Structure Database (LMSD)

Common Name
2-Methoxyestradiol-17beta
Systematic Name
2-methoxy-estra-1,3,5(10)-triene-3,17β-diol
Synonyms
LM ID
LMST02010035
Formula
C19H26O3
Exact Mass
Calculate m/z
302.188195
Sum Composition
ST 19:3;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C18 steroids (estrogens) and derivatives [ST0201]

Biological Context

2-methoxy Estradiol (2-ME2) is a natural metabolite formed by CYP450-mediated hydroxylation followed by catechol-O-methyltransferase (COMT) methylation of estradiol. Administration of 2-hydroxy estradiol (2-HE2) to rats results in formation and clearance of 2-ME2 with t½ values of 7.9 and 24.9 minutes, respectively.1 2-ME2 exhibits no affinity for estrogen receptors. 2-ME2 has achieved considerable attention as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1α pathway.2,3,4 The levels of COMT and 2-ME2 are significantly lower in women with severe pre-eclampsia.5

This information has been provided by Cayman Chemical

References

3. Mooberry, S.L. Mechanism of action of 2-methoxyestradiol: New developments. Drug Resist. Updat. 6(6), 355-361 (2003).
2. Zacharia, L.C., Piché, C.A., Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J. Pharmacol. Exp. Ther. 309(3), 1093-1097 (2004).
1. Becker, C.M., Rohwer, N., Funakoshi, T., et al. 2-methoxyestradiol inhibits hypoxia-inducible factor-1α and suppressess growth of lesions in a mouse model of endometriosis. Am. J. Pathol. 172(2), 534-544 (2008).
4. Mooberry, S.L. New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr. Opin. Oncol. 15(6), 425-430 (2003).
5. Kanasaki, K., Palmsten, K., Sugimoto, H., et al. Deficiency in catechol-O-methyltransferase and 2-methoxyoestradiol is associated with pre-eclampsia. Nature 453, 1117-1123 (2008).

Reactions

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String Representations

InChiKey (Click to copy)
CQOQDQWUFQDJMK-SSTWWWIQSA-N
InChi (Click to copy)
InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
SMILES (Click to copy)
[C@]12([H])CC[C@]3(C)[C@H](CC[C@@]3([H])[C@]1([H])CCC1C=C(C(OC)=CC2=1)O)O

Other Databases

Wikipedia
2-Methoxyestradiol
KEGG ID
C05302
HMDB ID
HMDB0000405
CHEBI ID
28955
PubChem CID
66414
Cayman ID
13021
PDB ID
ESM
GuidePharm ID
12058

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 4
Aromatic Rings 1
Rotatable Bonds 1
Van der Waals Molecular Volume 295.37
Topological Polar Surface Area 49.69
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 3.90
Molar Refractivity 85.79

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Updated at
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