Estrone glucuronide

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Estrone glucuronide
Names
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
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
KEGG
UNII
  • 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/s1
    Key: FJAZVHYPASAQKM-JBAURARKSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
Properties
C24H30O8
Molar mass 446.496 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Estrone glucuronide, or estrone-3-D-glucuronide, is a

water solubility than does estrone.[1] Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.[1]

When

intravenous injection its terminal half-life is only about 1 to 2 hours.[5]

Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
Estrogen Other names
RBA
Tooltip Relative binding affinity (%)a 		REP (%)b
ER
ERα
ERβ
Estradiol E2 100 100 100
Estradiol 3-sulfate
 E2S; E2-3S ? 0.02 0.04
Estradiol 3-glucuronide E2-3G ? 0.02 0.09
Estradiol 17β-glucuronide
 E2-17G ? 0.002 0.0002
Estradiol benzoate EB; Estradiol 3-benzoate 10 1.1 0.52
Estradiol 17β-acetate E2-17A 31–45 24 ?
Estradiol diacetate EDA; Estradiol 3,17β-diacetate ? 0.79 ?
Estradiol propionate
 EP; Estradiol 17β-propionate 19–26 2.6 ?
Estradiol valerate EV; Estradiol 17β-valerate 2–11 0.04–21 ?
Estradiol cypionate EC; Estradiol 17β-cypionate ?c 4.0 ?
Estradiol palmitate Estradiol 17β-palmitate 0 ? ?
Estradiol stearate Estradiol 17β-stearate 0 ? ?
Estrone E1; 17-Ketoestradiol 11 5.3–38 14
Estrone sulfate E1S; Estrone 3-sulfate 2 0.004 0.002
Estrone glucuronide E1G; Estrone 3-glucuronide ? <0.001 0.0006
Ethinylestradiol EE; 17α-Ethynylestradiol 100 17–150 129
Mestranol EE 3-methyl ether 1 1.3–8.2 0.16
Quinestrol EE 3-cyclopentyl ether ? 0.37 ?
Footnotes: a =
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.


Graphic of the metabolic pathways of estradiol in humans
Estrone glucuronide




17-Epiestriol
16-Epiestriol





CYP450
CYP450



CYP450



unidentified
unidentified
The image above contains clickable links
Description: The
hydroxyl (–OH) groups
. Sources: See template page.

See also

References

  1. ^ a b c d "Human Metabolome Database: Showing metabocard for Estrone glucuronide (HMDB0004483)".
  2. ^
    ISBN 978-3-642-60107-1
    .
  3. ^
    ISBN 978-0-203-48612-2
    .
  4. PMID 23375353
    .
  5. PMID 7169965
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Estrone_glucuronide&oldid=1152581914"