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4-Methoxyestriol

From Wikipedia, the free encyclopedia
4-Methoxyestriol
Names
IUPAC name
4-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
Systematic IUPAC name
(1R,2R,3aS,3bR,9bS,11aS)-6-Methoxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
Other names
4-MeO-E3
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H26O4/c1-19-8-7-11-10-5-6-15(20)17(23-2)13(10)4-3-12(11)14(19)9-16(21)18(19)22/h5-6,11-12,14,16,18,20-22H,3-4,7-9H2,1-2H3/t11-,12-,14+,16-,18+,19+/m1/s1
    Key: MTZUPVFOGAXGJG-JUVWIQMMSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4OC)O
Properties
C19H26O4
Molar mass318.413 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

4-Methoxyestriol (4-MeO-E3) is anendogenousestrogenmetabolite.[1][2][3][4] It is the 4-methylether of4-hydroxyestriol and a metabolite ofestriol and 4-hydroxyestriol.[1][2][3] 4-Methoxyestriol has very lowaffinities for theestrogen receptors.[4] Itsrelative binding affinities (RBAs) forestrogen receptor alpha (ERα) andestrogen receptor beta (ERβ) are both about 1% of those ofestradiol.[4] For comparison, estriol had RBAs of 11% and 35%, respectively.[4]

See also

[edit]

References

[edit]
  1. ^abGerhardt K, Ludwig-Köhn H, Henning HV, Remberg G, Zeeck A (February 1989). "Identification of oestrogen metabolites in human urine by capillary gas chromatography and mass spectrometry".Biomed. Environ. Mass Spectrom.18 (2):87–95.doi:10.1002/bms.1200180202.PMID 2706375.
  2. ^abGaikwad NW (May 2013). "Ultra performance liquid chromatography-tandem mass spectrometry method for profiling of steroid metabolome in human tissue".Anal. Chem.85 (10):4951–60.doi:10.1021/ac400016e.PMID 23597399.
  3. ^abFujii Y, Teranishi M, Nakada K, Yamazaki M, Kishida S, Miyabo S (February 1992)."Radioimmunoassay for the determination of 2-methoxyestriol concentration in plasma of pregnant women".Chem. Pharm. Bull.40 (2):410–3.doi:10.1248/cpb.40.410.PMID 1606638.
  4. ^abcdZhu BT, Han GZ, Shim JY, Wen Y, Jiang XR (September 2006). "Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding".Endocrinology.147 (9):4132–50.doi:10.1210/en.2006-0113.PMID 16728493.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others


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