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Literature summary extracted from

  • Ondre, D.; Woelfling, J.; Toth, I.; Szecsi, M.; Julesz, J.; Schneider, G.
    Steroselective synthesis of some steroidal oxazolines, as novel potential inhibitors of 17alpha-hydroxylase-C17,20-lyase (2009), Steroids, 74, 1025-1032.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.32 (17beta)-17-[(5R)-2-(2-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (17beta)-17-[(5R)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (17beta)-17-[(5R)-2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (17beta)-17-[(5R)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
-
 Rattus norvegicus
1.14.14.32 (3beta,17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
-
 Rattus norvegicus
1.14.14.32 (3beta,17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-fluorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
 Rattus norvegicus
1.14.14.32 (5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
 Rattus norvegicus
1.14.14.32 ketoconazole
-
 Rattus norvegicus
1.14.14.32 additional information no enzyme inhibition by (5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol and (5'R)-17beta-[2-(4-fluoroophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.32 Rattus norvegicus
-
 Wistar rats
-

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.
1.14.14.32 17-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
-
 Rattus norvegicus androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + 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
1.14.14.32 17alpha-hydroxylase-C17,20-lyase
-
 Rattus norvegicus
1.14.14.32 C17,20-lyase
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.14.32 37
-
 assay at Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.14.32 7.3
-
 assay at Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.32 NADPH
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.14.32 0.00035
-
-
 Rattus norvegicus ketoconazole
1.14.14.32 0.0048
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.0048
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
1.14.14.32 0.005
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.005
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
1.14.14.32 0.0077
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.0077
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
1.14.14.32 0.0079
-
 37°C Rattus norvegicus (3beta,17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
1.14.14.32 0.0079
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
1.14.14.32 0.011
-
 37°C Rattus norvegicus (3beta,17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
1.14.14.32 0.014
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-(2-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.014
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
1.14.14.32 0.03
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.03
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
1.14.14.32 0.052
-
 37°C Rattus norvegicus (17beta)-17-[(5R)-2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
1.14.14.32 0.052
-
 pH 7.3, 37°C Rattus norvegicus (5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one