Structure Database (LMSD)
Common Name
Flavokawin C
Systematic Name
Synonyms
3D model of Flavokawin C
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Flavokawain C is a chalcone that has been found in kava and has enzyme inhibitory and anticancer activities.1,2,3 It inhibits collagenase and elastase in cell-free assays (IC50s = 62.05 and 17.6 µM, respectively).1 It is cytotoxic to HCT116, HT-29, MCF-7, A549, and Ca Ski cancer cells (IC50s = 12.75, 39, 47.63, 40.28, and 39.88 µM, respectively).2 Flavokawain C (20, 40, and 60 µM) induces apoptosis and cell cycle arrest at the G1 phase in HCT116 cells. In vivo, flavokawain C (1 and 3 mg/kg) reduces tumor volume and induces intratumoral necrosis and apoptosis in an HCT116 mouse xenograft model.3
This information has been provided by Cayman Chemical
References
1. Wei, L., Liao, Z., Ma, H., et al. Antioxidant properties, anti- SARS-CoV-2 study, collagenase and elastase inhibition effects, anti-human lung cancer potential of some phenolic compounds. J. Indian Chem. Soc. 99(4), 100416 (2022).
3. Phang, C.-W., Malek, S.N.A., and Karsani, S.A. Flavokawain C exhibits anti-tumor effects on in vivo HCT 116 xenograft and identification of its apoptosis-linked serum biomarkers via proteomic analysis. Biomed. Pharmacother. 137, 110846 (2021).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
UXUFMIJZNYXWDX-VMPITWQZSA-N
InChi (Click to copy)
InChI=1S/C17H16O5/c1-21-13-9-15(20)17(16(10-13)22-2)14(19)8-5-11-3-6-12(18)7-4-11/h3-10,18,20H,1-2H3/b8-5+
SMILES (Click to copy)
C1(OC)=CC(OC)=C(C(=O)/C=C/C2C=CC(O)=CC=2)C(O)=C1
Other Databases
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
2
Aromatic Rings
2
Rotatable Bonds
5
Van der Waals Molecular Volume
278.97
Topological Polar Surface Area
75.99
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
3.01
Molar Refractivity
82.68
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Updated at
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