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Information on EC 1.1.1.64 - testosterone 17beta-dehydrogenase (NADP+)
for references in articles please use BRENDA:EC1.1.1.64
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.64 testosterone 17beta-dehydrogenase (NADP+)
IUBMB Comments
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 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
showSynonyms
17betahsd3, 17beta-hydroxysteroid dehydrogenase 3, 17beta-hsd 3, testosterone 17beta-dehydrogenase (nadp+), more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17-ketoreductase
-
-
-
-
17beta-HSD 3
17beta-HSD3
17beta-hydroxysteroid dehydrogenase
17beta-hydroxysteroid dehydrogenase 3
17beta-hydroxysteroid dehydrogenase type 3
AKR1C3
HSD17B3
NADP-dependent testosterone-17beta-oxidoreductase
-
-
-
-
type 3 17beta-HSD
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NADP+ = androstenedione + NADPH + H+
4-pro-S-hydrogen atom of NADPH is transferred to the alpha-face of the steroid molecule
-
testosterone + NADP+ = androstenedione + NADPH + H+
4-pro-R-hydrogen atom of NADPH is transferred to the alpha-face of the steroid molecule
-
testosterone + NADP+ = androstenedione + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
11-oxyandrogens biosynthesis, androgen biosynthesis, backdoor pathway of androgen biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
17beta-hydroxysteroid:NADP+ 17-oxidoreductase
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
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CAS REGISTRY NUMBER
COMMENTARY
9028-63-1
-
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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
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
Substrates: -
Products: -
Products: -
?
1,2,3,4-tetrahydro-1-naphthol + NADP+
1,2,3,4-tetrahydro-1-naphthone + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
1-acenaphthenol + NADP+
1-acenaphthenone + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
19-nortestosterone + NADP+
19-norandrostenedione + NADPH
-
Substrates: 93% activity compared to testosterone oxidation
Products: -
Products: -
r
4-oxo-2-nonenal + NADPH + H+
4-hydroxy-2-nonenal + NADP+
Substrates: -
Products: -
Products: -
?
5alpha-androstane-17beta-ol-3-one + NADP+
5alpha-androstane-3,17-dione + NADPH
-
Substrates: 30% activity compared to testosterone oxidation
Products: -
Products: -
r
5alpha-dihydrotestosterone + NADP+
5alpha-17-oxo-dihydrotestosterone + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
5beta-androstane-17beta-ol + NADP+
5alpha-androstane-17-one + NADPH
-
Substrates: 117% activity compared to testosterone oxidation
Products: -
Products: -
r
5beta-androstane-17beta-ol-3-one + NADP+
5beta-androstane-3,17-dione + NADPH
-
Substrates: 330% activity compared to testosterone oxidation
Products: -
Products: -
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
5beta-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
-
Substrates: -
Products: -
Products: -
r
androst-4-ene-3,17-dione + NADPH + H+
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androstanedione + NADPH
dihydrotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androsterone + NADPH + H+
androstane-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
?
benzene dihydrodiol + NADP+
o-benzoquinone + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
cyclohex-2-en-1-ol + NADP+
cyclohex-2-en-1-one + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
dehydroepiandrosterone + NADPH
androst-5-ene-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
r
indan-1-ol + NADP+
indan-1-one + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
pyridine-4-aldehyde + NADPH
pyridine-4-alcohol + NADP+
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
11-hydroxy-androstenedione + NADPH
11beta-hydroxy-testosterone
-
Substrates: -
Products: -
Products: -
?
11-hydroxy-androstenedione + NADPH
11beta-hydroxy-testosterone
-
Substrates: -
Products: -
Products: -
?
11-ketoandrostenedione + NADPH
11-ketotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
11-ketoandrostenedione + NADPH
11-ketotestosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
-
Substrates: 93% activity compared to testosterone oxidation
Products: -
Products: -
r
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
-
Substrates: 63% activity compared to testosterone oxidation
Products: -
Products: -
r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
-
Substrates: 25% activity compared to testosterone oxidation
Products: -
Products: -
r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
-
Substrates: 134% activity compared to testosterone oxidation
Products: -
Products: -
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
-
Substrates: 1180% activity compared to testosterone oxidation
Products: -
Products: -
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
5beta-dihydrotestosterone + NADP+
5beta-17-oxo-dihydrotestosterone + NADPH
-
Substrates: -
Products: -
Products: -
?
5beta-dihydrotestosterone + NADP+
5beta-17-oxo-dihydrotestosterone + NADPH
-
Substrates: isoenzymes 1 and 2
Products: -
Products: -
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
Substrates: 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
Products: -
Products: -
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
Substrates: convertion of the weak androgen androstendione into the potent androgen testosterone
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: the equilibrium state is 92% testosterone to 8% androstenedione
Products: -
Products: -
r
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: the enzyme is involved in biosynthesis of testosterone
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: 17beta-HSD3
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: -
Products: i.e. 4-androsten-17-ol-3-one
Products: i.e. 4-androsten-17-ol-3-one
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: 17beta-HSD3
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1.146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
Products: i.e. 4-androsten-17beta-ol-3-one
Products: i.e. 4-androsten-17beta-ol-3-one
?
dehydroepiandrosterone + NADPH
androst-5-en-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
?
dehydroepiandrosterone + NADPH
androst-5-en-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
?
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
?
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
-
Substrates: -
Products: -
Products: -
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
Substrates: -
Products: -
Products: -
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
Substrates: NADP+ is preferred
Products: -
Products: -
r
testosterone + NAD+
androstenedione + NADH
-
Substrates: NAD+ shows ess than 10% of the activity with NADP+
Products: -
Products: -
ir
testosterone + NAD+
androstenedione + NADH
-
Substrates: NAD+ shows 20% of the activity with NADP+
Products: -
Products: -
ir
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: 17beta-hydroxysteroid dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: 17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: rate of oxidation is less than 30% of those for reduction
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
?
testosterone + NADP+
androstenedione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
?
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
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
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
Substrates: NADP+ is preferred
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
17beta-estradiol + NADP+
estrone + NADPH
-
Substrates: -
Products: -
Products: -
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
Substrates: 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
Products: -
Products: -
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
-
Substrates: convertion of the weak androgen androstendione into the potent androgen testosterone
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: the enzyme is involved in biosynthesis of testosterone
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
-
Substrates: -
Products: -
Products: -
?
androstenedione + NADPH + H+
testosterone + NADP+
Substrates: the two reactions 11beta-HSD1-dehydrogenase, EC 1.1.1.146, and 17beta-HSD3, EC 1.1.1.64, which utilize NADPH are competing for NADPH from the same cofactor pool. 11beta-HSD1-dehydrogenase serves as a NADPH-regenerating system that is tightly coupled in regulating 17beta-HSD3 reaction synthesizing testosterone. A cycle can exist whereby the NADPH produced by 11beta-HSD1 dehydrogenase can drive the reductase activity of 17beta-HSD3 and the NADP+ produced by 17beta-HSD3 and other enzymes involved in testosterone biosynthesis can drive the dehydrogenase activity of 11beta-HSD1
Products: i.e. 4-androsten-17beta-ol-3-one
Products: i.e. 4-androsten-17beta-ol-3-one
?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: 17beta-hydroxysterod dehydrogenase 3, reduction of androst-4-ene-3,17-dione is preferred
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
?
testosterone + NADP+
androstenedione + NADPH + H+
-
Substrates: -
Products: -
Products: -
r
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
?
testosterone + NADP+
androstenedione + NADPH + H+
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
isoenzyme 1, 40% of its NADP+ dependent activity, isoenzyme 2, less than 5% of its NADP+ dependent activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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
(3alpha,5alpha)-3-[(2,5-dimethyl-4-{[2-(trifluoromethyl)phenyl]sulfonyl}piperazin-1-yl)methyl]-3-hydroxyandrostan-17-one
the inhibitor RM-532-105 seems to have difficulties in penetrating inside the testis and is concentrated in the testicular capsule. Therefore it is unable to inhibit the 17bets-HSD3 located inside the testis. At a higher concentration, RM-532-105 significantly decreases the level of testosterone and dihydrotestosterone in rat plasma, in vivo effects of the inhibitor in testis and plasma, detailed overview
(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,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,5'R,10S,13S)-4',5'-dibenzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
6.2-19.5% inhibition at 0.0001-0.001 mM
(3R,5'R,10S,13S)-5'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
58.2-90.4% inhibition at 0.0001-0.001 mM
(3R,5'S,10S,13S)-4',5'-dibenzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
25.6-87.3% inhibition at 0.0001-0.001 mM
(3R,5'S,10S,13S)-5'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
18.5-63.2% inhibition at 0.0001-0.001 mM
(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
-
-
(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
(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
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(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
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(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
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(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
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(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
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(3S)-3-benzyl-4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-1-oxa-4-azaspiro[5.5]undecan-2-one
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(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
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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