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Literature summary extracted from

  • Ahmed, S.; Shahid, I.; Dhanani, S.; Owen, C.P.
    Synthesis and biochemical evaluation of a range of sulfonated derivatives of 4-hydroxybenzyl imidazole as highly potent inhibitors of rat testicular 17alpha-hydroxylase/17,20-lyase (P-450(17alpha)) (2009), Bioorg. Med. Chem. Lett., 19, 4698-4701.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.19 1-(4-chlorobenzyl)-1H-imidazole
-
 Homo sapiens
1.14.14.19 1-(4-fluorobenzyl)-1H-imidazole
-
 Homo sapiens
1.14.14.19 1-(4-methylbenzyl)-1H-imidazole
-
 Homo sapiens
1.14.14.19 1-(4-nitrobenzyl)-1H-imidazole
-
 Homo sapiens
1.14.14.19 1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-methylbenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
-
 Homo sapiens
1.14.14.19 4-(1H-imidazol-1-ylmethyl)phenyl benzenesulfonate
-
 Homo sapiens
1.14.14.19 4-hydroxybenzyl imidazole
-
 Homo sapiens
1.14.14.19 abiraterone
-
 Homo sapiens
1.14.14.19 ketoconazole
-
 Homo sapiens
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-(1H-imidazol-1-ylmethylphenyl)-4-toluenesulfonate
-
 Rattus norvegicus
1.14.14.32 4-iodobenzyl imidazole
-
 Rattus norvegicus
1.14.14.32 ketoconazole
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.32 microsome
-
 Rattus norvegicus
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.19 progesterone + 2 NADPH + 2 H+ + 2 O2 Homo sapiens reaction via 17alpha-hydroxyprogesterone androstenedione + acetate + 2 NADP+ + 2 H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.19 Homo sapiens
-
-
-
1.14.14.32 Rattus norvegicus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.32 testis
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.19 progesterone + 2 NADPH + 2 H+ + 2 O2 reaction via 17alpha-hydroxyprogesterone Homo sapiens androstenedione + acetate + 2 NADP+ + 2 H2O
-
 ?
1.14.14.32 17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
-
 Rattus norvegicus androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.19 17alpha-hydroxylase
-
 Homo sapiens
1.14.14.19 17alpha-hydroxylase/17,20-lyase
-
 Homo sapiens
1.14.14.19 17alpha-OHase
-
 Homo sapiens
1.14.14.19 P450-17alpha
-
 Homo sapiens
1.14.14.32 17,20 lyase
-
 Rattus norvegicus
1.14.14.32 17alpha-hydroxylase/17,20-lyase
-
 Rattus norvegicus
1.14.14.32 P-45017alpha
-
 Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.19 NADPH
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.14.32 0.0000651
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
1.14.14.32 0.0000704
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
1.14.14.32 0.000085
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
1.14.14.32 0.0000987
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
1.14.14.32 0.0001009
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
1.14.14.32 0.00021
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
1.14.14.32 0.00023
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethylphenyl)-4-toluenesulfonate
1.14.14.32 0.0002908
-
 at 37°C Rattus norvegicus 4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
1.14.14.32 0.00158
-
 at 37°C Rattus norvegicus 4-iodobenzyl imidazole
1.14.14.32 0.00166
-
 at 37°C Rattus norvegicus ketoconazole