2-Methoxyestriol

Chemical compound From Wikipedia, the free encyclopedia

2-Methoxyestriol (2-MeO-E3) is an endogenous estrogen metabolite.[1][2][3] It is specifically a metabolite of estriol and 2-hydroxyestriol.[1][2][3] It has negligible affinity for the estrogen receptors and no estrogenic activity.[4] However, 2-methoxyestriol does have some non-estrogen receptor-mediated cholesterol-lowering effects.[5]

More information Estrogen, ERTooltip Estrogen receptor RBATooltip relative binding affinity (%) ...
Selected biological properties of endogenous estrogens in rats
EstrogenERTooltip Estrogen receptor RBATooltip relative binding affinity (%)Uterine weight (%)UterotrophyLHTooltip Luteinizing hormone levels (%)SHBGTooltip Sex hormone-binding globulin RBATooltip relative binding affinity (%)
Control–100–100–
Estradiol (E2)100506 ± 20+++12–19100
Estrone (E1)11 ± 8490 ± 22+++?20
Estriol (E3)10 ± 4468 ± 30+++8–183
Estetrol (E4)0.5 ± 0.2?Inactive?1
17α-Estradiol4.2 ± 0.8????
2-Hydroxyestradiol24 ± 7285 ± 8+b31–6128
2-Methoxyestradiol0.05 ± 0.04101Inactive?130
4-Hydroxyestradiol45 ± 12????
4-Methoxyestradiol1.3 ± 0.2260++?9
4-Fluoroestradiola180 ± 43?+++??
2-Hydroxyestrone1.9 ± 0.8130 ± 9Inactive110–1428
2-Methoxyestrone0.01 ± 0.00103 ± 7Inactive95–100120
4-Hydroxyestrone11 ± 4351++21–5035
4-Methoxyestrone0.13 ± 0.04338++65–9212
16α-Hydroxyestrone2.8 ± 1.0552 ± 42+++7–24<0.5
2-Hydroxyestriol0.9 ± 0.3302+b??
2-Methoxyestriol0.01 ± 0.00?Inactive?4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: a = Synthetic (i.e., not endogenous). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: [6][7][8][9][10][11][12][13][14]
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Quick facts Names, Identifiers ...
2-Methoxyestriol
Names
IUPAC name
2-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
Systematic IUPAC name
(1R,2R,3aS,3bR,9bS,11aS)-8-Methoxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol
Other names
2-MeO-E3
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C19H26O4/c1-19-6-5-11-12(14(19)9-16(21)18(19)22)4-3-10-7-15(20)17(23-2)8-13(10)11/h7-8,11-12,14,16,18,20-22H,3-6,9H2,1-2H3/t11-,12+,14-,16+,18-,19-/m0/s1
    Key: PEXPJFWTSZLEAQ-YSYMNNNUSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=CC(=C(C=C34)OC)O
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).
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