Structure Database (LMSD)
Common Name
Flavokawin B
Systematic Name
Synonyms
3D model of Flavokawin B
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 B is a natural chalcone first isolated from extracts of kava roots. It induces apoptosis in androgen receptor-negative, hormone-refractory prostate cancer cell lines (IC50s = 32, 48, 6.2, and 3.9 µM for LAPC4, LNCaP, PC-3, and DU145 cells, respectively, treated for 48 hours), with increased expression of the proapoptotic protein Bim.1 Flavokawain B increases Bim expression and inhibits growth of DU145 xenografts in mice.1 It also increases Bim expression, promotes apoptosis, and induces cell cycle arrest in uterine leiomyosarcoma cells.2 However, flavokawain B is hepatotoxic, triggering oxidative stress, inhibiting NF-κB signaling, and activating MAPK pathways, culminating in HepG2 and L-02 cell death (LD50s = 15 and 32 µM, respectively).3
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)
QKQLSQLKXBHUSO-CMDGGOBGSA-N
InChi (Click to copy)
InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
SMILES (Click to copy)
C1(OC)=CC(OC)=C(C(=O)/C=C/C2C=CC=CC=2)C(O)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
2
Aromatic Rings
2
Rotatable Bonds
5
Van der Waals Molecular Volume
270.18
Topological Polar Surface Area
55.76
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
4
logP
3.31
Molar Refractivity
81.02
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Updated at
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