Allopregnanediol (original) (raw)

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Allopregnanediol
Names
IUPAC name 5α-Pregnane-3α,20α-diol
Systematic IUPAC name (1_S_,3a_S_,3b_R_,5a_S_,7_R_,9a_S_,9b_S_,11a_S_)-1-[(1_S_)-1-Hydroxyethyl]-9a,11a-dimethylhexadecahydro-1_H_-cyclopenta[_a_]phenanthren-7-ol
Identifiers
CAS Number 566-58-5 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:8387
ChEMBL ChEMBL269897
ChemSpider 190585
EC Number 201-313-7
KEGG C05484D00189
PubChem CID 219833
UNII 97N2Q625GO checkY
CompTox Dashboard (EPA) DTXSID40859115 Edit this at Wikidata
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/s1Key: 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

Chemical compound

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]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.