Estrone glucuronide

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Column 1Column 2
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
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}2479-90-5
3D model (JSmol)Interactive image
ChEMBLChEMBL1232444
ChemSpider103124
KEGGC11133
PubChem CID115255
UNII933Q277TO2
CompTox Dashboard (EPA)DTXSID20891497
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/s1Key: FJAZVHYPASAQKM-JBAURARKSA-N
SMILES
C[C@]12CC[C@H]3C@HCCC4=C3C=CC(=C4)O[C@H]5C@@HO
Chemical formulaC24H30O8
Molar mass446.496 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. 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. It has much higher water solubility than does estrone. Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.

When exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver. A single administered dose of estradiol is absorbed 15% as estrone, 25% as estrone sulfate, 25% as estradiol glucuronide, and 25% as estrone glucuronide. 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. 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. In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the pharmacokinetics of estradiol, the terminal half-life of oral estradiol is 13 to 20 hours whereas with intravenous injection its terminal half-life is only about 1 to 2 hours.

EstrogenOther namesRBATooltip Relative binding affinity (%)aREP (%)b
EstradiolE2100100100
Estradiol 3-sulfateE2S; E2-3S?0.020.04
Estradiol 3-glucuronideE2-3G?0.020.09
Estradiol 17β-glucuronideE2-17G?0.0020.0002
Estradiol benzoateEB; Estradiol 3-benzoate101.10.52
Estradiol 17β-acetateE2-17A31–4524?
Estradiol diacetateEDA; Estradiol 3,17β-diacetate?0.79?
Estradiol propionateEP; Estradiol 17β-propionate19–262.6?
Estradiol valerateEV; Estradiol 17β-valerate2–110.04–21?
Estradiol cypionateEC; Estradiol 17β-cypionate?c4.0?
Estradiol palmitateEstradiol 17β-palmitate0??
Estradiol stearateEstradiol 17β-stearate0??
EstroneE1; 17-Ketoestradiol115.3–3814
Estrone sulfateE1S; Estrone 3-sulfate20.0040.002
Estrone glucuronideE1G; Estrone 3-glucuronide?<0.0010.0006
EthinylestradiolEE; 17α-Ethynylestradiol10017–150129
MestranolEE 3-methyl ether11.3–8.20.16
QuinestrolEE 3-cyclopentyl ether?0.37?
Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page.
Column 1
vte Metabolic pathways of estradiol in humans

Estradiol

Estrone sulfate

Estrone glucuronide

2-Hydroxyestrone

Estrone

4-Hydroxyestrone

2-Methoxyestrone

16α-Hydroxyestrone

4-Methoxyestrone

17-Epiestriol

Estriol

16-Epiestriol

17β-HSD EST STS UGT1A3UGT1A9

CYP450 CYP450

COMT CYP450 COMT

unidentified 17β-HSD unidentified

Description: The metabolic pathways involved in the metabolism of estradiol and other natural estrogens (e.g., estrone, estriol) in humans. In addition to the metabolic transformations shown in the diagram, conjugation (e.g., sulfation and glucuronidation) occurs in the case of estradiol and metabolites of estradiol that have one or more available hydroxyl (–OH) groups. Sources: See template page. |

  • Catechol estrogen
  • Estradiol sulfate
  • Estriol glucuronide
  • Estriol sulfate
  • Estrogen conjugate
  • Lipoidal estrogen

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  • Metabocard of Estrone Glucuronide – Human Metabolome Database