Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:14:25 UTC
Update Date2024-04-30 20:32:12 UTC
Metabolite IDMMDBc0047908
Metabolite Identification
Common Name17a-Hydroxypregnenolone
Description17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809 ).
Structure
Synonyms
ValueSource
(3beta)-3,17-Dihydroxypregn-5-en-20-oneChEBI
17-HydroxypregnenoloneChEBI
5-Pregnen-3beta,17alpha-diol-20-oneChEBI
(3b)-3,17-Dihydroxypregn-5-en-20-oneGenerator
(3Β)-3,17-dihydroxypregn-5-en-20-oneGenerator
5-Pregnen-3b,17a-diol-20-oneGenerator
5-Pregnen-3β,17α-diol-20-oneGenerator
17-Hydroxy-D5-pregnenoloneHMDB
17-OH-PregnenoloneHMDB
17a-HydroxypregnoloneHMDB
17alpha-HydroxypregnanoloneHMDB
17alpha-HydroxypregnenoloneHMDB
3b,17-Dihydroxy-5-pregnen-20-oneHMDB
3b,17-Dihydroxy-pregn-5-en-20-oneHMDB
3b,17a-Dihydroxypregn-5-en-20-oneHMDB
17alpha HydroxypregnenoloneHMDB
HydroxypregnenoloneHMDB
17 HydroxypregnenoloneHMDB
17 alpha HydroxypregnenoloneHMDB
17-Hydroxypregnenolone, (3alpha)-isomerHMDB
17-Hydroxypregnenolone, (3beta,13alpha)-isomerHMDB
17-alpha-HydroxypregnenoloneHMDB
17 alpha-HydroxypregnenoloneHMDB
17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomerHMDB
17-Hydroxypregnenolone, (3beta,17alpha)-isomerHMDB
Molecular FormulaC21H32O3
Average Mass332.477
Monoisotopic Mass332.23514489
IUPAC Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry Number387-79-1
SMILES
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1
InChI KeyJERGUCIJOXJXHF-TVWVXWENSA-N