fbpx
Wikipedia

Estradiol 3-glucuronide 17β-sulfate

February 16, 2024

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]

Estradiol 3-glucuronide 17β-sulfate
Names
IUPAC name
17β-(Sulfooxy)estra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(1S,3aS,3bR,9bS,11aS)-11a-methyl-1-(sulfooxy)-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid
Other names
E2-3G-17S
Identifiers
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:79720
ChemSpider
  • 10128415
KEGG
  • C15207
  • 11954120
  • 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).

See also edit

References edit

  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.



 

This article about a steroid is a stub. You can help Wikipedia by expanding it.

February 16, 2024
estradiol, glucuronide, 17β, sulfate, endogenous, estrogen, conjugate, metabolite, estradiol, related, estradiol, sulfate, estradiol, 17β, glucuronide, 0001, relative, binding, affinity, estradiol, erα, estrogen, receptors, shows, less, than, million, fold, lo. Estradiol 3 glucuronide 17b sulfate E2 3G 17S is an endogenous estrogen conjugate and metabolite of estradiol 1 2 It is related to estradiol 3 sulfate and estradiol 17b glucuronide 1 2 Estradiol 3 glucuronide 17b sulfate has 0 0001 of the relative binding affinity of estradiol for the ERa 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 Estradiol 3 glucuronide 17b sulfate NamesIUPAC name 17b Sulfooxy estra 1 3 5 10 trien 3 yl b D glucopyranosiduronic acidSystematic IUPAC name 2S 3S 4S 5R 6S 3 4 5 Trihydroxy 6 1S 3aS 3bR 9bS 11aS 11a methyl 1 sulfooxy 2 3 3a 3b 4 5 9b 10 11 11a decahydro 1H cyclopenta a phenanthren 7 yl oxy oxane 2 carboxylic acidOther names E2 3G 17SIdentifiers3D model JSmol Interactive imageChEBI CHEBI 79720ChemSpider 10128415KEGG C15207PubChem CID 11954120InChI 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 s1Key XZXBPAODZJETKT QXYWQCSFSA NSMILES 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 OPropertiesChemical formula C 24H 32O 11SMolar mass 528 57 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSee also editCatechol estrogen Estrogen conjugate Lipoidal estradiol List of estrogen esters Estradiol estersReferences edit 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 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 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 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Estradiol 3 glucuronide 17b sulfate amp oldid 1152576380, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.