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Estradiol 3-glucuronide 17β-sulfate

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Estradiol 3-glucuronide 17β-sulfate
Names
IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S,17S)-13-methyl-17-sulfooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
Other names
E2-3G-17S
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C24H32O11S/c1-24-9-8-14-13-5-3-12(33-23-20(27)18(25)19(26)21(34-23)22(28)29)10-11(13)2-4-15(14)16(24)6-7-17(24)35-36(30,31)32/h3,5,10,14-21,23,25-27H,2,4,6-9H2,1H3,(H,28,29)(H,30,31,32)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1
    Key: XZXBPAODZJETKT-QXYWQCSFSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OS(=O)(=O)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
C24H32O11S
Molar mass 528.57 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Estradiol 3-glucuronide 17β-sulfate (E2-3G-17S) is an endogenous estrogen conjugate and metabolite of estradiol.[1][2] It is related to estradiol 3-sulfate and estradiol 17β-glucuronide.[1][2] Estradiol 3-glucuronide 17β-sulfate has 0.0001% of the relative binding affinity of estradiol for the ERα, one of the two estrogen receptors (ERs).[3] It shows less than one million-fold lower potency in activating the estrogen receptors relative to estradiol in vitro.[4]

See also

References

  1. ^ a b Isobe T, Shiraishi H, Yasuda M, Shinoda A, Suzuki H, Morita M (January 2003). "Determination of estrogens and their conjugates in water using solid-phase extraction followed by liquid chromatography-tandem mass spectrometry". J Chromatogr A. 984 (2): 195–202. doi:10.1016/s0021-9673(02)01851-4. PMID 12564690.
  2. ^ a b Katayama M, Matsuda Y, Shimokawa K, Kaneko S (June 2003). "Simultaneous determination of 16 estrogens, dehydroepiandrosterone and their glucuronide and sulfate conjugates in serum using sodium cholate micelle capillary electrophoresis". Biomed. Chromatogr. 17 (4): 263–7. doi:10.1002/bmc.236. PMID 12833391.
  3. ^ Durmaz V, Schmidt S, Sabri P, Piechotta C, Weber M (October 2013). "Hands-off linear interaction energy approach to binding mode and affinity estimation of estrogens". J Chem Inf Model. 53 (10): 2681–8. doi:10.1021/ci400392p. PMID 24063761.
  4. ^ Coldham NG, Dave M, Sivapathasundaram S, McDonnell DP, Connor C, Sauer MJ (July 1997). "Evaluation of a recombinant yeast cell estrogen screening assay". Environ. Health Perspect. 105 (7): 734–42. doi:10.1289/ehp.97105734. PMC 1470103. PMID 9294720.



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