Structure via PubChem · Public domain (PubChem)
17α-hydroxypregnenolone
Sign in to saveAlso known as (3β)-3,17-dihydroxypregn-5-en-20-one, 17-hydroxypregnenolone, 17alpha-Hydroxypregnenolone, 5-pregnen-3β,17α-diol-20-one, 17-alpha-OH-Pregnenolone
17α-Hydroxypregnenolone is a pregnane (C21) steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline. High levels are also achieved during pregnancy. It is also a known neuromodulator.
Chemical data
- Formula
- C21H32O3
- Molecular weight
- 332.5 g/mol
- IUPAC name
- 1-[(3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
- SMILES
- CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O
- InChIKey
- JERGUCIJOXJXHF-TVWVXWENSA-N
- XLogP
- 3.1
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
823 papers- [17alpha-hydroxypregnenolone].Nihon rinsho. Japanese journal of clinical medicine · 2005
- [17 alpha-hydroxypregnenolone].Nihon rinsho. Japanese journal of clinical medicine · 1995
- [17alpha-Hydroxypregnenolone].Nihon rinsho. Japanese journal of clinical medicine · 2010
- 7α-Hydroxypregnenolone, a new key regulator of amphibian locomotion: discovery, progress and prospect.General and comparative endocrinology · 2012
- [17 alpha-Hydroxypregnenolone].Nihon rinsho. Japanese journal of clinical medicine · 1999
via PubMed
Wikidata facts
- Mass
- 332.23514488399996
Show 6 more facts
- subject has role
- primary metabolite
- canonical SMILES
- CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
- isomeric SMILES
- CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O
- chemical formula
- C₂₁H₃₂O₃
- found in taxon
- Homo sapiens
- Commons category
- 17-Hydroxypregnenolone
via Wikidata · CC0
~2 min read
Encyclopedic overview
6 sectionsContents
- Prohormone
- Clinical use
- Neurosteroid
- See also
- Additional images
- References
17α-Hydroxypregnenolone is a pregnane (C21) steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline. High levels are also achieved during pregnancy. It is also a known neuromodulator.
==Prohormone== 17α-Hydroxypregnenolone is considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohormone of the sex steroids.
Excerpted from Wikipedia’s “17α-hydroxypregnenolone” article, available under the CC BY-SA 4.0 licence.