Etiocholanolone glucuronide

Etiocholanolone glucuronide
Names
	IUPAC name 17-Oxo-5β-androstan-3α-yl β-D-glucopyranosiduronic acid
	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
Identifiers
CAS Number	3602-09-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37451;
ChemSpider	391377;
KEGG	C11136;
PubChem CID	443078;
UNII	9LK4DML9R2 ;
CompTox Dashboard (EPA)	DTXSID201335941 ;
	InChI InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14+,15+,16+,18+,19+,20-,21+,23-,24+,25+/m1/s1 Key: VFUIRAVTUVCQTF-SDHZCXLISA-N;
	SMILES C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O;
Properties
Chemical formula	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

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]

1 2 "Human Metabolome Database: Showing metabocard for Etiocholanolone glucuronide (HMDB0004484)". Hmdb.ca. Retrieved 2022-04-15.
1 2 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.
1 2 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 105518. doi:10.1016/j.jsbmb.2019.105518. hdl:10138/321153. 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.
↑ Christina Wang (28 May 2007). Male Reproductive Function. Springer Science & Business Media. pp. 69–. ISBN 978-0-585-38145-9.