.J.
Structure of AKR1C3 with 3-phenoxybenzoic acid bound
Acta Crystallogr. Sect. F
68
409-413
2012
Homo sapiens (P42330)
Adeniji, A.O.; Twenter, B.M.; Byrns, M.C.; Jin, Y.; Winkler, J.D.; Penning, T.M.
Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3)
Bioorg. Med. Chem. Lett.
21
1464-1468
2011
Homo sapiens (P42330)
Chen, M.; Adeniji, A.O.; Twenter, B.M.; Winkler, J.D.; Christianson, D.W.; Penning, T.M.
Crystal structures of AKR1C3 containing an N-(aryl)amino-benzoate inhibitor and a bifunctional AKR1C3 inhibitor and androgen receptor antagonist. Therapeutic leads for castrate resistant prostate cancer
Bioorg. Med. Chem. Lett.
22
3492-3497
2012
Homo sapiens (P42330)
Harada, K.; Kubo, H.; Tanaka, A.; Nishioka, K.
Identification of oxazolidinediones and thiazolidinediones as potent 17beta-hydroxysteroid dehydrogenase type 3 inhibitors
Bioorg. Med. Chem. Lett.
22
504-507
2012
Homo sapiens (P37058)
Sinreih, M.; Sosic, I.; Beranic, N.; Turk, S.; Adeniji, A.O.; Penning, T.M.; Rizner, T.L.; Gobec, S.
N-Benzoyl anthranilic acid derivatives as selective inhibitors of aldo-keto reductase AKR1C3
Bioorg. Med. Chem. Lett.
22
5948-5951
2012
Homo sapiens (P42330)
Maltais, R.; Fournier, M.A.; Poirier, D.
Development of 3-substituted-androsterone derivatives as potent inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem.
19
4652-4668
2011
Homo sapiens (P37058)
Harada, K.; Kubo, H.; Abe, J.; Haneta, M.; Conception, A.; Inoue, S.; Okada, S.; Nishioka, K.
Discovery of potent and orally bioavailable 17beta-hydroxysteroid dehydrogenase type 3 inhibitors
Bioorg. Med. Chem.
20
3242-3254
2012
Rattus norvegicus, Homo sapiens (P37058)
Yuan, K.; Zhao, B.; Li, X.W.; Hu, G.X.; Su, Y.; Chu, Y.; Akingbemi, B.T.; Lian, Q.Q.; Ge, R.S.
Effects of phthalates on 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities in human and rat testes
Chem. Biol. Interact.
195
180-188
2012
Rattus norvegicus, Homo sapiens (P37058)
Matsunaga, T.; Hojo, A.; Yamane, Y.; Endo, S.; El-Kabbani, O.; Hara, A.
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers
Chem. Biol. Interact.
202
234-242
2013
Homo sapiens (P42330)
Legeza, B.; Balazs, Z.; Nashev, L.G.; Odermatt, A.
The microsomal enzyme 17beta-hydroxysteroid dehydrogenase 3 faces the cytoplasm and uses NADPH generated by glucose-6-phosphate dehydrogenase
Endocrinology
154
205-213
2013
Homo sapiens (P37058)
Heinrich, D.M.; Flanagan, J.U.; Jamieson, S.M.; Silva, S.; Rigoreau, L.J.; Trivier, E.; Raynham, T.; Turnbull, A.P.; Denny, W.A.
Synthesis and structure-activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
Eur. J. Med. Chem.
62
738-744
2013
Homo sapiens (P42330)
Gazvoda, M.; Beranic, N.; Turk, S.; Burja, B.; Kocevar, M.; Rizner, T.L.; Gobec, S.; Polanc, S.
2,3-diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17?-hydroxysteroid dehydrogenase (AKR1C3)
Eur. J. Med. Chem.
62
89-97
2013
Homo sapiens (P42330)
Zakharov, V.; Lin, H.K.; Azzarello, J.; McMeekin, S.; Moore, K.N.; Penning, T.M.; Fung, K.M.
Suppressed expression of type 2 3alpha/type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3) in endometrial hyperplasia and carcinoma
Int. J. Clin. Exp. Pathol.
3
608-617
2010
Homo sapiens (P42330)
Miller, V.L.; Lin, H.K.; Murugan, P.; Fan, M.; Penning, T.M.; Brame, L.S.; Yang, Q.; Fung, K.M.
Aldo-keto reductase family 1 member C3 (AKR1C3) is expressed in adenocarcinoma and squamous cell carcinoma but not small cell carcinoma
Int. J. Clin. Exp. Pathol.
5
278-289
2012
Homo sapiens
Brozic, P.; Turk, S.; Adeniji, A.O.; Konc, J.; Janezic, D.; Penning, T.M.; Lanisnik Rizner, T.; Gobec, S.
Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library
J. Med. Chem.
55
7417-7424
2012
Homo sapiens (P42330)
Byrns, M.C.; Mindnich, R.; Duan, L.; Penning, T.M.
Overexpression of aldo-keto reductase 1C3 (AKR1C3) in LNCaP cells diverts androgen metabolism towards testosterone resulting in resistance to the 5alpha-reductase inhibitor finasteride
J. Steroid Biochem. Mol. Biol.
130
7-15
2012
Homo sapiens (P42330)
Amano, Y.; Yamaguchi, T.; Niimi, T.; Sakashita, H.
Structures of complexes of type 5 17beta-hydroxysteroid dehydrogenase with structurally diverse inhibitors: insights into the conformational changes upon inhibitor binding
Acta Crystallogr. Sect. D
71
918-927
2015
Homo sapiens (P42330)
Djigoue, G.B.; Kenmogne, L.C.; Roy, J.; Maltais, R.; Poirier, D.
Design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem.
23
5433-5451
2015
Homo sapiens
Skarydova, L.; Hofman, J.; Chlebek, J.; Havrankova, J.; Kosanova, K.; Skarka, A.; Hostalkova, A.; Plucha, T.; Cahlikova, L.; Wsol, V.
Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors
J. Steroid Biochem. Mol. Biol.
143
250-258
2014
Homo sapiens (P42330)
Roy, J.; Fournier, M.A.; Maltais, R.; Kenmogne, L.C.; Poirier, D.
Reprint of in vitro and in vivo evaluation of a 3beta-androsterone derivative as inhibitor of 17beta-hydroxysteroid dehydrogenase type 3
J. Steroid Biochem. Mol. Biol.
153
170-178
2015
Homo sapiens (P37058), Rattus norvegicus (O54939), Rattus norvegicus Sprague-Dawley (O54939)
Cheng, Y.; Yang, Y.; Wu, Y.; Wang, W.; Xiao, L.; Zhang, Y.; Tang, J.; Huang, Y.D.; Zhang, S.; Xiang, Q.
The curcumin derivative, H10, suppresses hormone-dependent prostate cancer by inhibiting 17beta-hydroxysteroid dehydrogenase type 3
Front. Pharmacol.
11
637
2020
Homo sapiens (P37058)
Yazawa, T.; Imamichi, Y.; Uwada, J.; Sekiguchi, T.; Mikami, D.; Kitano, T.; Ida, T.; Sato, T.; Nemoto, T.; Nagata, S.; Islam Khan, M.R.; Takahashi, S.; Ushikubi, F.; Suzuki, N.; Umezawa, A.; Taniguchi, T.
Evaluation of 17beta-hydroxysteroid dehydrogenase activity using androgen receptor-mediated transactivation
J. Steroid Biochem. Mol. Biol.
196
105493
2020
Homo sapiens
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