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{{Chembox

| ImageFile = Estradiol 3-glucuronide.svg
| ImageSize = 250px
| ImageAlt =

| IUPACName = 17β-Hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
| SystematicName = (2''S'',3''S'',4''S'',5''R'',6''S'')-3,4,5-Trihydroxy-6-<nowiki/>{[(1''S'',3a''S'',3b''R'',9b''S'',11a''S'')-1-hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1''H''-cyclopenta[''a'']phenanthren-7-yl]oxy}oxane-2-carboxylic acid
| OtherNames = E2-3G; 17β-Estradiol 3-(β-D-glucuronide)

| Section1 = {{Chembox Identifiers
| CASNo = 15270-30-1
| ChEBI = 36489
| ChEMBL = 2074591
| ChemSpiderID = 389587
| InChI = 1S/C24H32O8/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/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1
| InChIKey = MUOHJTRCBBDUOW-QXYWQCSFSA-N
| KEGG = C05503
| PubChem = 440713
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
}}
| Section2 = {{Chembox Properties
| C=24 | H=32 | O=8
| MolarMass = 448.512 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Estradiol 3-glucuronide''' ('''E2-3G'''), also known as '''17β-estradiol 3-(β-D-glucuronide)''', is a [[naturally occurring]] and [[endogenous]] [[estrogen conjugate]].<ref name="HMDB">{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0006224|title=Human Metabolome Database: Showing metabocard for 17-beta-Estradiol-3-glucuronide (HMDB0006224)}}</ref> It is specifically the C3 [[glucuronide]] [[conjugation (biochemistry)|conjugate]] of [[estradiol]], the major [[estrogen]] in the body.<ref name="HMDB" /> It is formed from estradiol in the [[liver]] by [[UDP-glucuronosyltransferase]] via attachment of glucuronic acid and is eventually [[excretion|excreted]] in [[urine]] and [[bile]].<ref name="pmid9472688" /><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | pages = 3–63 | year = 2005 | issue = Suppl 1 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}}</ref> Similarly to estrogen [[sulfate]]s like [[estrone sulfate]], estrogen glucuronides have much higher [[water solubility]] than do unconjugated estrogens like estradiol.<ref name="pmid16112947" />

Estrogen glucuronides can be deconjugated into the corresponding free estrogens by [[β-glucuronidase]] in [[tissue (biology)|tissue]]s that express this [[enzyme]], such as the [[mammary gland]].<ref name="pmid9472688">{{cite journal | vauthors = Zhu BT, Conney AH | title = Functional role of estrogen metabolism in target cells: review and perspectives | journal = Carcinogenesis | volume = 19 | issue = 1 | pages = 1–27 | date = January 1998 | pmid = 9472688 | doi = 10.1093/carcin/19.1.1 | doi-access = free }}</ref> As a result, estrogen glucuronides have estrogenic activity via conversion into estrogens.<ref name="pmid9472688" />

Estradiol 3-glucuronide is a [[positional isomer]] of [[estradiol 17β-glucuronide]].

{{Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors}}

==See also==
* [[Catechol estrogen]]
* [[Estradiol sulfate]]
* [[Estriol glucuronide]]
* [[Estriol sulfate]]
* [[Estrogen conjugate]]
* [[Lipoidal estradiol]]

==References==
{{Reflist}}

==External links==
* [http://www.hmdb.ca/metabolites/HMDB0006224 Metabocard for 3-Estradiol Glucuronide - Human Metabolome Database]

{{Steroid hormones}}
{{Estrogen receptor modulators}}

[[Category:Estradiol esters]]
[[Category:Estrogens]]
[[Category:Glucuronide esters]]
[[Category:Human metabolites]]

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