Chemistry:Etiocholanolone glucuronide
From HandWiki
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| Names | |
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| IUPAC name
17-Oxo-5β-androstan-3α-yl β-D-glucopyranosiduronic acid
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| Systematic IUPAC name
(2S,3S,4S,5R,6R)-6-{[(3aS,3bR,5aR,7R,9aS,9bS,11aS)-9a,11a-Dimethyl-1-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid | |
| Other names
5β-Androstan-3α-ol-17-one 3-glucuronide; 3α-Hydroxy-5β-androstan-17-one 3-glucuronide; Etiocholan-3α-ol-17-one 3-glucuronide; 3α-Hydroxyetiocholan-17-one 3-glucuronide; 17-oxoetiocholan-3α-yl β-D-glucopyranosiduronic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C25H38O8 | |
| Molar mass | 466.571 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
Etiocholanolone glucuronide (ETIO-G) is an endogenous, naturally occurring metabolite of testosterone.[1][2] It is formed in the liver from etiocholanolone by UDP-glucuronyltransferases.[3] ETIO-G has much higher water solubility than etiocholanolone and is eventually excreted in the urine via the kidneys.[1][2] Along with androsterone glucuronide, it is one of the major inactive metabolites of testosterone.[4][5]
Formation
A glucuronosyltransferase anzyme converts etiocholanolone to its glucuronide by adding a sugar acid to its hydroxy group, with uridine diphosphate (UDP) as byproduct:[3]
- REDIRECT Template:Chemical reaction
See also
- 3α,5β-Androstanediol
- 5β-Dihydrotestosterone
- Androstanediol glucuronide
References
- ↑ 1.0 1.1 "Human Metabolome Database: Showing metabocard for Etiocholanolone glucuronide (HMDB0004484)". Hmdb.ca. http://www.hmdb.ca/metabolites/HMDB04484. Retrieved 2022-04-15.
- ↑ 2.0 2.1 S. Bernstein; S. Solomon (6 December 2012). Chemical and Biological Aspects of Steroid Conjugation. Springer Science & Business Media. pp. 328–. ISBN 978-3-642-95177-0. https://books.google.com/books?id=Q1voCAAAQBAJ&pg=PA328.
- ↑ 3.0 3.1 Järvinen, Erkka; Kidron, Heidi; Finel, Moshe (2020). "Human efflux transport of testosterone, epitestosterone and other androgen glucuronides". The Journal of Steroid Biochemistry and Molecular Biology 197. doi:10.1016/j.jsbmb.2019.105518. PMID 31704245.
- ↑ David A. Williams; William O. Foye; Thomas L. Lemke (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 707–. ISBN 978-0-683-30737-5. https://books.google.com/books?id=qLJ6Bs1Qml4C&pg=PA707.
- ↑ Christina Wang (28 May 2007). Male Reproductive Function. Springer Science & Business Media. pp. 69–. ISBN 978-0-585-38145-9. https://books.google.com/books?id=mMp9BwAAQBAJ&pg=PA69.
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