Allopregnanediol

Allopregnanediol
Names
	IUPAC name 5α-Pregnane-3α,20α-diol
	Systematic IUPAC name (1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-[(1S)-1-Hydroxyethyl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
CAS Number	566-58-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8387;
ChEMBL	ChEMBL269897;
ChemSpider	190585;
EC Number	201-313-7;
KEGG	C05484; D00189;
PubChem CID	219833;
UNII	97N2Q625GO ;
CompTox Dashboard (EPA)	DTXSID40859115 ;
	InChI InChI=1S/C21H36O2/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/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1 Key: YWYQTGBBEZQBGO-BERLURQNSA-N;
	SMILES C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C)O;
Properties
Chemical formula	C21H36O2
Molar mass	320.517 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Allopregnanediol, or 5α-pregnane-3α,20α-diol, is an endogenous metabolite of progesterone and allopregnanolone and an isomer of pregnanediol (5β-pregnan-3α,20α-diol).^[1] It has been found to act like a partial agonist of an allosteric site of the GABA receptor and hence might play a biological role as a neurosteroid.^[2] It has also been found to act as an agonist of the human pregnane X receptor, albeit with an EC₅₀ that is more than an order of magnitude lower than that of other endogenous pregnanes like pregnenolone, pregnanediol, allopregnanedione, and allopregnanolone.^[3]

Chemistry

^ Finn, Deborah A.; Purdy, Robert H. (2007). "Neuroactive Steroids in Anxiety and Stress". Handbook of Contemporary Neuropharmacology. doi:10.1002/9780470101001.hcn026. ISBN 978-0470101001.
^ Belelli D, Gee KW (1989). "5 alpha-pregnan-3 alpha,20 alpha-diol behaves like a partial agonist in the modulation of GABA-stimulated chloride ion uptake by synaptoneurosomes". Eur. J. Pharmacol. 167 (1): 173–6. doi:10.1016/0014-2999(89)90760-7. PMID 2550257.
^ Ekins, Sean; Reschly, Erica J; Hagey, Lee R; Krasowski, Matthew D (2008). "Evolution of pharmacologic specificity in the pregnane X receptor". BMC Evolutionary Biology. 8 (1): 103. Bibcode:2008BMCEE...8..103E. doi:10.1186/1471-2148-8-103. ISSN 1471-2148. PMC 2358886. PMID 18384689.

This article about a steroid is a stub. You can help Wikipedia by expanding it.