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Estradiol 3-glucuronide 17β-sulfate

From Wikipedia, the free encyclopedia
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)
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 mass528.57 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Estradiol 3-glucuronide 17β-sulfate (E2-3G-17S) is anendogenousestrogen conjugate andmetabolite ofestradiol.[1][2] It is related toestradiol 3-sulfate andestradiol 17β-glucuronide.[1][2] Estradiol 3-glucuronide 17β-sulfate has 0.0001% of therelative binding affinity of estradiol for theERα, one of the twoestrogen receptors (ERs).[3] It shows less than one million-fold lowerpotency in activating theestrogen receptors relative to estradiolin vitro.[4]

See also

[edit]

References

[edit]
  1. ^abIsobe 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. ^abKatayama 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.


Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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