Chemistry:4-Methoxyestriol
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| Names | |
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| IUPAC name
4-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| 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 | |
Tracking categories (test):
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 estrogen receptor alpha (ERα) and estrogen receptor beta (ERβ) are both about 1% of those of estradiol.[4] For comparison, estriol had RBAs of 11% and 35%, respectively.[4]
See also
References
- ↑ 1.0 1.1 "Identification of oestrogen metabolites in human urine by capillary gas chromatography and mass spectrometry". Biomed. Environ. Mass Spectrom. 18 (2): 87–95. February 1989. doi:10.1002/bms.1200180202. PMID 2706375.
- ↑ 2.0 2.1 "Ultra performance liquid chromatography-tandem mass spectrometry method for profiling of steroid metabolome in human tissue". Anal. Chem. 85 (10): 4951–60. May 2013. doi:10.1021/ac400016e. PMID 23597399.
- ↑ 3.0 3.1 "Radioimmunoassay for the determination of 2-methoxyestriol concentration in plasma of pregnant women". Chem. Pharm. Bull. 40 (2): 410–3. February 1992. doi:10.1248/cpb.40.410. PMID 1606638.
- ↑ 4.0 4.1 4.2 4.3 "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. September 2006. doi:10.1210/en.2006-0113. PMID 16728493.
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