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show all sequences of 1.1.1.239

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

Liedtke, A.J.; Adeniji, A.O.; Chen, M.; Byrns, M.C.; Jin, Y.; Christianson, D.W.; Marnett, L.J.; Penning, T.M.; J. Med. Chem. 56, 2429-2446 (2013)

Data extracted from this reference:

Crystallization (Commentary)
Crystallization
Organism
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
Homo sapiens
Inhibitors
Inhibitors
Commentary
Organism
Structure
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
-
Homo sapiens
2'-des-methyl-indomethacin
the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
Homo sapiens
3-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoate
-
Homo sapiens
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
-
Homo sapiens
3-(phenylamino)benzoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
-
Homo sapiens
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
-
Homo sapiens
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
-
Homo sapiens
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
-
Homo sapiens
baccharin
-
Homo sapiens
indomethacin
-
Homo sapiens
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
-
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
-
Homo sapiens
additional information
development of potent and selective indomethacin analogues for the inhibition of AKR1C3 in castrate-resistant prostate cancer, overview. Increasing the length of the aliphatic side chain of indomethacin from -ethyl to -propyl leads to a 2fold reduction in AKR1C3 potency, but the compound retained 257fold selectivity for AKR1C3 over AKR1C2
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
-
Homo sapiens
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
N-(4-chlorobenzoyl)-melatonin
-
Homo sapiens
N-benzoylanthranilic acid
-
Homo sapiens
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
thiazolidinedione
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
testosterone + NAD+
Homo sapiens
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
androstenedione + NADH + H+
-
-
r
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Homo sapiens
P42330
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
LNCaP cell
-
Homo sapiens
-
prostate cancer cell
-
Homo sapiens
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
testosterone + NAD+
-
725674
Homo sapiens
androstenedione + NADH + H+
-
-
-
r
testosterone + NAD+
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
725674
Homo sapiens
androstenedione + NADH + H+
-
-
-
r
Cofactor
Cofactor
Commentary
Organism
Structure
NAD+
-
Homo sapiens
NADH
-
Homo sapiens
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00007
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
0.00007
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
0.00009
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
0.0001
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
indomethacin
0.00012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
0.00012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
0.00013
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
0.00014
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
0.00015
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
0.00015
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
0.00016
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
0.00016
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
0.00021
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
0.00022
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
0.00025
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
0.00027
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.000279
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
0.00029
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
0.00029
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
0.00034
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
0.00034
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
0.0005
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
0.00071
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
0.00074
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
0.00096
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
0.00108
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00111
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
0.00111
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
0.00119
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
0.00144
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
0.00194
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00207
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
0.00209
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00223
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00224
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
0.0024
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
0.00244
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.0025
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
0.00252
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
0.00254
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
0.00265
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
0.00265
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
0.00311
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
0.00325
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
0.00356
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
0.00373
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
0.00397
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00469
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
0.00496
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
0.00507
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
0.00521
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00553
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
0.00564
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
0.0058
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
0.00634
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
0.00754
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
0.00759
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
0.00786
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
0.00882
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
0.01134
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
0.012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
0.0124
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
0.01571
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
0.02278
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
0.1
-
above, 100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NAD+
-
Homo sapiens
NADH
-
Homo sapiens
Crystallization (Commentary) (protein specific)
Crystallization
Organism
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
Homo sapiens
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00007
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
0.00007
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
0.00009
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
0.0001
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
indomethacin
0.00012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
0.00012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
0.00013
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
0.00014
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
0.00015
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
0.00015
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
0.00016
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
0.00016
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
0.00021
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
0.00022
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
0.00025
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
0.00027
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.000279
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
0.00029
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
0.00029
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
0.00034
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
0.00034
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
0.0005
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
0.00071
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
0.00074
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
0.00096
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
0.00108
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00111
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
0.00111
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
0.00119
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
0.00144
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
0.00194
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00207
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
0.00209
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00223
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00224
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
0.0024
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
0.00244
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.0025
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
0.00252
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
0.00254
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
0.00265
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
0.00265
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
0.00311
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
0.00325
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
0.00356
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
0.00373
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
0.00397
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
0.00469
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
0.00496
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
0.00507
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
0.00521
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
0.00553
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
0.00564
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
0.0058
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
0.00634
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
0.00754
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
0.00759
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
0.00786
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
0.00882
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
0.01134
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
0.012
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
0.0124
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
0.01571
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
0.02278
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
0.1
-
above, 100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
Homo sapiens
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
-
Homo sapiens
2'-des-methyl-indomethacin
the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
Homo sapiens
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
Homo sapiens
3-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoate
-
Homo sapiens
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
-
Homo sapiens
3-(phenylamino)benzoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
-
Homo sapiens
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
-
Homo sapiens
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
-
Homo sapiens
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
-
Homo sapiens
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
Homo sapiens
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
-
Homo sapiens
baccharin
-
Homo sapiens
indomethacin
-
Homo sapiens
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
-
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
-
Homo sapiens
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
-
Homo sapiens
additional information
development of potent and selective indomethacin analogues for the inhibition of AKR1C3 in castrate-resistant prostate cancer, overview. Increasing the length of the aliphatic side chain of indomethacin from -ethyl to -propyl leads to a 2fold reduction in AKR1C3 potency, but the compound retained 257fold selectivity for AKR1C3 over AKR1C2
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
-
Homo sapiens
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
N-(4-chlorobenzoyl)-melatonin
-
Homo sapiens
N-benzoylanthranilic acid
-
Homo sapiens
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
Homo sapiens
thiazolidinedione
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
Homo sapiens
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
testosterone + NAD+
Homo sapiens
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
androstenedione + NADH + H+
-
-
r
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
LNCaP cell
-
Homo sapiens
-
prostate cancer cell
-
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
testosterone + NAD+
-
725674
Homo sapiens
androstenedione + NADH + H+
-
-
-
r
testosterone + NAD+
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
725674
Homo sapiens
androstenedione + NADH + H+
-
-
-
r
General Information
General Information
Commentary
Organism
additional information
the structure of the AKR1C3-NADP+ complex is solved by molecular replacement, overview
Homo sapiens
physiological function
AKR1C3 catalyzes the conversion of the weak androgen precursors 4-androstene-3,17-dione and 5alpha-androstane-3,17-dione to the potent androgens testosterone and 5alpha-dihydrotestosterone (DHT), respectively, and is one of the most highly upregulated genes in castrate-resistant prostate cancer, CRPC
Homo sapiens
General Information (protein specific)
General Information
Commentary
Organism
additional information
the structure of the AKR1C3-NADP+ complex is solved by molecular replacement, overview
Homo sapiens
physiological function
AKR1C3 catalyzes the conversion of the weak androgen precursors 4-androstene-3,17-dione and 5alpha-androstane-3,17-dione to the potent androgens testosterone and 5alpha-dihydrotestosterone (DHT), respectively, and is one of the most highly upregulated genes in castrate-resistant prostate cancer, CRPC
Homo sapiens
Other publictions for EC 1.1.1.239
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
740293
Zang
Screening baccharin analogs as ...
Homo sapiens
Chem. Biol. Interact.
234
339-348
2015
-
-
-
-
-
-
17
-
-
-
-
1
-
2
-
-
-
-
-
-
-
-
2
-
1
-
-
-
1
-
-
2
-
-
15
-
-
-
2
-
-
-
15
17
-
-
-
-
-
1
-
-
-
-
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
1
1
-
-
-
740637
Endo
Characterization of hamster NA ...
Mesocricetus auratus
J. Biochem.
158
425-434
2015
-
-
1
-
-
-
4
18
1
-
1
-
-
1
-
-
1
-
-
8
-
-
43
1
1
-
-
17
1
-
-
5
-
-
3
-
-
1
5
-
-
-
3
4
-
18
1
-
1
-
-
-
-
1
-
8
-
-
43
1
1
-
-
17
1
-
-
-
-
2
2
-
17
17
739864
Matsunaga
Induction of aldo-keto reducta ...
Homo sapiens
Anticancer Drugs
25
868-877
2014
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
6
-
-
2
-
1
-
-
-
1
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
6
-
-
2
-
1
-
-
-
1
-
-
-
1
2
2
1
-
-
724719
Matsunaga
Pathophysiological roles of al ...
Homo sapiens
Chem. Biol. Interact.
202
234-242
2013
-
1
-
-
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
2
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
1
-
-
-
-
1
1
1
1
1
1
724915
Heinrich
Synthesis and structure-activi ...
Homo sapiens
Eur. J. Med. Chem.
62
738-744
2013
-
-
-
1
-
-
3
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
1
-
-
3
3
-
-
-
-
-
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
724916
Gazvoda
2,3-diarylpropenoic acids as s ...
Homo sapiens
Eur. J. Med. Chem.
62
89-97
2013
-
-
-
1
-
-
4
-
-
-
-
-
-
1
-
-
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-
-
-
-
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-
-
-
-
-
-
-
-
-
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-
-
4
-
-
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-
1
-
-
4
4
-
-
-
-
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
725674
Liedtke
Development of potent and sele ...
Homo sapiens
J. Med. Chem.
56
2429-2446
2013
-
-
-
1
-
-
71
-
-
-
-
1
-
1
-
-
-
-
-
2
-
-
2
-
-
-
-
-
-
-
-
2
-
-
65
-
-
-
2
1
-
-
65
71
-
-
-
-
-
1
-
-
-
-
-
2
-
-
2
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
739953
Endo
Characterization of rabbit mor ...
Oryctolagus cuniculus
Arch. Biochem. Biophys.
529
131-139
2013
-
-
1
-
4
-
10
85
-
-
-
2
-
4
-
-
1
-
-
8
-
-
120
-
1
-
-
84
3
-
-
3
6
-
34
-
-
3
7
-
4
-
36
30
6
88
-
-
-
2
-
-
-
2
-
12
-
-
120
-
3
-
-
86
8
-
-
-
-
3
6
-
-
-
723866
Jackson
Structure of AKR1C3 with 3-phe ...
Homo sapiens
Acta Crystallogr. Sect. F
68
409-413
2012
-
-
1
1
-
-
1
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
724533
Chen
Crystal structures of AKR1C3 c ...
Homo sapiens
Bioorg. Med. Chem. Lett.
22
3492-3497
2012
-
-
-
1
-
-
2
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
1
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
724538
Sinreih
N-Benzoyl anthranilic acid der ...
Homo sapiens
Bioorg. Med. Chem. Lett.
22
5948-5951
2012
-
-
-
-
-
-
4
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
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-
-
4
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
725153
Miller
Aldo-keto reductase family 1 m ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
5
278-289
2012
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
725671
Brozic
Selective inhibitors of aldo-k ...
Homo sapiens
J. Med. Chem.
55
7417-7424
2012
-
-
-
1
-
-
2
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
2
-
2
-
-
-
-
1
-
-
2
2
2
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
725825
Byrns
Overexpression of aldo-keto re ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
130
7-15
2012
-
-
-
-
-
-
-
-
-
-
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1
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2
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2
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-
-
-
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-
-
-
-
1
1
-
-
-
724517
Adeniji
Discovery of substituted 3-(ph ...
Homo sapiens
Bioorg. Med. Chem. Lett.
21
1464-1468
2011
-
-
-
-
-
-
3
-
-
-
-
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1
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1
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3
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-
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-
3
3
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-
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
711670
Guise
The bioreductive prodrug PR-10 ...
Homo sapiens
Cancer Res.
70
1573-1584
2010
-
1
-
-
-
-
-
-
-
-
-
-
-
2
-
-
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-
-
1
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1
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-
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-
-
-
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-
1
-
-
-
-
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-
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-
1
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
712882
Byrns
Aldo-keto reductase 1C3 expres ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
118
177-187
2010
-
1
1
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
1
-
-
4
-
-
-
-
1
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
1
-
1
-
-
4
-
-
-
-
1
-
-
-
-
-
-
-
-
1
1
713574
Ashley
Developmental evaluation of al ...
Homo sapiens
Urology
76
67-72
2010
-
1
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
725152
Zakharov
Suppressed expression of type ...
Homo sapiens
Int. J. Clin. Exp. Pathol.
3
608-617
2010
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
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1
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-
-
-
-
-
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-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
712571
Nakamura
Type 5 17ß-hydroxysteroid deh ...
Homo sapiens
J. Clin. Endocrinol. Metab.
94
2192-2198
2009
-
-
-
-
-
-
-
-
-
-
-
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2
-
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-
-
-
4
-
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-
-
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-
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-
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4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
688137
Azzarello
Tissue distribution of human A ...
Homo sapiens, Rattus norvegicus
J. Histochem. Cytochem.
56
853-861
2008
-
2
-
-
-
-
-
-
4
-
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2
-
-
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-
-
10
-
-
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-
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-
-
-
-
-
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-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
10
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
670259
Ngatcha
3beta-Alkyl-androsterones as i ...
Homo sapiens
Mol. Cell. Endocrinol.
248
225-232
2006
-
-
-
-
-
-
3
-
-
-
-
1
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
673341
Fung
Increased expression of type 2 ...
Homo sapiens
Endocr. Relat. Cancer
13
169-180
2006
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
4
-
-
-
-
-
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-
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287209
Krazeisen
Phytoestrogens inhibit human 1 ...
Homo sapiens
Mol. Cell. Endocrinol.
171
151-162
2001
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1
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9
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1
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3
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2
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5
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5
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1
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1
1
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9
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3
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5
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5
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287210
Stupans
Testosterone dehydrogenase act ...
Homo sapiens, Notamacropus eugenii, Phascolarctos cinereus, Rattus norvegicus
Comp. Biochem. Physiol. B
125
245-250
2000
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1
4
4
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4
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9
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4
7
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4
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4
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4
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1
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4
4
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4
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4
7
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4
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287211
Carre
Characterization and solubizat ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
46
265-267
1993
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2
1
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1
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1
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1
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2
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1
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1
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2
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2
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2
1
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1
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1
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1
2
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1
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1
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287212
Dumont
Expression of human 17beta-hyd ...
Homo sapiens
J. Steroid Biochem. Mol. Biol.
41
605-608
1992
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1
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1
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1
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7
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3
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1
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1
1
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1
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7
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3
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286355
Sawada
Kinetic and stereochemical cha ...
Mesocricetus auratus
J. Biochem.
109
770-775
1991
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4
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1
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1
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1
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1
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2
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2
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4
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1
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1
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286354
Ohmura
Demonstration of 3alpha(17beta ...
Mesocricetus auratus
Biochem. J.
266
583-589
1990
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11
13
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1
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1
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1
1
1
10
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1
12
1
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4
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4
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11
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13
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1
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1
1
1
10
-
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1
12
1
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287213
Itagaki
Purification and characterizat ...
Ilyonectria destructans
J. Biochem.
103
1039-1044
1988
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6
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2
1
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1
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1
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1
1
3
1
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1
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2
1
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1
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1
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6
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2
1
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1
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1
1
3
1
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1
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2
1
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287214
Payne
Isolation of novel microbiol 3 ...
Alcaligenes sp.
J. Biol. Chem.
260
13648-13655
1985
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6
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3
1
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1
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1
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1
1
13
1
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1
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2
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1
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1
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6
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3
1
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1
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1
1
13
1
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1
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2
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287215
Blomquist
Microsomal 17beta-hydroxystero ...
Cavia porcellus
J. Steroid Biochem.
8
193-198
1977
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-
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1
1
4
1
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1
1
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1
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1
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1
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1
1
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1
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1
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1
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1
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4
1
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1
1
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1
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1
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1
1
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287216
Markert
-
Enzyminduktion bei Streptomyce ...
Streptomyces exfoliatus
Hoppe-Seyler's Z. Physiol. Chem.
356
1843-1852
1975
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2
3
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1
1
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1
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1
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8
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1
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1
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1
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1
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2
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3
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1
1
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1
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8
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1
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1
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287217
Ghraf
11beta- und 17beta-Hydroxyster ...
Rattus norvegicus
Hoppe-Seyler's Z. Physiol. Chem.
354
299-305
1973
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1
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1
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1
1
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1
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1
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1
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1
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1
1
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1
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287218
Endahl
-
Separation of a triphosphopyri ...
Cavia porcellus
J. Biol. Chem.
235
2793-2796
1960
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8
1
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1
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1
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1
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1
1
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1
1
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1
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1
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8
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1
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1
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1
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1
1
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1
1
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287219
Villee
Some properties of the pyridin ...
Cavia porcellus
J. Biol. Chem.
235
3615-3619
1960
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1
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1
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1
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1
1
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1
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1
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1
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1
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1
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1
1
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1
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-
-
287220
Sweat
Preparation and characterizati ...
Bos taurus
J. Biol. Chem.
185
75-84
1950
-
-
-
-
-
-
-
1
-
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-
1
-
1
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1
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1
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1
1
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1
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1
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1
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1
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1
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1
1
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