Structure Database (LMSD)
Common Name
Norwogonin
Systematic Name
Synonyms
3D model of Norwogonin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Norwogonin is a polyhydroxy flavone that has been found in S. baicalensis and has diverse biological activities, including antioxidant, antiviral, and anticancer properties.1,2,3 It scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with IC50 values of 1.24 and 35.61 μg/ml, respectively, in cell-free assays.1 Norwogonin inhibits cytopathic effects induced by enterovirus 71 (EV71) in infected Vero cells (IC50 = 31.83 μg/ml).2 It reduces the viability of MDA-MB-231, BT-549, HCC70, and HCC1806 triple-negative breast cancer (TNBC) cells (IC50s = 32.24, 56.2, 39.05, and 37.3 μM, respectively) but not the non-tumorigenic cell lines MCF-10A and AG11132 (IC50s = >100 μM for both).3 Norwogonin induces cell cycle arrest at the G1 and G2/M phases and increases apoptosis in MDA-MB-231 cells in a concentration-dependent manner.
This information has been provided by Cayman Chemical
References
2. Choi, H.J., Song, H.-H., Lee, J.-S., et al. Inhibitory effects of Norwogonin, Oroxylin A, and Mosloflavone on Enterovirus 71. Biomol. Ther. (Seoul) 24(5), 552-558 (2016).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
ZFKKRRMUPBBYRS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O5/c16-9-6-11(18)14(19)15-13(9)10(17)7-12(20-15)8-4-2-1-3-5-8/h1-7,16,18-19H
SMILES (Click to copy)
C1(O)=C(O)C2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1
Other Databases
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
221.11
Topological Polar Surface Area
90.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.48
Molar Refractivity
73.02
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