Estriol 3-glucuronide

Estriol 3-glucuronide, or oestriol 3-glucuronide, also known as estriol 3-β-D-glucosiduronic acid, is a natural, steroidal estrogen and a glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol.[1] It is found in the urine of women as a reversibly formed metabolite of estriol.[2][3] The positional isomer of estriol 3-glucuronide, estriol 16α-glucuronide, also occurs as an endogenous metabolite of estriol, but to a much greater extent in comparison.[2][3]

Estriol 3-glucuronide
Names
IUPAC name
16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-6-{[(1R,2R,3aS,3bR,9bS,11aS)-1,2-Dihydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names
(16α,17β)-16,17-Dihydroxyestra-1(10),2,4-trien-3-yl β-D-glucopyranosiduronic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(32-23-19(28)17(26)18(27)20(33-23)22(30)31)8-10(12)2-4-14(13)15(24)9-16(25)21(24)29/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1
    Key: UZKIAJMSMKLBQE-JRSYHJKYSA-N
  • InChI=1/C24H32O9/c1-24-7-6-13-12-5-3-11(32-23-19(28)17(26)18(27)20(33-23)22(30)31)8-10(12)2-4-14(13)15(24)9-16(25)21(24)29/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1
    Key: UZKIAJMSMKLBQE-JRSYHJKYBO
  • C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H]([C@@H]2O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
Properties
C24H32O9
Molar mass 464.511 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

See also

References
  1. R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 274–. ISBN 978-0-412-27060-4.
  2. Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 265–. ISBN 978-3-642-60107-1.
  3. Musey, Paul I.; Kirdani, Rashad Y.; Bhanalaph, Thongchai; Sandberg, Avery A. (1973). "Estriol metabolism in the baboon: Analysis of urinary and biliary metabolites". Steroids. 22 (6): 795–817. doi:10.1016/0039-128X(73)90054-8. ISSN 0039-128X. PMID 4203562.


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