Estradiol 17β-sulfate

Estradiol 17β-sulfate is an estrogen conjugate which is produced from estradiol by sulfation of the C17β hydroxyl group by estrogen sulfotransferases.[1][2][3][4]

Estradiol 17β-sulfate
Names
Preferred IUPAC name
(1S,3aS,3bR,9bS,11aS)-7-Hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-1-yl hydrogen sulfate
Other names
Estra-1,3,5(10)-triene-3,17β-diol 17β-(hydrogen sulfate)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
InChI
  • InChI=1S/C18H24O5S/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)23-24(20,21)22/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,17+,18+/m1/s1
    Key: JSUDNGPWAXYETN-ZBRFXRBCSA-N
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OS(=O)(=O)O)CCC4=C3C=CC(=C4)O
Properties
Chemical formula
 C18H24O5S
Molar mass 352.45 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. Yoshizawa I, Takanashi K, Watanabe K, Sato T, Honjo H, Tanaka K, Sakuragi N, Fujimoto S (March 1992). "The physiological role of estradiol 17-sulfate during pregnancy". J. Steroid Biochem. Mol. Biol. 41 (3–8): 567–70. doi:10.1016/0960-0760(92)90385-v. PMID 1314078. S2CID 42879796.
  2. Honjo H (November 1992). "[Endogenous levels and dynamics of estrogen sulfates--physiological and pathological roles of estrone sulfate and estradiol 17-sulfate]". Nihon Naibunpi Gakkai Zasshi (in Japanese). 68 (11): 1158–66. doi:10.1507/endocrine1927.68.11_1158. PMID 1468592.
  3. Wang LQ, James MO (September 2005). "Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate". J. Steroid Biochem. Mol. Biol. 96 (5): 367–74. doi:10.1016/j.jsbmb.2005.05.002. PMID 16011896. S2CID 24671971.
  4. Brooks SC, Horn L (February 1971). "Hepatic sulfation of estrogen metabolites". Biochim. Biophys. Acta. 231 (1): 233–41. doi:10.1016/0005-2760(71)90272-4. PMID 4323008.


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