Structure Database (LMSD)

Common Name
Demethylwedelolactone
Systematic Name
Synonyms
  • Norwedelolactone
LM ID
LMPK12090041
Formula
C15H8O7
Exact Mass
Calculate m/z
300.027005
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Coumestan flavonoids [PK1209]

Biological Context

Demethylwedelolactone (DWL) is a coumestan, originally isolated from E. alba, with diverse biological activities.1,2,3,4 It reduces cytotoxicity induced by CCL4 and galactosamine (GaIN) in rat hepatocytes in a dose-dependent manner.1 DWL inhibits trypsin with an IC50 value of 3.0 μg/ml in vitro.2 It is the major constituent in purified butanolic extracts of E. prostrata which inhibit lethal and hemorrhagic activities of C. rhodostoma venom.3 DWL also inhibits anchorage-independent cell growth of MDA-MB-231 breast cancer cells and decreases the number of lung metastases in an MDA-MB-231 xenograft model in nude mice.4

This information has been provided by Cayman Chemical

References

1. Lee, Y.-J., Lin, W.-L., Chen, N.-F., et al. Demethylwedelolactone derivatives inhibit invasive growth in vitro and lung metastasis of MDA-MB-231 breast cancer cells in nude mice. Eur. J. Med. Chem. 56(1), 631-637 (2012).
2. Pithayanukul, P., Laovachirasuwan, S., Bavovada, R., et al. Anti-venom potential of butanolic extract of Eclipta prostrata against Malayan pit viper venom. J. Ethnaopharmacol. 90(2-3), 347-352 (2004).
3. Syed, S.D., Deepak, M., Yogisha, S., et al. Trypsin inhibitory effect of wedelolactone and demethylwedelolactone. Phytother. Res. 17(4), 420-421 (2003).
4. Wagner, H., Geyer, B., Kiso, Y., et al. Coumestans as the main active principles of the liver drugs Eclipta alba and Wedelia calendulacea. Planta Med. 5, 370-374 (1986).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
LUTYTNLPIUCKBJ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H8O7/c16-5-1-9(19)13-11(2-5)22-15(20)12-6-3-7(17)8(18)4-10(6)21-14(12)13/h1-4,16-19H
SMILES (Click to copy)
C1(O)C=C(O)C2C3OC4=CC(O)=C(O)C=C4C=3C(=O)OC=2C=1

Other Databases

HMDB ID
HMDB0128455
CHEBI ID
191036
METABOLOMICS ID
FLIEACNS0001
PubChem CID
5489605
Cayman ID
11703

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 4
Aromatic Rings 4
Rotatable Bonds 0
Van der Waals Molecular Volume 215.43
Topological Polar Surface Area 124.27
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 7
logP 3.41
Molar Refractivity 76.53

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