Structure Database (LMSD)

Common Name
2-Methoxyestrone
Systematic Name
2-methoxy,3-hydroxy-estra-1,3,5(10)-trien-17-one
Synonyms
LM ID
LMST02010033
Formula
C19H24O3
Exact Mass
Calculate m/z
300.172545
Sum Composition
ST 19:4;O3
Status
Curated
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Classification

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

Biological Context

2-methoxy Estrone is an active metabolite of the endogenous estrogen estrone .1 It is formed from estrone by catechol-O-methyltransferase (COMT). 2-methoxy Estrone inhibits the proliferation of isolated bovine brain-derived capillary endothelial cells (IC50 = 11.5 µM).2 It increases the levels of 6-keto prostaglandin F1α (6-keto PGF1α) in human umbilical vein endothelial cells (HUVECs) when used at concentrations of 0.001, 0.01, and 0.1 µM.3 2-methoxy Estrone (0.5 mg/kg) reduces ovariectomy-induced increases in serum cholesterol in rats.4

This information has been provided by Cayman Chemical

References

1. Seeger, H., Mueck, A.O., and Lippert, T.H. Effect of estradiol metabolites on prostacyclin synthesis in human endothelial cell cultures. Life Sci. 65(13), PL167-PL170 (1999).
2. Liu, D., and Bachmann, K.A. An investigation of the relationship between estrogen, estrogen metabolites and blood cholesterol levels in ovariectomized rats. J. Pharmacol. Exp. Ther. 286(1), 561-568 (1998).
3. Fotsis, T., Zhang, Y., Pepper, M.S., et al. The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growth. Nature 368(6468), 237-239 (1994).
4. Dawling, S., Roodi, N., Mernaugh, R.L., et al. Catechol-O-methyltransferase (COMT)-mediated metabolism of catechol estrogens: Comparison of wild-type and variant COMT isoforms. Cancer Res. 61(18), 6716-6722 (2001).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Catechol-O-methyltransferase (COMT)-mediated metabolism of catechol estrogens: comparison of wild-type and variant COMT isoforms.,
Cancer Res, 2001
Pubmed ID: 11559542

String Representations

InChiKey (Click to copy)
WHEUWNKSCXYKBU-QPWUGHHJSA-N
InChi (Click to copy)
InChI=1S/C19H24O3/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/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1
SMILES (Click to copy)
[C@]12([H])CC[C@]3(C)C(CC[C@@]3([H])[C@]1([H])CCC1C=C(C(OC)=CC2=1)O)=O

Other Databases

KEGG ID
C05299
HMDB ID
HMDB0000010
CHEBI ID
1189
PubChem CID
440624
Cayman ID
34155

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 4
Aromatic Rings 1
Rotatable Bonds 1
Van der Waals Molecular Volume 292.73
Topological Polar Surface Area 46.53
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 3.83
Molar Refractivity 84.28

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Created at
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Updated at
28th Feb 2025