Estriol sulfate

Chemical compound From Wikipedia, the free encyclopedia

Estriol sulfate

Estriol sulfate, or estriol 3-sulfate, is a conjugated metabolite of estriol that is present in high quantities during pregnancy. It is formed from estriol in the liver and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estriol. Estriol sulfate is the second most prevalent conjugated metabolite of estriol during pregnancy; 35 to 46% is estriol glucuronide and 15 to 22% is estriol 3-sulfate, while the double conjugate estriol sulfate glucuronide also occurs.[1][2] Estriol sulfate was a component, along with estriol glucuronide, of the early pharmaceutical estrogens Progynon and Emmenin.[3][4][5][1]

Quick Facts Names, Identifiers ...
Estriol sulfate
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Names
IUPAC name
16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate
Systematic IUPAC name
(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 hydrogen sulfate
Other names
Estriol 3-sulfate; Estra-1,3,5(10)-triene-3,16α,17β-triol 3-sulfate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C18H24O6S/c1-18-7-6-13-12-5-3-11(24-25(21,22)23)8-10(12)2-4-14(13)15(18)9-16(19)17(18)20/h3,5,8,13-17,19-20H,2,4,6-7,9H2,1H3,(H,21,22,23)/t13-,14-,15+,16-,17+,18+/m1/s1
    Key: ZORQMBLUMWNJEQ-ZXXIGWHRSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
Properties
C18H24O6S
Molar mass 368.44 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References

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