Structure Database (LMSD)
Common Name
Isobavachalcone
Systematic Name
2',4,4'-Trihydroxy-3'-(3-methyl-2-butenyl)chalcone
Synonyms
- Corylifolinin
3D model of Isobavachalcone
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
Isobavachalcone (IBC) is a chalcone and flavonoid originally isolated from P. corylifolia and has diverse biological activities.1,2 It is active against C. albicans and C. neoformans (IC50s = 3 and 7 µg/ml, respectively), as well as T. rubrum and M. audouinii (MIC = 1.2 µg/ml for both).1 IBC is active against various Bacillus, Streptococcus, and Proteus species, as well as K. pneumoniae, P. aeruginosa, S. typhi, M. morganii, E. aerogenes, C. freundii, and E. cloacae (MICs = 4.9-39.1 µg/ml). It induces mitochondrial-mediated apoptosis in IMR-32 and NB-39 human neuroblastoma cells and inhibits the proliferation of OVCAR-8 ovarian, PC3 prostate, MCF-7 breast, and A549 lung cancer cell lines. IBC (50 mg/kg) reduces dopaminergic neuronal cell death and increases the stay time in the rotarod test in a mouse model of MPTP-induced Parkinson’s disease.2
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)
DUWPGRAKHMEPCM-IZZDOVSWSA-N
InChi (Click to copy)
InChI=1S/C20H20O4/c1-13(2)3-9-16-19(23)12-10-17(20(16)24)18(22)11-6-14-4-7-15(21)8-5-14/h3-8,10-12,21,23-24H,9H2,1-2H3/b11-6+
SMILES (Click to copy)
C1(O)C=CC(C(=O)/C=C/C2C=CC(O)=CC=2)=C(O)C=1C/C=C(\C)/C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
2
Aromatic Rings
2
Rotatable Bonds
5
Van der Waals Molecular Volume
319.44
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
4.21
Molar Refractivity
94.38
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Updated at
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