Pregnanediol glucuronide

Pregnanediol glucuronide, or 5β-pregnane-3α,20α-diol 3α-glucuronide, is the major metabolite of progesterone and the C3α glucuronide conjugate of pregnanediol (5β-pregnane-3α,20α-diol).[1][2] Approximately 15 to 30% of a parenteral dose of progesterone is metabolized into pregnanediol glucuronide.[1][2] While this specific isomer is referred to as pregnanediol glucuronide and is the most major form, there are actually many possible isomers of the metabolite.[3][4]

Pregnanediol glucuronide
Names
Preferred IUPAC name
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-({(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-1-[(1S)-1-hydroxyethyl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl}oxy)oxane-2-carboxylic acid
Other names
Pregnanediol 3α-glucuronide; 5β-Pregnane-3α,20α-diol 3α-glucuronide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
InChI
  • InChI=1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16-,17+,18-,19-,20-,21-,22+,23-,25+,26-,27+/m0/s1
    Key: ZFFFJLDTCLJDHL-JQYCEVDMSA-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@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C)C)O
Properties
Chemical formula
 C27H44O8
Molar mass 496.641 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Josimovich J (11 November 2013). Gynecologic Endocrinology. Springer Science & Business Media. p. 28. ISBN 978-1-4613-2157-6.
  2. Etienne-Emile Baulieu; Paul A. Kelly (30 November 1990). Hormones: From Molecules to Disease. Springer Science & Business Media. pp. 401–. ISBN 978-0-412-02791-8.
  3. Cupps PT (20 February 1991). Reproduction in Domestic Animals. Elsevier. pp. 101–. ISBN 978-0-08-057109-6.
  4. R. Hobkirk (18 January 2018). Steroid Biochemistry. CRC Press. pp. 23–. ISBN 978-1-351-09380-4.



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