Structure Database (LMSD)

Common Name
Isobavachalcone
Systematic Name
2',4,4'-Trihydroxy-3'-(3-methyl-2-butenyl)chalcone
Synonyms
  • Corylifolinin
LM ID
LMPK12120039
Formula
Exact Mass
Calculate m/z
324.13616
Status
Curated

Classification

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

KEGG ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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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