Chemistry:Estradiol 3-glucuronide
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| Names | |
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| IUPAC name
17β-Hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
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| Systematic IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(1S,3aS,3bR,9bS,11aS)-1-hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid | |
| Other names
E2-3G; 17β-Estradiol 3-(β-D-glucuronide)
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C24H32O8 | |
| 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). | |
| Infobox references | |
Estradiol 3-glucuronide (E2-3G), also known as 17β-estradiol 3-(β-D-glucuronide), is a naturally occurring and endogenous estrogen conjugate.[1] It is specifically the C3 glucuronide conjugate of estradiol, the major estrogen in the body.[1] It is formed from estradiol in the liver by UDP-glucuronosyltransferase via attachment of glucuronic acid and is eventually excreted in urine and bile.[2][3] Similarly to estrogen sulfates like estrone sulfate, estrogen glucuronides have much higher water solubility than do unconjugated estrogens like estradiol.[3]
Estrogen glucuronides can be deconjugated into the corresponding free estrogens by β-glucuronidase in tissues that express this enzyme, such as the mammary gland.[2] As a result, estrogen glucuronides have estrogenic activity via conversion into estrogens.[2]
Estradiol 3-glucuronide is a positional isomer of estradiol 17β-glucuronide.
See also
- Catechol estrogen
- Estradiol sulfate
- Estriol glucuronide
- Estriol sulfate
- Estrogen conjugate
- Lipoidal estradiol
References
- ↑ 1.0 1.1 "Human Metabolome Database: Showing metabocard for 17-beta-Estradiol-3-glucuronide (HMDB0006224)". http://www.hmdb.ca/metabolites/HMDB0006224.
- ↑ 2.0 2.1 2.2 "Functional role of estrogen metabolism in target cells: review and perspectives". Carcinogenesis 19 (1): 1–27. January 1998. doi:10.1093/carcin/19.1.1. PMID 9472688.
- ↑ 3.0 3.1 "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf.
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