Pregnenolone

Not to be confused with Pregnanolone or Pregneninolone.
This article is about pregnenolone as a hormone. For its use as a medication or supplement, see Pregnenolone (medication).
Pregnenolone
Names
IUPAC name
3β-Hydroxypregn-5-en-20-one
Systematic IUPAC name
1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
P5; 5-Pregnenolone; δ5-Pregnene-3β-ol-20-one; Pregn-5-en-3β-ol-20-one; NSC-1616
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.135 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
    Key: ORNBQBCIOKFOEO-QGVNFLHTSA-N
  • 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
Properties
C21H32O2
Molar mass 316.485 g/mol
Melting point 193 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.[2]

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.

  1. ^ Henderson E, Weinberg M, Wright WA (April 1950). "Pregnenolone". J. Clin. Endocrinol. Metab. 10 (4): 455–74. doi:10.1210/jcem-10-4-455. PMID 15415436.
  2. ^ Cite error: The named reference pmid21756978 was invoked but never defined (see the help page).