Estradiol 3-glucuronide

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Estradiol 3-glucuronide
Estradiol 3-glucuronide.svg
Names
IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
Other names
E2-3G; 17β-Estradiol 3-(β-D-glucuronide); 17β-Hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid;
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
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[edit]

References[edit]

  1. ^ a b http://www.hmdb.ca/metabolites/HMDB0006224
  2. ^ a b c 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.
  3. ^ a b 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.

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