Chemistry:Estriol sulfate glucuronide
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| 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
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| Other names
Estriol 3-sulfate 16α-glucuronide; 17β-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16α-yl-β-D-glucopyranosiduronic acid
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3D model (JSmol)
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| Properties | |
| 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). | |
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Tracking categories (test):
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]
Formation
In the human liver, a glucuronosyltransferase anzyme converts estriol sulfate to its glucuronide by adding a sugar acid at one of the hydroxy groups, with uridine diphosphate (UDP) as byproduct:[1][6][7]
- REDIRECT Template:Chemical reaction
See also
- Catechol estrogen
- Estrogen conjugate
- Lipoidal estrogen
References
- ↑ 1.0 1.1 1.2 "Human Metabolome Database: Showing metabocard for Estriol 3-sulfate 16-glucuronide (HMDB0010356)". http://www.hmdb.ca/metabolites/HMDB10356.
- ↑ 2.0 2.1 N. S. Assali (3 September 2013). The Maternal Organism. Elsevier. pp. 339–. ISBN 978-1-4832-6380-9. https://books.google.com/books?id=mSzLBAAAQBAJ&pg=PA339.
- ↑ Thom Rooke (1 January 2012). The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5. https://books.google.com/books?id=70vvFrtpePoC&pg=PT54.
- ↑ 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. https://books.google.com/books?id=jgTgBAAAQBAJ&pg=PA307.
- ↑ 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. https://books.google.com/books?id=AbMKAQAAQBAJ&pg=PA104.
- ↑ 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.
- ↑ Oettel, Michael; Schillinger, Ekkehard (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. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA265.
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