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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
ChEBI
ChEMBL
UNII
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
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
C 21 H 36 O 2
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).
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]
Chemistry
References
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CAR Tooltip Constitutive androstane receptor
PXR Tooltip Pregnane X receptor