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Information on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+) and Organism(s) Homo sapiens

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IUBMB Comments
Also acts on other 17beta-hydroxysteroids and on the 3alpha-hydroxy group of pregnanes and bile acids. Different from EC 1.1.1.50 3alpha-hydroxysteroid dehydrogenase (Si-specific) or EC 1.1.1.213 3alpha-hydroxysteroid dehydrogenase (Re-specific).
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
The taxonomic range for the selected organisms is: Homo sapiens
Synonyms
17beta-hsd, aldo-keto reductase 1c3, type 5 17beta-hsd, 17beta-hydroxysteroid dehydrogenase type 5, 17-ketoreductase, type 3 17beta-hydroxysteroid dehydrogenase, type 5 17beta-hydroxysteroid dehydrogenase, type 2 3alpha-hsd, akr1c28, 3alpha(17beta)-hsd, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
17-ketoreductase
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-
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-
17beta-HSD
-
-
-
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17beta-hydroxysteroid dehydrogenase type 5
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3alpha(17beta)-HSD
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-
-
-
AKR1C3
aldo-keto reductase 1C3
dehydrogenase, 3alpha,17beta-hydroxy steroid
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-
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type 2 3alpha-HSD
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type 2 3alpha-hxdroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase
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type 3 17beta-hydroxysteroid dehydrogenase
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type 5 17beta-HSD
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type 5 17beta-hydroxysteroid dehydrogenase
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type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase
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type 5 beta-hydroxysteroid dehydrogenase
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additional information
cf. EC 1.1.1.357
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3alpha(or 17beta)-hydroxysteroid:NAD+ oxidoreductase
Also acts on other 17beta-hydroxysteroids and on the 3alpha-hydroxy group of pregnanes and bile acids. Different from EC 1.1.1.50 3alpha-hydroxysteroid dehydrogenase (Si-specific) or EC 1.1.1.213 3alpha-hydroxysteroid dehydrogenase (Re-specific).
CAS REGISTRY NUMBER
COMMENTARY hide
126469-82-7
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9028-62-0
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH
show the reaction diagram
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i.e. (S)-tetralol
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-
r
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
show the reaction diagram
-
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
-
-
r
2-[(2-bromoethyl)(2-[[(2-hydroxyethyl)amino]methyl]-4,6-dinitrophenyl)amino]ethyl methanesulfonate + 2 NADH + 2 H+
2-[(2-bromoethyl)[4-(hydroxyamino)-2-[[(2-hydroxyethyl)amino]methyl]-6-nitrophenyl]amino]ethyl methanesulfonate + 2 NAD+ + H2O
show the reaction diagram
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i.e. PR-104A, phosphate ester prodrug designed to exploit tumor hypoxia
i.e. PR-104H, enzyme acts as nitroreductase for activation of PR-104A
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4-androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
-
-
-
-
?
4-oxo-2-nonenal + NADPH + H+
4-hydroxy-2-nonenal + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NAD+
androstandione + NADH
show the reaction diagram
-
-
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r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH
show the reaction diagram
-
-
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r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
show the reaction diagram
-
-
-
-
?
androstandiol + NAD+
androsterone + NADH
show the reaction diagram
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r
androstanediol + NAD+
androsterone + NADH
show the reaction diagram
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-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
estradiol + NAD+
estrone + NADH
show the reaction diagram
-
-
-
r
estrone + NADPH + H+
17beta-estradiol + NADP+
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin D2 + NADPH + H+
9alpha,11beta-prostaglandin F2 + NADP+
show the reaction diagram
-
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
testosterone + NAD+
androstenedione + NADH + H+
show the reaction diagram
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
show the reaction diagram
-
NADP is 3fold less efficient as cofactor
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r
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5alpha-dihydrotestosterone + NAD+
androstandione + NADH
show the reaction diagram
-
-
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r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
show the reaction diagram
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-
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-
?
androstandiol + NAD+
androsterone + NADH
show the reaction diagram
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r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
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inactivation of the anticancer drug
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r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
show the reaction diagram
testosterone + NAD+
androstenedione + NADH + H+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-3-(3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)prop-2-enoate
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(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
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93.3% inhibition at 0.1 mM
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
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89.1% inhibition at 0.1 mM
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
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92.7% inhibition at 0.1 mM
(2E)-3-prop-2-enoic acid
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(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
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(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
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i.e. baccharin, a component of Brazilian propolis, exhibits a high inhibitory potency and selectivity for AKR1C3 over other AKR1C isoforms. When the cinnamic acid group of baccharin is esterified, there is a dramatic decrease in potency and selectivity for AKR1C3 in comparison to baccharin. Low or submicromolar inhibition is observed when the 3-prenyl group of baccharin is removed, and the selectivity over AKR1C2 is low. Inhibition of NAD+ dependent oxidation of S-tetralol
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
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(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
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(2E)-3-[4-(benzoyloxy)phenyl]prop-2-enoic acid
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(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
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93.5% inhibition at 0.1 mM
(2E)-3-[4-(pyridine-4-carbonyloxy)phenyl]prop-2-enoic acid
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(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
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37% inhibition at 0.010 mM
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
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(E)-3-(3-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
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(Z/E)-3-(4-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
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(Z/E)-tert-butyl 3-(4-(3-phenylpropanoyloxy)phenyl)acrylate
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1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
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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
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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
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IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM
2'-des-methyl-indomethacin
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the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
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2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
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inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
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2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
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2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
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2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
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3-((4-nitronaphthalen-1-yl)amino)benzoic acid
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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-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoate
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3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
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3-(phenylamino)benzoic acid
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3-phenoxybenzoic acid
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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
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94fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
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3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
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3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
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3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
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3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
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3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
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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
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inhibitor shows 17fold and 30fold selectivity against isoforms AKR1C2 and AKR1C1, respectively, and much higher selectivity against AKR1C4
3beta-cyclohexylethyl-androsterone
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potent inhibitor
3beta-n-hexyl-androsterone
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potent inhibitor
3beta-phenylethyl-androsterone
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potent inhibitor
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
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5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
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5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
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5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
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6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
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7-hydroxyflavone
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0.007 mM, 50% inhibition, oxidation of androstandiol
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
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9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
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9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
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abietic acid
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0.010 mM, 50% inhibition, oxidation of androstandiol
baccharin
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biochain A
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0.014 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.008 mM, oxidation of androstanediol
chrysin
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0.010 mM, 50% inhibition, oxidation of androstandiol
coumestrol
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0.005 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.011 mM, 50% inhibition, oxidation of androstanediol
ferulic acid
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-
indomethacin
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-
kaempferol
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0.008 mM, 50% inhibition, oxidation of androstandiol
m-coumaric acid
-
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methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
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-
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
-
-
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
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methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
-
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methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
-
-
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
-
-
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-(4-chlorobenzoyl)-melatonin
-
-
N-benzoylanthranilic acid
-
-
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
naringenin
-
0.010 mM, 50% inhibition, oxidation of androstandiol
p-coumaric acid
-
-
quercetin
-
0.009 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.005 mM, oxidation of androstanediol
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
thiazolidinedione
-
-
zearalenone
-
0.004 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.002 mM, oxidation of androstanediol
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
-
-
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
-
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
-
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
-
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0031
4-oxo-2-nonenal
-
pH 7.4, 25°C
0.009
estrone
-
pH 7.0, 37°C
0.1
NAD+
-
solubilized enzyme
0.0016
testosterone
-
solubilized enzyme
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.148
4-oxo-2-nonenal
-
pH 7.4, 25°C
0.0011
estrone
-
pH 7.0, 37°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
47.8
4-oxo-2-nonenal
-
pH 7.4, 25°C
0.127
estrone
-
pH 7.0, 37°C
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
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.021
(2E)-3-(3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
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
0.0047
(2E)-3-prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0001
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0086
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.00044
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0063
(2E)-3-[4-(benzoyloxy)phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
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
0.068
(2E)-3-[4-(pyridine-4-carbonyloxy)phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0097
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.00356
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00096
(E)-3-(3-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
Homo sapiens
-
pH 7.0, 37°C
0.0023
(Z/E)-3-(4-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
Homo sapiens
-
pH 7.0, 37°C
0.632
(Z/E)-tert-butyl 3-(4-(3-phenylpropanoyloxy)phenyl)acrylate
Homo sapiens
-
pH 7.0, 37°C
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
0.000213
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.00882
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00111
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00786
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0058
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0124
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00252
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00373
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.012
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00119
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00021
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00265
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00634
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00207
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00074
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH 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
0.1
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
Homo sapiens
-
above, 100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.000036
3-[(4-nitrophenyl)amino]benzoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00015
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00007 - 0.00009
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
0.00029
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00022
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00012
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00029
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00325
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00311
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00553
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00034
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00254
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00144
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00469
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0025
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00111
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00013
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH 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
0.00015
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
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
0.0024
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.000279
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00034
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00016
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00507
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.021
ferulic acid
Homo sapiens
-
pH 7.0, 37°C
0.0001
indomethacin
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.086
m-coumaric acid
Homo sapiens
-
pH 7.0, 37°C
0.02278
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.01134
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00564
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00224 - 0.00759
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
0.00754 - 0.01571
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
0.00209
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00265
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00397
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00194
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.199
p-coumaric acid
Homo sapiens
-
pH 7.0, 37°C
607
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.0005
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00025
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00096
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00007
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00496
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00071
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00012
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00223
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00014
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00521
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00108
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00016
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00244
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00027
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00044
-
enzyme activity in hepatic cytosol
0.00168
-
enzyme activity in hepatic microsomes
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
7.4
-
assay at
8.5 - 9.5
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high level
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
-
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
-
high level
Manually annotated by BRENDA team
-
pre- and peri-pubertal changes promote expression of the enzyme in Leydig cells
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
-
in contrast to the normal adult testis, the pediatric cryptorchid testis shows AKR1C3 expression in 18%-26% of Sertoli cells in patients at Tanner stages 2 and beyond
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
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
the enzyme is a member of the aldo-keto reductase (AKR) superfamily that metabolizes endogenous substrates, such as carbohydrates, prostaglandins and steroids, and xenobiotics in a NAD(P)(H)-dependent manner
physiological function
additional information
-
the structure of the AKR1C3-NADP+ complex is solved by molecular replacement, overview
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
AK1C3_HUMAN
323
0
36853
Swiss-Prot
DHB2_HUMAN
387
2
42785
Swiss-Prot
H17B6_HUMAN
317
0
35966
Swiss-Prot
DHB8_HUMAN
261
0
26974
Swiss-Prot
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, with an estimated free energy of binding of ?5 kcal/mol
-
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
-
NADP+ and 2'-des-methyl-indomethacin is determined at a resolution of 1.8 A by molecular replacement. The cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 50 mM Tris-HCl, pH 9.0, 20% glycerol, 100 mM KCl, 5 mg/ml N-octyl glucoside, 24 h, 20% loss of activity, -20°C, 1 week, no loss of activity
-
PURIFICATION/commentary
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme
-
CLONED/commentary
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
-
expressed in HeLa human cervical carcinoma cells and COS-1 monkey kidney tumor cells
-
expression in Escherichia coli
-
expression in MCF-7 cell
-
gene AKR1C3, real-time PCR expression anaysis
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
AKR1C3 expression occurs in a Tanner stage dependent-fashion
-
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
-
marked upregulation of AKR1C3 is found in a subset including hepatocellular, bladder, renal, gastric, and non-small cell lung carcinoma
-
the enzyme expression is upregulated by daunorubicin treament
-
the expression of isoform AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Krazeisen, A.; Breitling, R.; Möller, G.; Adamski, J.
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5
Mol. Cell. Endocrinol.
171
151-162
2001
Homo sapiens
Manually annotated by BRENDA team
Stupans, I.; Kong, S.; Kirlich, S.; McKinnon, R.A.; Murray, M.
Testosterone dehydrogenase activity in koala liver: characterization of cofactor and steroid substrate differences
Comp. Biochem. Physiol. B
125
245-250
2000
Homo sapiens, Notamacropus eugenii, Phascolarctos cinereus, Rattus norvegicus
Manually annotated by BRENDA team
Carre, J.L.; Quemener, E.; Amet, Y.; Simon, B.; Berthou, F.; Mangin, P.; Floch, H.H.; Abalain, J.H.
Characterization and solubization of testosterone 17beta-hydroxysteroid dehydrogenase in human hyperplastic prostate
J. Steroid Biochem. Mol. Biol.
46
265-267
1993
Homo sapiens
Manually annotated by BRENDA team
Dumont, M.; Luu-The, V.; de Lanoit, Y.; Labrie, F.
Expression of human 17beta-hydroxysteroid dehydrogenase in mammalian cells
J. Steroid Biochem. Mol. Biol.
41
605-608
1992
Homo sapiens
Manually annotated by BRENDA team
Ngatcha, B.T.; Laplante, Y.; Labrie, F.; Luu-The, V.; Poirier, D.
3beta-Alkyl-androsterones as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: inhibitory potency in intact cells, selectivity towards isoforms 1, 2, 5 and 7, binding affinity for steroid receptors, and proliferative/antiproliferative activities on AR+ and ER+ cell lines
Mol. Cell. Endocrinol.
248
225-232
2006
Homo sapiens
Manually annotated by BRENDA team
Fung, K.M.; Samara, E.N.; Wong, C.; Metwalli, A.; Krlin, R.; Bane, B.; Liu, C.Z.; Yang, J.T.; Pitha, J.V.; Culkin, D.J.; Kropp, B.P.; Penning, T.M.; Lin, H.K.
Increased expression of type 2 3alpha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3) and its relationship with androgen receptor in prostate carcinoma
Endocr. Relat. Cancer
13
169-180
2006
Homo sapiens
Manually annotated by BRENDA team
Azzarello, J.; Fung, K.M.; Lin, H.K.
Tissue distribution of human AKR1C3 and rat homolog in adult genitourinary system
J. Histochem. Cytochem.
56
853-861
2008
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Guise, C.P.; Abbattista, M.R.; Singleton, R.S.; Holford, S.D.; Connolly, J.; Dachs, G.U.; Fox, S.B.; Pollock, R.; Harvey, J.; Guilford, P.; Donate, F.; Wilson, W.R.; Patterson, A.V.
The bioreductive prodrug PR-104A is activated under aerobic conditions by human aldo-keto reductase 1C3
Cancer Res.
70
1573-1584
2010
Homo sapiens
Manually annotated by BRENDA team
Nakamura, Y.; Hornsby, P.; Casson, P.; Morimoto, R.; Satoh, F.; Xing, Y.; Kennedy, M.; Sasano, H.; Rainey, W.
Type 5 17ß-hydroxysteroid dehydrogenase (AKR1C3) contributes to testosterone production in the adrenal reticularis
J. Clin. Endocrinol. Metab.
94
2192-2198
2009
Homo sapiens
Manually annotated by BRENDA team
Byrns, M.C.; Duan, L.; Lee, S.H.; Blair, I.A.; Penning, T.M.
Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer
J. Steroid Biochem. Mol. Biol.
118
177-187
2010
Homo sapiens
Manually annotated by BRENDA team
Ashley, R.A.; Yu, Z.; Fung, K.M.; Frimberger, D.; Kropp, B.P.; Penning, T.M.; Lin, H.K.
Developmental evaluation of aldo-keto reductase 1C3 expression in the cryptorchid testis
Urology
76
67-72
2010
Homo sapiens
Manually annotated by BRENDA team
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, Homo sapiens (P42330)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
Liedtke, A.J.; Adeniji, A.O.; Chen, M.; Byrns, M.C.; Jin, Y.; Christianson, D.W.; Marnett, L.J.; Penning, T.M.
Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer
J. Med. Chem.
56
2429-2446
2013
Homo sapiens (P42330)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
Matsunaga, T.; Yamaguchi, A.; Morikawa, Y.; Kezuka, C.; Takazawa, H.; Endo, S.; El-Kabbani, O.; Tajima, K.; Ikari, A.; Hara, A.
Induction of aldo-keto reductases (AKR1C1 and AKR1C3) abolishes the efficacy of daunorubicin chemotherapy for leukemic U937 cells
Anticancer Drugs
25
868-877
2014
Homo sapiens (P42330)
Manually annotated by BRENDA team
Zang, T.; Verma, K.; Chen, M.; Jin, Y.; Trippier, P.C.; Penning, T.M.
Screening baccharin analogs as selective inhibitors against type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3)
Chem. Biol. Interact.
234
339-348
2015
Homo sapiens (P42330)
Manually annotated by BRENDA team
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