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Literature summary extracted from
- Determination of 17alpha-hydroxylase-C17,20-lyase (P45017alpha) enzyme activities and their inhibition by selected steroidal picolyl and picolinylidene compounds (2015), Acta Biol. Hung., 66, 41-51.
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.19 | 17(E)-picolinyliden-androst-4-en-3-one | complete inhibition at 0.05 mM | Rattus norvegicus |  |
| 1.14.14.19 | 17(E)-picolinyliden-androst-4-en-3beta-ol | 52% inhibition at 0.05 mM | Rattus norvegicus | |
| 1.14.14.19 | 17(E)-picolinyliden-androst-5-en-3beta-ol | 55% inhibition at 0.05 mM | Rattus norvegicus | |
| 1.14.14.19 | 17alpha-picolyl-androst-4-en-3beta,17beta-diol | 10% inhibition at 0.05 mM | Rattus norvegicus | |
| 1.14.14.19 | 17alpha-picolyl-androst-5-en-3beta,17beta-diol | 5% inhibition at 0.05 mM | Rattus norvegicus | |
| 1.14.14.19 | 17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one | 13% inhibition at 0.05 mM | Rattus norvegicus | |
| 1.14.14.19 | abiraterone | - |
Rattus norvegicus | |
| 1.14.14.32 | 17(E)-picolinyliden-androst-4-en-3beta-ol | - |
Rattus norvegicus | |
| 1.14.14.32 | 17(E)-picolinyliden-androst-5-en-3beta-ol | - |
Rattus norvegicus | |
| 1.14.14.32 | abiraterone | - |
Rattus norvegicus | |
| 1.14.14.32 | ketoconazole | - |
Rattus norvegicus | |
| 1.14.14.32 | additional information | picolyl derivatives exert no significant inhibition either on the 17alpha-hydroxylase or the C17,20-lyase activities | 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 | pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 | Rattus norvegicus | - |
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.19 | progesterone + [reduced NADPH-hemoprotein reductase] + O2 | Rattus norvegicus | - |
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Organic Solvent Stability
| EC Number | Organic Solvent | Comment | Organism |
|---|---|---|---|
| 1.14.14.32 | dimethyl sulfoxide | 5% v/v, no significant reduction of activity | Rattus norvegicus |
| 1.14.14.32 | propylene glycol | 3% v/v, no significant reduction of activity | Rattus norvegicus |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.19 | Rattus norvegicus | - |
- |
- |
| 1.14.14.32 | Rattus norvegicus | - |
- |
- |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.14.14.19 | testis | - |
Rattus norvegicus | - |
| 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 | pregnenolone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Rattus norvegicus | 17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.19 | progesterone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Rattus norvegicus | 17alpha-hydroxyprogesterone + [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 | - |
? | |
| 1.14.14.32 | 17alpha-picolyl-androst-4-en-3beta,17beta-diol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Rattus norvegicus | ? + acetate + [oxidized NADPH-hemoprotein reductase] + H2O | 66% conversion in 17,20-lyase reaction | ? | |
| 1.14.14.32 | 17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one + [reduced NADPH-hemoprotein reductase] + O2 | - |
Rattus norvegicus | ? + acetate + [oxidized NADPH-hemoprotein reductase] + H2O | 73% conversion in 17,20-lyase reaction | ? | |
| 1.14.14.32 | additional information | the enzyme catalyses two independent reactions at the same active site, the 17-hydroxylation of pregnenolone and progesterone (reaction of EC 1.14.14.19), and the conversion of the 17-hydroxylated products via a 17,20-lyase reaction. The C17,20-lyase reaction is rate limiting, and 525% of the 17OH-progesterone product is converted to 4-en-dione | Rattus norvegicus | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.19 | 17alpha-hydroxylase-C17,20-lyase | - |
Rattus norvegicus |
| 1.14.14.19 | P45017alpha | - |
Rattus norvegicus |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.19 | 0.0059 | - |
at pH 7.3 and 37°C | Rattus norvegicus | 17(E)-picolinyliden-androst-4-en-3-one | |
| 1.14.14.19 | 0.038 | - |
at pH 7.3 and 37°C | Rattus norvegicus | 17(E)-picolinyliden-androst-5-en-3beta-ol | |
| 1.14.14.19 | 0.048 | - |
at pH 7.3 and 37°C | Rattus norvegicus | 17(E)-picolinyliden-androst-4-en-3beta-ol | |
| 1.14.14.32 | 0.000012 | - |
C17,20-lyase activity, pH 7.3, 37°C | Rattus norvegicus | abiraterone | |
| 1.14.14.32 | 0.00032 | - |
C17,20-lyase activity, pH 7.3, 37°C | Rattus norvegicus | ketoconazole | |
| 1.14.14.32 | 0.0082 | - |
C17,20-lyase activity, pH 7.3, 37°C | Rattus norvegicus | 17(E)-picolinyliden-androst-5-en-3beta-ol | |
| 1.14.14.32 | 0.014 | - |
C17,20-lyase activity, pH 7.3, 37°C | Rattus norvegicus | 17(E)-picolinyliden-androst-4-en-3beta-ol | |
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