Chemistry:Estrone glucuronide

Estrone glucuronide
Names
	IUPAC name 17-Oxoestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
	Systematic IUPAC name (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(3aS,3bR,9bS,11aS)-11a-methyl-1-oxo-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid
	Other names Estrone 3-glucuronide; Estrone 3-D-glucuronide; Estra-1,3,5(10)-triene-3-ol-17-one 3-D-glucuronoside
Identifiers
CAS Number	2479-90-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1232444;
ChemSpider	103124;
KEGG	C11133;
PubChem CID	115255;
UNII	933Q277TO2;
	InChI InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1 Key: FJAZVHYPASAQKM-JBAURARKSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O;
Properties
Chemical formula	C24H30O8
Molar mass	446.496 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

Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone.^[1] It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys.^[1] It has much higher water solubility than does estrone.^[1] Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.^[1]

When exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver.^[2]^[3] A single administered dose of estradiol is absorbed 15% as estrone, 25% as estrone sulfate, 25% as estradiol glucuronide, and 25% as estrone glucuronide.^[2] Formation of estrogen glucuronide conjugates is particularly important with oral estradiol as the percentage of estrogen glucuronide conjugates in circulation is much higher with oral ingestion than with parenteral estradiol.^[2] Estrone glucuronide can be reconverted back into estradiol, and a large circulating pool of estrogen glucuronide and sulfate conjugates serves as a long-lasting reservoir of estradiol that effectively extends its terminal half-life of oral estradiol.^[2]^[3] In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the pharmacokinetics of estradiol,^[2] the terminal half-life of oral estradiol is 13 to 20 hours^[4] whereas with intravenous injection its terminal half-life is only about 1 to 2 hours.^[5]