1.1.1.64: testosterone 17beta-dehydrogenase (NADP+)

This is an abbreviated version, for detailed information about testosterone 17beta-dehydrogenase (NADP+), go to the full flat file.

Reaction

testosterone
+
NADP+
=
androstenedione
+
NADPH
+
H+

Synonyms

17-ketoreductase, 17beta-HSD, 17beta-HSD 3, 17beta-HSD type 3, 17beta-HSD type 5, 17beta-HSD-3, 17beta-HSD1, 17beta-HSD3, 17beta-HSD4, 17beta-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase 3, 17beta-hydroxysteroid dehydrogenase type 3, 17beta-hydroxysteroid dehydrogenase type 5, 17beta-hydroxysteroid dehydrogenases type 3, 17betaHSD3, 3beta-hydroxysteroid dehydrogenase type 3, AKR1C3, More, NADP-dependent testosterone-17beta-oxidoreductase, type 3 17beta-HSD, type 3 17beta-hydroxysteroid dehydrogenase, type 5 beta-hydroxysteroid dehydrogenase

ECTree

     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+)

Inhibitors

Inhibitors on EC 1.1.1.64 - testosterone 17beta-dehydrogenase (NADP+)

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-gossypol
(-)-gossypol
(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
(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,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
(RS)-3(2,3,3-triphenyl-prop-2-enoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
(RS)-3(3'-phenylpropoxycarbonyl)-3(prop-2-ynyl)pyrrolidine-2,5-dione
-
IC50: 0.0421 mM
1-(4-hydroxyphenyl)-butan-1-one
-
IC50: 0.08951 mM
1-(4-hydroxyphenyl)-ethanone
-
IC50: 1.70892 mM
1-(4-hydroxyphenyl)-heptan-1-one
-
IC50: 0.0784 mM
1-(4-hydroxyphenyl)-hexan-1-one
-
IC50: 0.01802 mM
1-(4-hydroxyphenyl)-nonan-1-one
-
IC50: 0.00286 mM
1-(4-hydroxyphenyl)-octan-1-one
-
IC50: 0.00652 mM
1-(4-hydroxyphenyl)-pentan-1-one
-
IC50: 0.00497 mM; IC50: 0.06052 mM
1-(4-hydroxyphenyl)-propan-1-one
-
IC50: 0.15056 mM
1-(4-hydroxyphenyl)-undeca-1-one
-
IC50: 0.00755 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-[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
2,5-diphenyl-p-benzoquinone
-
IC50: 0.0027 mM, reduction of androstenedione
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
2-methylcinnamic acid
-
IC50: 0.0064 mM
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
-
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
-
-
3,4,5-trimethoxycinnamic acid
-
IC50: 0.049 mM
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-coumaric acid
-
34% inhibition at 0.05 mM
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-cyclohexylpropanoic acid
-
weak inhibition, IC50: 0.1 mM, above
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-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-trifluoromethylcinnamic acid
-
IC50: 0.043 mM
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
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
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-(2'-hydroxypropanoxy)-5alpha-androstan-17-one
-
0.003 mM, 89% inhibition
3alpha-(3'-bromopropanoxy)-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3alpha-(3'-hydroxypropanoxy)-5alpha-androstan-17-one
-
0.003 mM, 86% inhibition
3alpha-(prop-2'-enoxy)-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition
3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 92% inhibition, IC50: 352 nM
3alpha-ethoxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition
3alpha-hexanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
-
0.003 mM, 28% inhibition
3alpha-hexanoxy-5alpha-androstan-17-one
-
0.003 mM, 92% 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-methyl-5alpha-androstan-17-one
-
0.003 mM, 93% 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-hydroxy-3beta-vinyl-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
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-methoxy-5alpha-androstan-17-one
-
0.003 mM, 94% inhibition
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
3alpha-propanoxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition
3b-Methyl-5a-androstan-3a-ol-17-on
-
-
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-cyclohexylethyl-androsterone
-
IC50: 60 nM
3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 95% inhibition, IC50: 87 nM
3beta-dodecyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 77% inhibition
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-methyl-5alpha-androstan-17-one
-
0.003 mM, 16% inhibition
3beta-hydroxy-3alpha-phenyl-5alpha-androstan-17-one
-
0.003 mM, 39% inhibition
3beta-hydroxy-3alpha-phenylmethyl-5alpha-androstan-17-one
-
0.003 mM, 39% inhibition
3beta-hydroxy-3alpha-propyl-5alpha-androstan-17-one
-
0.003 mM, 33% 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-phenylmethyl-androsterone
-
IC50: 57 nM
3beta-propyl-androsterone
-
IC50: 67 nM
3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 90% inhibition, IC50: 73 nM
3beta-sec-butyl-androsterone
-
IC50: 73 nM
3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
-
0.003 mM, 93% inhibition, IC50: 142 nM
4-estrene-3,17-dione
-
-
4-Methylumbelliferone
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-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-androstene-3,17-dione
-
-
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-[3,5-dichloro-4-(phosphonoxy)benzylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
7-hydroxyflavone
atamestane
-
-
baicalein
Biochanin A
-
IC50: 0.0108 mM, reduction of androstenedione
bis(2-butoxyethyl) phthalate
caffeic acid
-
18% inhibition at 0.05 mM
Cinnamic acid
-
IC50: 0.050 mM
clomiphene
-
IC50: 0.0762 mM
coumarin-3-carboxylic acid
-
30% inhibition at 0.05 mM
CuCl2
-
10 mM, 40% inhibition
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
dicyclohexyl phthalate
FeCl3
-
10 mM, 54% inhibition
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
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
p-chloromercuribenzoate
-
10 mM, strong inhibition, 5% residual activity is reversed to 65% activity by either 1 mM glutathione or cysteine
Pb(NO3)2
-
10 mM, 30% inhibition
phenyl-p-benzoquinone
-
IC50: 0.0057 mM, reduction of androstenedione
S-petasin
-
-
Sodium amytal
-
10 mM, 25% inhibition
Sodium cyanide
-
10 mM, progressive and marked inhibition
STX-2171
-
-
STX-2622
-
-
STX-2624
-
-
tamoxifen
-
IC50: 0.098 mM, time-dependent and irreversible
testosterone
-
1 mM, 62.8% inhibition of androstendione reduction
umbelliferone
ZnCl2
-
10 mM, 90% inhibition
additional information
-
activity of 17beta-HSD is significantly decreased in metyrapone-induced corticosterone-deficient rat Leydig cells compared to control, whereas simultaneous administration of corticosterone partially prevented this and maintained the activity at near normal levels
-