Information on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.1.1.239
-
RECOMMENDED NAME
GeneOntology No.
3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD+ = androstenedione + NADH + 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
-
-
Steroid hormone biosynthesis
-
-
Metabolic pathways
-
-
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
-
9028-62-0
-
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
mutation of Tyr118 and Phe310 in AKR1C27 to the corresponding residues (Phe and Ile, respectively) in AKR1C28 produces an enzyme that is similar to AKR1C28
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
show the reaction diagram
i.e. (R)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH
show the reaction diagram
-
i.e. (S)-tetralol
-
-
r
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
show the reaction diagram
i.e. (S)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
show the reaction diagram
i.e. (S)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
show the reaction diagram
i.e. (S)-tetralol
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
show the reaction diagram
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
show the reaction diagram
-
-
-
-
?
(S)-camphorquinone + NADH + H+
? + NAD+
show the reaction diagram
(S)-camphorquinone + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
1-acenaphthenol + NAD+
acenaphthylen-1(2H)-one + NADH + H+
show the reaction diagram
-
-
-
?
1-phenyl-1,2-propanedione + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
11alpha-hydroxytestosterone + NAD+
11alpha-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
156% velocity compared to testosterone
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
15alpha-hydroxytestosterone + NAD+
15alpha-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
131% velocity compared to testosterone
-
r
16-oxoestrone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
17beta-estradiol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
r
17beta-estradiol + NAD+
estrone + NADH + H+
show the reaction diagram
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one + NAD+
1alpha-methyl-5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
192% velocity compared to testosterone
-
r
17beta-hydroxy-5beta-androstan-3-one + NAD+
5beta-androstane-3,17-dione + NADH
show the reaction diagram
-
86% velocity compared to testosterone
-
r
2,3-butanedione + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
show the reaction diagram
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
-
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
-
-
20alpha-hydroxyprogesterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
3alpha-hydroxyprogesterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
3beta-hydroxy-5alpha-androstane-17-one + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
75% velocity compared to testosterone
-
r
3beta-hydroxyprogesterone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
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
-
-
-
-
?
4-pregnen-3alpha-ol-2-one + NAD+
4-pregnen-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
r
4-pregnen-3alpha-ol-20-one + NAD+
4-pregnen-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NAD+
5alpha-androstan-3,17 dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD+
5alpha-androstan-3alpha-ol-17-one + NADH
show the reaction diagram
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstan-3beta-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
r
5alpha-androstane-3,17-dione + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
show the reaction diagram
5alpha-androstane-3alpha,17beta-diol + NAD+
?
show the reaction diagram
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
show the reaction diagram
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
show the reaction diagram
5alpha-androstane-3beta,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH
show the reaction diagram
-
133% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NAD+
androstandione + NADH
show the reaction diagram
-
-
-
r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH
show the reaction diagram
5alpha-dihydrotestosterone + NADH + H+
testosterone + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-pregnan-20alpha-ol-3-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-pregnan-3,21alpha-diol-20-one + NAD+
5alpha-pregnan-21-ol-3,20-dione + NADH
show the reaction diagram
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
show the reaction diagram
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
show the reaction diagram
5beta-androstan-3alpha,17beta-diol + NAD+
5beta-androstan-3alpha-ol-17-one + NADH
show the reaction diagram
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
r
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
show the reaction diagram
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-androstane-17beta-ol-3-one + NAD+
5beta-abdrostan-3,17-dione + NADH + H+
show the reaction diagram
-
-
-
r
5beta-androstane-3,17-dione + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
5beta-androstane-3alpha-ol-17-one + NADH
show the reaction diagram
-
57% velocity compared to testosterone
-
r
5beta-androstane-3alpha,17beta-diol + NAD+
?
show the reaction diagram
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
show the reaction diagram
5beta-androstane-3beta,17beta-diol + NAD+
? + NAD+
show the reaction diagram
-
-
-
?
5beta-dihydrotestosterone + NAD+
androstanedione + NADH
show the reaction diagram
-
50% initial velocity compared to testosterone
-
r
5beta-dihydrotestosterone + NAD+
testosterone + NADH + H+
show the reaction diagram
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
5beta-pregnan-3alpha,21-diol-20-one + NAD+
5beta-pregnan-21-ol-3,20-dione + NADH
show the reaction diagram
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH
show the reaction diagram
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
show the reaction diagram
5beta-pregnan-3beta,21-diol-20-one + NAD+
?
show the reaction diagram
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
?
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
6beta-hydroxytestosterone + NAD+
6beta-hydroxyandrost-4-ene-3,17-dione + NADH
show the reaction diagram
-
84% velocity compared to testosterone
-
r
9,10-phenanthrenequinone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
alpha-3-hydroxyhexobarbital + NAD+
?
show the reaction diagram
-
-
-
?
alpha-tetralone + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH
show the reaction diagram
-
75% velocity compared to testosterone
-
r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
show the reaction diagram
-
-
-
-
?
androst-5-ene-3beta,17beta-diol + NAD+
androst-5-ene-3beta-ol-17-one + NADH
show the reaction diagram
-
33% velocity compared to testosterone
-
r
androstandiol + NAD+
androsterone + NADH
show the reaction diagram
-
-
-
r
androstanediol + NAD+
androsterone + NADH
show the reaction diagram
-
-
-
r
benzene dihydrodiol + NAD+
?
show the reaction diagram
-
-
-
?
benzene dihydrodiol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
beta-3-hydroxyhexobarbital + NAD+
?
show the reaction diagram
-
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
show the reaction diagram
cis-benzene dihydrodiol + NAD+
?
show the reaction diagram
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
dehydroepiandosterone + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
estradiol + NAD+
estrone + NADH
show the reaction diagram
estrone + NADPH + H+
17beta-estradiol + NADP+
show the reaction diagram
-
-
-
-
?
farnesol + NAD+
?
show the reaction diagram
-
-
-
?
farnesol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
farnesol + NAD+
farnesal + NADH + H+
show the reaction diagram
-
-
-
?
geraniol + NAD+
?
show the reaction diagram
-
-
-
?
geraniol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
geraniol + NAD+
geranial + NADH + H+
show the reaction diagram
-
-
-
?
geranylgeraniol + NAD+
?
show the reaction diagram
-
-
-
?
geranylgeraniol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
geranylgeraniol + NAD+
geranylgeranial + NADH + H+
show the reaction diagram
-
-
-
?
glycochenodeoxycholic acid + NAD+
7alpha-hydroxy-3-oxo-5-beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
?
glycolithocholic acid + NAD+
3-oxo-5beta-cholanoyl glycine + NADH
show the reaction diagram
-
-
-
?
isatin + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
lithocholic acid
5beta-cholan-3-one-24-oic acid + NADH + H+
show the reaction diagram
-
-
-
-
lithocholic acid + NAD+
5-beta-cholan-3-one-24-oic acid + NADH + H+
show the reaction diagram
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
show the reaction diagram
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH + H+
show the reaction diagram
-
-
-
?
morphine + NAD+
morphinone + NADH + H+
show the reaction diagram
reaction of EC 1.1.1.218
-
-
?
naphthalene dihydrodiol + NAD+
? + NADH + H+
show the reaction diagram
-
-
-
?
nerol + NAD+
neral + NADH + H+
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
-
-
-
-
?
pyridine-3-aldehyde + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
testosterone + NAD+
4-androstenedione + NADPH + H+
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
-
r
testosterone + NADP+
androstenedione + NADPH + H+
show the reaction diagram
-
-
-
r
trans-benzene dihydrodiol + NAD+
?
show the reaction diagram
-
-
-
?
additional information
?
-
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
5alpha-dihydrotestosterone + NAD+
androstandione + NADH
show the reaction diagram
-
-
-
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
-
-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
show the reaction diagram
-
inactivation of the anticancer drug
-
-
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
additional information
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-3-(3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)prop-2-enoate
-
-
(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-prop-2-enoic acid
-
-
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
-
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
-
-
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-(benzoyloxy)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
93.5% inhibition at 0.1 mM
(2E)-3-[4-(pyridine-4-carbonyloxy)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
-
37% inhibition at 0.010 mM
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
-
-
(E)-3-(3-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
-
-
(Z/E)-3-(4-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
-
-
(Z/E)-tert-butyl 3-(4-(3-phenylpropanoyloxy)phenyl)acrylate
-
-
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
17alpha-methyltestosterone
-
competitive inhibition
17beta-estradiol
-
0.175 mM, 25-40% inhibition of testosterone oxidation
2'-des-methyl-indomethacin
-
the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
-
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-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
-
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
-
-
21-hydroxypregn-4-ene-3,20-dione
-
0.010 mM, 73% inhibition
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-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic acids
-
-
-
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
-
-
3-(phenylamino)benzoic acid
-
-
-
3-phenoxybenzoic acid
-
inhibitor carboxylic acid binds to the oxyanion site, in which the carboxylate group very closely overlays the acetate molecule found in other AKR1C3 structures and forms hydrogen bonds to the enzyme catalytic residues His117 and Tyr55, as well as to a conserved water network located in and near the SP3 subpocket. The 3-phenoxy ring extends into the SP1 subpocket and makes van der Waals contacts with the aromatic residues Phe306, Phe311 and Tyr319 that line the pocket
3-[(4-nitrophenyl)amino]benzoic acid
-
94fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
-
-
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
3beta-cyclohexylethyl-androsterone
-
potent inhibitor
3beta-n-hexyl-androsterone
-
potent inhibitor
3beta-phenylethyl-androsterone
-
potent inhibitor
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
-
-
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
-
-
5alpha-Androstan-3beta-ol-17-one
-
0.005 mM, 55% inhibition
5alpha-pregnan-3beta-ol-20-one
-
0.005 mM, 52% inhibition
5beta-androstan-3,17-dione
-
product inhibition, forward reaction
5beta-androstan-3beta-ol-17-one
-
0.005 mM, 87% inhibition
5beta-dihydrotestosterone
-
product inhibition, reverse reaction
5beta-Pregnan-3beta-ol-20-one
-
0.005 mM, 81% inhibition
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
7-hydroxyflavone
-
0.007 mM, 50% inhibition, oxidation of androstandiol
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
-
-
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
-
-
abietic acid
-
0.010 mM, 50% inhibition, oxidation of androstandiol
Ag+
-
0.1 mM, complete inhibition
androstendione
-
-
baccharin
-
-
-
biochain A
-
0.014 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.008 mM, oxidation of androstanediol
chrysin
-
0.010 mM, 50% inhibition, oxidation of androstandiol
Cibacron blue
-
-
coumestrol
-
0.005 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.011 mM, 50% inhibition, oxidation of androstanediol
CuCl2
-
1 mM, complete inhibition
dexamethasone
-
0.10 mM, 39% inhibition
Dienstrol
-
0.010 mM, 60% inhibition
FeCl3
-
10 mM, 46% inhibition
ferulic acid
-
-
Hexestrol
Hexoestrol
Hg2+
-
0.1 mM, complete inhibition
hinokitiol
ikarisoside A
competitive; competitive
-
indomethacin
kaempferol
m-coumaric acid
-
-
Medroxyprogesterone acetate
-
0.010 mM, 22% inhibition
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
-
-
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
-
-
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
-
-
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
-
-
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 acids
-
-
-
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
NaCN
-
1 mM, 50% inhibition
naringenin
-
0.010 mM, 50% inhibition, oxidation of androstandiol
noranhydroicaritin
-
-
p-chloromercuribenzoate
-
0.1 mM, complete inhibition
p-coumaric acid
-
-
Phenolphthalein
quercetin
Sodium amytal
-
10 mM, 25% inhibition
stilboestrol
-
0.010 mM, 61% inhibition
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
thiazolidinedione
-
-
Triton X-100
-
immediate loss of 60-70% activity, remaining activity is stable for 4 days, competitive vs. testosterone, non-competitive vs. NAD+
zearalenone
ZnCl2
-
10 mM, 10% inhibition
[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
0.095
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.004 - 0.25
(S)-1,2,3,4-tetrahydro-1-naphthol
0.014 - 0.181
(S)-1-indanol
0.0019 - 0.0067
(S)-camphorquinone
-
0.148
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
0.0008 - 0.005
1-phenyl-1,2-propanedione
0.0021 - 0.01
16-oxoestrone
0.0021 - 0.1
17beta-estradiol
0.19 - 0.371
2,3-Butanedione
0.035 - 0.67
2-Cyclohexen-1-ol
0.0031
4-oxo-2-nonenal
-
pH 7.4, 25°C
0.0057 - 0.081
4-pregnen-3alpha-ol-20-one
-
0.00067 - 0.13
5alpha-androstan-17beta-ol-3-one
0.0031
5alpha-androstan-3alpha,17beta-diol
-
-
0.0022 - 0.0092
5alpha-Androstan-3alpha-ol-17-one
0.0005 - 0.0078
5alpha-androstane-3alpha,17beta-diol
0.00067 - 0.0035
5alpha-pregnan-3alpha-ol-20-one
0.00067 - 0.03
5beta-androstan-17beta-ol-3-one
0.0066
5beta-androstan-3,17-dione
-
-
0.0048
5beta-Androstan-3alpha,17beta-diol
-
-
0.0015 - 0.0023
5beta-Androstan-3alpha-ol-17-one
0.0022 - 0.02
5beta-androstane-3alpha,17beta-diol
0.0038
5beta-pregnan-3,20-dione
-
-
0.0062
5beta-pregnan-3alpha,17beta-diol-20-one
-
-
0.0036 - 0.17
5beta-Pregnan-3alpha-ol-20-one
0.0021 - 0.101
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
0.0001 - 0.0002
9,10-phenanthrenequinone
0.03
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.0038 - 0.15
alpha-tetralone
0.0016
androst-4-ene-3,17-dione
-
-
0.024
androstendione
-
reduction of androstendione, pH 7.0
0.027 - 1.11
benzene dihydrodiol
0.013
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.0006 - 0.0097
beta-ionol
-
0.63
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.009
estrone
-
pH 7.0, 37°C
0.00074 - 0.011
farnesol
0.0042 - 0.57
geraniol
0.0007 - 0.0012
geranylgeraniol
0.0075
glycochenodeoxycholic acid
-
-
0.003
glycolithocholic acid
-
-
0.0005 - 0.0011
isatin
0.0005 - 0.14
lithocholic acid
0.52
morphine
pH 7.4, 25°C
0.0068 - 0.27
NAD+
0.0026 - 0.033
NADH
1.38
NADP+
pH 7.4, 25°C, with substrate S-camphorquinone
0.027
Naphthalene dihydrodiol
pH 7.4, 25°C
0.162
nerol
pH 7.4, 25°C, recombinant enzyme
0.29 - 1.1
Pyridine-3-aldehyde
0.0016 - 0.25
testosterone
1
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0075
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.042 - 0.367
(S)-1,2,3,4-tetrahydro-1-naphthol
0.039 - 0.4
(S)-1-indanol
0.183 - 0.98
(S)-camphorquinone
-
0.283
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
0.155 - 0.45
1-phenyl-1,2-propanedione
0.157 - 0.867
16-oxoestrone
0.0063 - 0.0217
17beta-estradiol
0.118 - 0.55
2,3-Butanedione
0.028 - 0.16
2-Cyclohexen-1-ol
0.148
4-oxo-2-nonenal
-
pH 7.4, 25°C
0.0014 - 0.012
4-pregnen-3alpha-ol-20-one
-
0.0052 - 0.065
5alpha-androstan-17beta-ol-3-one
0.45
5alpha-androstan-3alpha,17beta-diol
-
-
0.0033 - 0.058
5alpha-Androstan-3alpha-ol-17-one
0.0027 - 0.055
5alpha-androstane-3alpha,17beta-diol
0.267
5alpha-Pregnan-3alpha,21-diol-20-one
-
-
0.0012 - 0.0072
5alpha-pregnan-3alpha-ol-20-one
0.002 - 0.367
5beta-androstan-17beta-ol-3-one
0.167
5beta-androstan-3,17-dione
-
-
0.85
5beta-Androstan-3alpha,17beta-diol
-
-
0.0023 - 0.052
5beta-Androstan-3alpha-ol-17-one
0.004 - 0.0122
5beta-androstane-3alpha,17beta-diol
0.158
5beta-pregnan-3,20-dione
-
-
0.367
5beta-Pregnan-3alpha,21-diol-20-one
-
-
0.005 - 0.233
5beta-Pregnan-3alpha-ol-20-one
0.052 - 0.108
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
0.152 - 0.617
9,10-phenanthrenequinone
0.04
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.0143 - 0.2
alpha-tetralone
0.088 - 0.29
benzene dihydrodiol
0.0967
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.0075 - 0.053
beta-ionol
-
0.032
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.0011
estrone
-
pH 7.0, 37°C
0.0045 - 0.027
farnesol
0.015 - 0.028
geraniol
0.0008 - 0.038
geranylgeraniol
0.02
glycochenodeoxycholic acid
-
-
0.25
glycolithocholic acid
-
-
0.183 - 0.65
isatin
0.00067 - 0.05
lithocholic acid
0.49
morphine
pH 7.4, 25°C
0.004 - 0.283
NAD+
0.123 - 0.683
NADH
0.0917
NADP+
pH 7.4, 25°C, with substrate S-camphorquinone
0.067
Naphthalene dihydrodiol
pH 7.4, 25°C
0.115
nerol
pH 7.4, 25°C, recombinant enzyme
0.025 - 0.2
Pyridine-3-aldehyde
0.0079 - 0.417
testosterone
0.045
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.083
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
1.67
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.55
(S)-1-indanol
pH 7.4, 25°C, recombinant enzyme
1.83
1-Acenaphthenol
pH 7.4, 25°C, recombinant enzyme
0.05
2-Cyclohexen-1-ol
pH 7.4, 25°C, recombinant enzyme
47.8
4-oxo-2-nonenal
-
pH 7.4, 25°C
2.17
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
7.5
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
5.3
beta-ionol
pH 7.4, 25°C, recombinant enzyme
-
0.05
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.127
estrone
-
pH 7.0, 37°C
0.42
farnesol
pH 7.4, 25°C, recombinant enzyme
0.2
geraniol
pH 7.4, 25°C, recombinant enzyme
33.3
geranylgeraniol
pH 7.4, 25°C, recombinant enzyme
2
NAD+
pH 7.4, 25°C, with substrate S-tetralol
12.67
NADH
pH 7.4, 25°C, with substrate S-camphorquinone
0.067
NADP+
pH 7.4, 25°C, with substrate S-camphorquinone
0.067
nerol
pH 7.4, 25°C, recombinant enzyme
0.05
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
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
0.0029
Hexestrol
pH 7.4, 25°C, recombinant enzyme
0.00056
hinokitiol
pH 7.4, 25°C, recombinant enzyme
0.000024
ikarisoside A
pH 7.4, 25°C, recombinant enzyme
-
0.0007
noranhydroicaritin
pH 7.4, 25°C, recombinant enzyme
-
0.00038
quercitrin
pH 7.4, 25°C, recombinant enzyme
0.003
zearalenone
pH 7.4, 25°C, recombinant enzyme
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
0.009 - 0.073
Hexestrol
0.002 - 0.042
hinokitiol
0.017 - 0.05
icarisid II
-
0.00013 - 0.02
ikarisoside A
-
0.0001
indomethacin
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.015 - 0.02
kaempferol
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
0.0022 - 0.015
noranhydroicaritin
-
0.199
p-coumaric acid
Homo sapiens
-
pH 7.0, 37°C
0.00065 - 0.02
Phenolphthalein
0.012 - 0.026
quercetin
0.0024 - 0.04
quercitrin
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
0.0091 - 0.05
zearalenone
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
0.000176
-
enzyme activity in hepatic cytosol
0.00035
-
enzyme activity in hepatic cytosol
0.00044
-
enzyme activity in hepatic cytosol
0.0007
-
enzyme activity in hepatic microsomes
0.00168
-
enzyme activity in hepatic microsomes
0.00283
-
enzyme activity in hepatic microsomes
0.01794
-
enzyme activity in hepatic microsomes
22.3
-
microsomal activitiy
additional information
-
0.046 micromol min/g liver, microsomes, substrate 5alpha-dihydrotestosterone, coenzyme NADP+; 0.086 micromol min/g liver, microsomes, substrate testosterone, coenzyme NADP+; 0.144 micromol min/g liver, microsomes, substrate 5beta-dihydrotestosterone, coenzyme NADP+; 0.1556 micromol min/g liver, microsomes, substrate 5alpha-dihydrotestosterone, coenzyme NAD+; 0.186 micromol min/g liver, microsomes, substrate testosterone, coenzyme NAD+; 0.388 micromol min/g liver, microsomes, substrate 5beta-dihydrotestosterone, coenzyme NAD+
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.3
-
-
8.5 - 9.5
-
-
9 - 10
-
oxidation of testosterone, equal velocity of oxidation and reduction at pH 8.0
9.5
-
solubilized and membrane bound enzyme
9.5 - 10
NAD+-linked (S)-tetralol dehydrogenase activity; NAD+-linked (S)-tetralol dehydrogenase activity; NAD+-linked (S)-tetralol dehydrogenase activity
9.6
-
sharp drop above
10.4
-
oxidation of 5beta-androstan-3alpha,17beta-diol
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
-
-
6 - 9.5
-
sharp decrease above pH 10.0
8 - 9.6
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 40
-
-
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
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
in female hamsters
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
high expression level of AKR1C26
Manually annotated by BRENDA team
additional information