Structure Database (LMSD)
Common Name
Wogonin
Systematic Name
5,7-Dihydroxy-8-methoxyflavone
Synonyms
3D model of Wogonin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Wogonin is an O-methylated flavonoid isolated from the root of the traditional Chinese herb S. baicalensis with anti-inflammatory, antioxidant, and neuroprotective activities.1 At concentrations of 5-50 μM, wogonin inhibits inflammatory activation of cultured brain microglia by diminishing LPS-induced TNF-α, IL-1β, and nitric oxide production.2 Wogonin at 75 μM demonstrates tumor therapeutic potential inducing sub-G1 phase apoptosis through activation of caspase-3 activity in human osteocarcinoma cell lines.3
This information has been provided by Cayman Chemical
References
1. Lee, H., Kim, Y.O., Kim, H., et al. Flavonoid wogonin from medicinal herb is neuroprotective by inhibiting inflammatory activation of microglia. FASEB J. 17(13), 1943-1944 (2003).
2. Huang, W.H., Chien, P.Y., Yang, C.H., et al. Novel synthesis of flavonoids of Scutellaria baicalensis GEORGI. Chem. Pharm. Bull. (Tokyo) 51(3), 339-340 (2003).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
XLTFNNCXVBYBSX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
SMILES (Click to copy)
C1(O)=C(OC)C2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
238.41
Topological Polar Surface Area
79.90
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
3.78
Molar Refractivity
77.91
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Updated at
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