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
1. Zhou, P., Gross, S., Liu, J.H., et al. Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways. FASEB J. 24(12), 4722-4732 (2010).
2. Tang, Y., Xuesen, L., Zhongbo, L., et al. Flavokawain B, a kava chalcone, exhibits robust apoptotic mechanisms on androgen receptor-negative, hormone-refractory prostate cancer cell lines and reduces tumor growth in a preclinical model. Int. J. Cancer 127(8), 1758-1768 (2010).
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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