E2-3G; 17β-Estradiol 3-(β-D-glucuronide); 17β-Hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid;
3D model (JSmol)
|Molar mass||448.512 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Estradiol 3-glucuronide (E2-3G), also known as 17β-estradiol 3-(β-D-glucuronide), is a naturally occurring and endogenous estrogen conjugate. It is specifically the C3 glucuronide conjugate of estradiol, the major estrogen in the body. It is formed from estradiol in the liver by UDP-glucuronosyltransferase via attachment of glucuronic acid and is eventually excreted in urine and bile. Similarly to estrogen sulfates like estrone sulfate, estrogen glucuronides have much higher water solubility than do unconjugated estrogens like estradiol.
Estrogen glucuronides can be deconjugated into the corresponding free estrogens by β-glucuronidase in tissues that express this enzyme, such as the mammary gland. As a result, estrogen glucuronides have estrogenic activity via conversion into estrogens.
- Catechol estrogen
- Estradiol sulfate
- Estriol glucuronide
- Estriol sulfate
- Estrogen conjugate
- Lipoidal estradiol
- Zhu BT, Conney AH (January 1998). "Functional role of estrogen metabolism in target cells: review and perspectives". Carcinogenesis. 19 (1): 1–27. doi:10.1093/carcin/19.1.1. PMID 9472688.
- Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.