4-Methoxyestriol

4-Methoxyestriol (4-MeO-E3) is an endogenous estrogen metabolite.[1][2][3][4] It is the 4-methyl ether of 4-hydroxyestriol and a metabolite of estriol and 4-hydroxyestriol.[1][2][3] 4-Methoxyestriol has very low affinities for the estrogen receptors.[4] Its relative binding affinities (RBAs) for the ERα and ERβ are both about 1% of those of estradiol.[4] For comparison, estriol had RBAs of 11% and 35%, respectively.[4]

4-Methoxyestriol
Names
IUPAC name
(8R,9S,13S,14S,16R,17R)-4-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
Other names
4-MeO-E3; 4-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
Identifiers
3D model (JSmol)
ChemSpider
Properties
C19H26O4
Molar mass 318.413 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Gerhardt 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. Gaikwad 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. Fujii 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. Zhu 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.



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