Estriol sulfate glucuronide

Estriol sulfate glucuronide, or estriol 3-sulfate 16α-glucuronide, is an endogenous, naturally occurring diconjugated metabolite of estriol.[1] It is generated in the liver from estriol sulfate by UDP-glucuronyltransferase and is eventually excreted in the urine by the kidneys.[1] It occurs in high concentrations during pregnancy along with estriol sulfate and estriol glucuronide,[2] and was a component of the early pharmaceutical estrogens Progynon and Emmenin.[3][4][5][2]

Estriol sulfate glucuronide
Names
IUPAC name
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid
Other names
Estriol 3-sulfate 16α-glucuronide; 17β-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16α-yl-β-D-glucopyranosiduronic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C24H32O12S/c1-24-7-6-13-12-5-3-11(36-37(31,32)33)8-10(12)2-4-14(13)15(24)9-16(21(24)28)34-23-19(27)17(25)18(26)20(35-23)22(29)30/h3,5,8,13-21,23,25-28H,2,4,6-7,9H2,1H3,(H,29,30)(H,31,32,33)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23?,24+/m1/s1 (H,31,32,33)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23?,24+/m1/s1
    Key: ATNWFRGUDKUYOG-SUPAOECSSA-N
SMILES
  • [H][C@@]12C[C@@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OS(O)(=O)=O)C=C3
Properties
Chemical formula
 C24H32O12S
Molar mass 544.57 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. "Human Metabolome Database: Showing metabocard for Estriol 3-sulfate 16-glucuronide (HMDB0010356)".
  2. N. S. Assali (3 September 2013). The Maternal Organism. Elsevier. pp. 339–. ISBN 978-1-4832-6380-9.
  3. Thom Rooke (1 January 2012). The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5.
  4. Gregory Pincus (22 October 2013). Recent Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference. Elsevier Science. pp. 307–. ISBN 978-1-4832-1945-5.
  5. Robert K. Creasy; Robert Resnik; Charles J. Lockwood; Jay D. Iams; Michael F. Greene; Thomas Moore (2013). Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice. Elsevier Health Sciences. pp. 104–. ISBN 978-1-4557-1137-6.
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