Structure Database (LMSD)
Common Name
Wedelolactone
Systematic Name
1,8,9-Trihydroxy-3-methoxycoumestan
Synonyms
- 5,11,12-Trihydroxy-7-methoxycoumestan
3D model of Wedelolactone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Wedelolactone is a natural coumestan originally isolated from plants used in herbal therapies. It inhibits NF-κB signaling at the level of IKK action, resulting in suppression of NF-κB-mediated gene expression at concentrations of 1-100 µM.1,2,3 Wedelolactone can also inhibit hepatitis C virus NS5B RNA-dependent RNA polymerase in vitro (IC50 = 36 µM), STAT1 dephosphorylation (50 µM), and EZH2-EED interactions (Kd = 2.8 µM).4,5,6 Prolonged incubation of HepG2 liver cells with wedelolactone alters lipid metabolism through increased expression of AMPK, PPARα, lipoprotein lipase, and low-density lipoprotein receptor.7
This information has been provided by Cayman Chemical
References
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
XQDCKJKKMFWXGB-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3
SMILES (Click to copy)
C1(OC)=CC2OC(=O)C3C4C=C(O)C(O)=CC=4OC=3C=2C(O)=C1
Other Databases
Wikipedia
KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
4
Aromatic Rings
4
Rotatable Bonds
1
Van der Waals Molecular Volume
232.73
Topological Polar Surface Area
113.27
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
7
logP
3.72
Molar Refractivity
81.42
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Updated at
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