Structure Database (LMSD)

Common Name
Flavokawin C
Systematic Name
Synonyms
LM ID
LMPK12120320
Formula
Exact Mass
Calculate m/z
300.099775
Status
Curated


Classification

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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