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Literature summary extracted from

  • Shahid, I.; Patel, C.H.; Dhanani, S.; Owen, C.P.; Ahmed, S.
    Synthesis, biochemical evaluation of a range of potent 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17alpha-Hydroxylase/17,20-Lyase (P45017alpha) (2008), J. Steroid Biochem. Mol. Biol., 110, 18-29.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.32 1-(3-phenylpropyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-(4-bromobenzyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-(4-iodo-benzyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-(4-phenylbutyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-(5-phenylpentyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-(7-phenyl-heptyl)-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[3-(4-bromo-phenyl)-propyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[3-(4-chlorophenyl)-propyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[3-(4-fluorophenyl)-propyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[5-(4-bromo-phenyl)-pentyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
-
 Rattus norvegicus
1.14.14.32 1-[7-(4-fluorophenyl)-heptyl]-1H-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.
1.14.14.32 17alpha-Hydroxypregnenolone Rattus norvegicus 17,20-lyase activity Dehydroepiandrosterone + acetaldehyde
-
 ?
1.14.14.32 17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2 Rattus norvegicus 17,20-lyase activity androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.32 Rattus norvegicus
-
 Sprague-Dawley rat
-

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 17alpha-Hydroxypregnenolone 17,20-lyase activity Rattus norvegicus Dehydroepiandrosterone + acetaldehyde
-
 ?
1.14.14.32 17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2 17,20-lyase activity Rattus norvegicus androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.32 17alpha-hydroxylase/17,20-lyase
-
 Rattus norvegicus
1.14.14.32 P45017alpha
-
 Rattus norvegicus

Temperature Optimum [°C]

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

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.14.32 7.4
-
 activity assay Rattus norvegicus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.14.32 0.0000215
-
 1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole lyase IC50 value Rattus norvegicus
1.14.14.32 0.00004
-
 1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole lyase IC50 value Rattus norvegicus
1.14.14.32 0.000052
-
 1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole lyase IC50 value Rattus norvegicus
1.14.14.32 0.0000553
-
 1-(7-phenyl-heptyl)-1H-imidazole lyase IC50 value Rattus norvegicus
1.14.14.32 0.0000775
-
 1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole 17alpha-OHase IC50 value Rattus norvegicus
1.14.14.32 0.000207
-
 1-(7-phenyl-heptyl)-1H-imidazole 17alpha-OHase IC50 value Rattus norvegicus
1.14.14.32 0.000208
-
 1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole 17alpha-OHase IC50 value Rattus norvegicus
1.14.14.32 0.000265
-
 1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole 17alpha-OHase IC50 value Rattus norvegicus
1.14.14.32 0.000665
-
 ketoconazole
-
 Rattus norvegicus
1.14.14.32 0.00124
-
 ketoconazole
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.14.32 0.000057
-
 lyase IC50 value Rattus norvegicus 1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole
1.14.14.32 0.000058
-
 lyase IC50 value Rattus norvegicus 1-[5-(4-bromo-phenyl)-pentyl]-1H-imidazole
1.14.14.32 0.000086
-
 lyase IC50 value Rattus norvegicus 1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
1.14.14.32 0.0001
-
 lyase IC50 value Rattus norvegicus 1-(7-phenyl-heptyl)-1H-imidazole
1.14.14.32 0.0001
-
 lyase IC50 value Rattus norvegicus 1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
1.14.14.32 0.00017
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole
1.14.14.32 0.00032
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(7-phenyl-heptyl)-1H-imidazole
1.14.14.32 0.00033
-
 lyase IC50 value Rattus norvegicus 1-[3-(4-bromo-phenyl)-propyl]-1H-imidazole
1.14.14.32 0.0005
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[5-(4-bromo-phenyl)-pentyl]-1H-imidazole
1.14.14.32 0.00055
-
 lyase IC50 value Rattus norvegicus 1-[3-(4-chlorophenyl)-propyl]-1H-imidazole
1.14.14.32 0.00057
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
1.14.14.32 0.00075
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
1.14.14.32 0.00131
-
 lyase IC50 value Rattus norvegicus 1-(5-phenylpentyl)-1H-imidazole
1.14.14.32 0.00158
-
 lyase IC50 value Rattus norvegicus 1-(4-iodo-benzyl)-1H-imidazole
1.14.14.32 0.00166
-
-
 Rattus norvegicus ketoconazole
1.14.14.32 0.00196
-
 lyase IC50 value Rattus norvegicus 1-[3-(4-fluorophenyl)-propyl]-1H-imidazole
1.14.14.32 0.0022
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(5-phenylpentyl)-1H-imidazole
1.14.14.32 0.00223
-
 lyase IC50 value Rattus norvegicus 1-(4-phenylbutyl)-1H-imidazole
1.14.14.32 0.00285
-
 lyase IC50 value Rattus norvegicus 1-(4-bromobenzyl)-1H-imidazole
1.14.14.32 0.00295
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[3-(4-bromo-phenyl)-propyl]-1H-imidazole
1.14.14.32 0.00376
-
-
 Rattus norvegicus ketoconazole
1.14.14.32 0.00585
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[3-(4-chlorophenyl)-propyl]-1H-imidazole
1.14.14.32 0.00614
-
 lyase IC50 value Rattus norvegicus 1-(3-phenylpropyl)-1H-imidazole
1.14.14.32 0.00865
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(4-phenylbutyl)-1H-imidazole
1.14.14.32 0.01006
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(4-iodo-benzyl)-1H-imidazole
1.14.14.32 0.01655
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(4-bromobenzyl)-1H-imidazole
1.14.14.32 0.02781
-
 17alpha-OHase IC50 value Rattus norvegicus 1-[3-(4-fluorophenyl)-propyl]-1H-imidazole
1.14.14.32 0.03095
-
 17alpha-OHase IC50 value Rattus norvegicus 1-(3-phenylpropyl)-1H-imidazole