Structure Database (LMSD)

Common Name
Flavokawin B
Systematic Name
Synonyms
LM ID
LMPK12120246
Formula
Exact Mass
Calculate m/z
284.10486
Status
Curated


Classification

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

HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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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