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

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The expected taxonomic range for this enzyme is: Euteleostomi

EC NUMBER
COMMENTARY hide
1.1.1.64
-
RECOMMENDED NAME
GeneOntology No.
testosterone 17beta-dehydrogenase (NADP+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
testosterone + NADP+ = androstenedione + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen and estrogen metabolism
-
-
androgen biosynthesis
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-
Metabolic pathways
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Steroid hormone biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
17beta-hydroxysteroid:NADP+ 17-oxidoreductase
Also oxidizes 3-hydroxyhexobarbital to 3-oxohexobarbital.
CAS REGISTRY NUMBER
COMMENTARY hide
9028-63-1
-
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+ [View the structure]
show the reaction diagram
-
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
1,2,3,4-tetrahydro-1-naphthol + NADP+
1,2,3,4-tetrahydro-1-naphthone + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
1-acenaphthenol + NADP+
1-acenaphthenone + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
11-hydroxy-androstenedione + NADPH
11beta-hydroxy-testosterone
show the reaction diagram
11-ketoandrostenedione + NADPH
11-ketotestosterone + NADP+
show the reaction diagram
17beta-estradiol + NADP+
estrone + NADPH
show the reaction diagram
19-nortestosterone + NADP+
19-norandrostenedione + NADPH
show the reaction diagram
-
93% activity compared to testosterone oxidation
-
r
4-oxo-2-nonenal + NADPH + H+
4-hydroxy-2-nonenal + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NADP+
5alpha-androstane-3,17-dione + NADPH
show the reaction diagram
-
30% activity compared to testosterone oxidation
-
r
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
show the reaction diagram
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-3beta-ol-17-one + NADPH
show the reaction diagram
5alpha-dihydrotestosterone + NADP+
5alpha-17-oxo-dihydrotestosterone + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
5beta-androstane-17beta-ol + NADP+
5alpha-androstane-17-one + NADPH
show the reaction diagram
-
117% activity compared to testosterone oxidation
-
r
5beta-androstane-17beta-ol-3-one + NADP+
5beta-androstane-3,17-dione + NADPH
show the reaction diagram
-
330% activity compared to testosterone oxidation
-
r
5beta-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-3alpha-ol-17-one + NADPH
show the reaction diagram
-
1180% activity compared to testosterone oxidation
-
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-17-one + NADPH
show the reaction diagram
-
-
-
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH
show the reaction diagram
-
-
-
r
5beta-dihydrotestosterone + NADP+
5beta-17-oxo-dihydrotestosterone + NADPH
show the reaction diagram
9,10-phenanthrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
androst-4-ene-3,17-dione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstanedione + NADPH
dihydrotestosterone + NADP+
show the reaction diagram
-
-
-
-
?
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
androsterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
benzene dihydrodiol + NADP+
o-benzoquinone + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
cyclohex-2-en-1-ol + NADP+
cyclohex-2-en-1-one + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
dehydroepiandrosterone + NADPH
androst-5-en-3beta,17beta-diol + NADP+
show the reaction diagram
dehydroepiandrosterone + NADPH
androst-5-ene-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
r
epiandrosterone + NADPH
androstane-3beta,17beta-diol + NADP+
show the reaction diagram
indan-1-ol + NADP+
indan-1-one + NADPH
show the reaction diagram
-
isoenzymes 1 and 2
-
r
pyridine-4-aldehyde + NADPH
pyridine-4-alcohol + NADP+
show the reaction diagram
-
isoenzymes 1 and 2
-
r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
testosterone + NAD+
androstenedione + NADH
show the reaction diagram
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
show the reaction diagram
additional information
?
-
-
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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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17beta-estradiol + NADP+
estrone + NADPH
show the reaction diagram
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-3alpha-ol-17-one + NADPH
show the reaction diagram
-
-
-
r
androst-4-ene-3,17-dione + NADPH
testosterone + NADP+
show the reaction diagram
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
-
NADP+ is preferred
-
r
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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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
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
testosterone
-
0.023 mM, 2.6fold increase in androstenedione reduction
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.077
17beta-hydroxy-5alpha-androstane-3-one
-
-
0.0067
17beta-hydroxy-5beta-androstane-3-one
-
-
0.053
19-nortestosterone
-
-
0.0031
4-oxo-2-nonenal
-
pH 7.4, 25C
0.023
5alpha-androstane-3alpha,17beta-diol
-
-
0.011
5beta-androstane-3alpha,17beta-diol
-
-
0.029
5beta-androstane-3beta,17beta-diol
-
-
0.0007 - 0.04
androstenedione
0.47 - 6.7
benzene dihydrodiol
0.0033
estrone
-
-
0.1012
NAD+
-
-
0.177
NADH
-
-
0.0046 - 0.047
NADP+
0.0083 - 0.011
NADPH
0.0015 - 0.27
testosterone
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.148
4-oxo-2-nonenal
Homo sapiens
-
pH 7.4, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
47.8
4-oxo-2-nonenal
Homo sapiens
-
pH 7.4, 25C
10426
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
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
0.0024
4-estrene-3,17-dione
-
-
0.0068
5-androstene-3,17-dione
-
-
0.017 - 0.05
bis(2-butoxyethyl) phthalate
0.0055 - 0.0219
dicyclohexyl phthalate
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00113 - 0.01093
(+)-gossypol
0.00036 - 0.00343
(-)-gossypol
0.0136
(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
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
0.000006
(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
0.00008
(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
0.0091 - 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
0.08951
1-(4-hydroxyphenyl)-butan-1-one
Rattus norvegicus
-
IC50: 0.08951 mM
1.70892
1-(4-hydroxyphenyl)-ethanone
Rattus norvegicus
-
IC50: 1.70892 mM
0.0784
1-(4-hydroxyphenyl)-heptan-1-one
Rattus norvegicus
-
IC50: 0.0784 mM
0.01802
1-(4-hydroxyphenyl)-hexan-1-one
Rattus norvegicus
-
IC50: 0.01802 mM
0.00286
1-(4-hydroxyphenyl)-nonan-1-one
Rattus norvegicus
-
IC50: 0.00286 mM
0.00652
1-(4-hydroxyphenyl)-octan-1-one
Rattus norvegicus
-
IC50: 0.00652 mM
0.00497 - 0.06052
1-(4-hydroxyphenyl)-pentan-1-one
0.15056
1-(4-hydroxyphenyl)-propan-1-one
Rattus norvegicus
-
IC50: 0.15056 mM
0.00755
1-(4-hydroxyphenyl)-undeca-1-one
Rattus norvegicus
-
IC50: 0.00755 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
0.0064
2-methylcinnamic acid
Homo sapiens
-
IC50: 0.0064 mM
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
0.049
3,4,5-trimethoxycinnamic acid
Homo sapiens
-
IC50: 0.049 mM
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
0.1
3-cyclohexylpropanoic acid
Homo sapiens
-
weak inhibition, IC50: 0.1 mM, above
0.043
3-trifluoromethylcinnamic acid
Homo sapiens
-
IC50: 0.043 mM
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
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
0.000057
3beta-phenylmethyl-androsterone
Homo sapiens
-
IC50: 57 nM
0.000067
3beta-propyl-androsterone
Homo sapiens
-
IC50: 67 nM
0.000073
3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
0.000142
3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
Homo sapiens
-
0.003 mM, 93% inhibition, IC50: 142 nM
0.0009 - 0.0019
4-Methylumbelliferone
0.000002
5-(3-bromo-4-hydroxybenzylidene)-3-(4-fluorophenyl)-2-thioxo-1,3-oxazolidin-4-one
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
0.000001
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
0.009 - 0.06698
7-hydroxyflavone
0.0093 - 0.18592
baicalein
0.0108
Biochanin A
Homo sapiens
-
IC50: 0.0108 mM, reduction of androstenedione
0.0233 - 0.0825
bis(2-butoxyethyl) phthalate
0.05
Cinnamic acid
Homo sapiens
-
IC50: 0.050 mM
0.0762
clomiphene
Homo sapiens
-
IC50: 0.0762 mM
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
0.0082 - 0.09
dicyclohexyl phthalate
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
0.0057
phenyl-p-benzoquinone
Homo sapiens
-
IC50: 0.0057 mM, reduction of androstenedione
0.000383
STX-2171
Homo sapiens
-
at 37C
0.000201
STX-2622
Homo sapiens
-
at 37C
0.000441
STX-2624
Homo sapiens
-
at 37C
0.098
tamoxifen
Homo sapiens
-
IC50: 0.098 mM, time-dependent and irreversible
0.0014
umbelliferone
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0033
-
enzyme activity in smooth-surfaced microsomes
0.647
-
newly discovered isoenzyme
2.316
-
classical enzymes
96.5
-
enzyme activity in microsomal fraction after centrifugation
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8
-
addition of testosterone shifts optimal pH to 7.4-7.8
6.1
-
reduction of androst-4-ene-3,17-dione
6.5
-
assay at
6.5 - 7.5
-
at 37C
8.5
-
at 50C
10
-
sharp drop of activity above
10.2
-
oxidation of benzene dihydrodiol, isoenzyme 2
10.6
-
oxidation of testosterone
10.8
-
oxidation of benzene dihydrodiol, isoenzyme 1
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 9
-
-
8.5 - 10.5
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
sharp drop of activity above
47
-
classical enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
predominantly expressed in the zona reticularis
Manually annotated by BRENDA team
-
low activity in both sexes
Manually annotated by BRENDA team
-
during embryogenesis the enzyme is present from the sphere stage until hatching
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
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
Manually annotated by BRENDA team
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
Manually annotated by BRENDA team
-
strong isoform AKR1C3 immunoreactivity in columnar epithelium but only weak immunoreactivity in squamous epithelium of the gastrointestinal junction
Manually annotated by BRENDA team
-
expression in male, hardly detectable in female
Manually annotated by BRENDA team
-
expression in male, hardly detectable in female
Manually annotated by BRENDA team
-
expression in male, hardly detectable in female
Manually annotated by BRENDA team
-
strong isoform AKR1C3 immunoreactivity in bronchial epithelium but not in bronchial glands or alveolar pneumocytes
Manually annotated by BRENDA team
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
Manually annotated by BRENDA team
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
Manually annotated by BRENDA team
-
isozyme 17beta-HSD1
Manually annotated by BRENDA team
-
expression in male, hardly detectable in female
Manually annotated by BRENDA team
-
expression in male, hardly detectable in female
Manually annotated by BRENDA team
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
isozyme 17beta-HSD4
Manually annotated by BRENDA team
additional information
-
isoform 17beta-HSD3 shows a cytoplasmic orientation and dependence on glucose-6-phosphate dehydrogenase-generated NADPH
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31000
-
newly discovered isoenzyme, disc electrophoresis
34000
-
disc gel electrophoresis
39000
-
newly discovered isoenzyme, gel filtration
180000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 35400, sucrose density gradient centrifugation
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
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57
-
complete inactivation after 15 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
very labile enzyme, loss of activity after storage for 2 weeks at -50C
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 6 months, no loss of activity
-
0-4C, 100 mM sodium phosphate, pH 8.0, 0.05% 2-mercaptoethanol, 1 month, loss of 70% activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography on estrone-aminocaproate-Sepharose
-
ammonium sulfate, calcium phosphate gel, starch electrophoresis
-
ammonium sulfate, DEAE-cellulose, Sephadex G-100, CM-Sephadex, hydroxyapatite
-
ammonium sulfate, Sephadex G-100, DEAE-cellulose, Bio-Gel P-100
-
ammonium sulfate, Sephadex G-100, Sephadex G-75, DEAE-cellulose, hydroxyapatite, newly discovered isoenzyme and classical enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
17beta-hydroxysteroid dehydrogenase 3, expressed in human embryonic kidney 293 cells
-
expressed in LNCaP cells and in an 293-EBNA-based cell line
-
expression in Escherichia coli
-
expression in HEK-293 cell
-
expression in HeLa cell
-
expression of AKR1C3 in Eschericha coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A203V
-
inactive enzyme
E215D
-
inactive enzyme
F208I
-
inactive enzyme
M235V
-
inactive enzyme
P282L
-
inactive enzyme
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
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
S232L
-
inactive enzyme
S65L
-
inactive enzyme
V205E
-
inactive enzyme
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine