Structure via PubChem · Public domain (PubChem)
pregnenolone
Sign in to saveAlso known as (3b)-3-hydroxy-Pregn-5-en-20-one, 3-Hydroxypregn-5-en-20-one, 5-Pregnen-3b-ol-20-one, Pregneton, Pregn-5-ene-3b-ol-20-one, Regnosone, Skinostelon, 3b-Hydroxypregn-5-en-20-one
Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.
Chemical data
- Formula
- C21H32O2
- Molecular weight
- 316.5 g/mol
- IUPAC name
- 1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
- SMILES
- CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- InChIKey
- ORNBQBCIOKFOEO-QGVNFLHTSA-N
- XLogP
- 4.2
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
8,092 papers- Pregnenolone promotes immune evasion through blocking endogenous retrovirus expression.Cell metabolism · 2026
- [Pregnenolone].Nihon rinsho. Japanese journal of clinical medicine · 1995
- Pregnenolone Reduces L-Dopa-Induced Dyskinesias in Female Parkinsonian Monkeys.Movement disorders : official journal of the Movement Disorder Society · 2025
- [Pregnenolone, pregnenolone sulfate].Nihon rinsho. Japanese journal of clinical medicine · 2005
- [Pregnenolone, pregnenolone sulfate].Nihon rinsho. Japanese journal of clinical medicine · 1999
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 316.24
- Has use
- medication
Show 6 more facts
- found in taxon
- Levisticum officinale
- chemical formula
- C₂₁H₃₂O₂
- isomeric SMILES
- CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- canonical SMILES
- CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
- Commons category
- Pregnenolone
- subject has role
- primary metabolite
via Wikidata · CC0
~7 min read
Encyclopedic overview
12 sectionsContents
- Biological function
- Biological activity
- Neurosteroid activity
- Nuclear receptor activity
- Biochemistry
- Biosynthesis
- Distribution
- Metabolism
- Levels
- Chemistry
- History
- References
Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.
In addition to its role as a natural hormone, pregnenolone has been used as a medication and supplement; for information on pregnenolone as a medication or supplement, see the pregnenolone (medication) article.
Excerpted from Wikipedia’s “pregnenolone” article, available under the CC BY-SA 4.0 licence.