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CHEBI:66643 - maackiaflavanone A

ChEBI IDCHEBI:66643
ChEBI Namemaackiaflavanone A
Stars
DefinitionA dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 2', a methoxy group at position 7, a prenyl group at position 8 and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 4' and 5'. Isolated from the stem barks of Maackia amurensis, it exhibits cytotoxicity against human cancer cell lines.
Last Modified28 March 2013
DownloadsMolfile
FormulaC26H28O6
Net Charge0
Average Mass436.504
Monoisotopic Mass436.18859
SMILESCOc1cc(O)c2c(c1CC=C(C)C)O[C@H](c1cc3c(cc1O)OC(C)(C)C=C3)CC2=O
InChIInChI=1S/C26H28O6/c1-14(2)6-7-16-22(30-5)12-19(28)24-20(29)13-23(31-25(16)24)17-10-15-8-9-26(3,4)32-21(15)11-18(17)27/h6,8-12,23,27-28H,7,13H2,1-5H3/t23-/m0/s1
InChIKeySMMHWUYJGIKYEW-QHCPKHFHSA-N
Species of MetaboliteComponentSourceComments
Maackia amurensis (ncbitaxon:37501) stem (BTO:0001300) PubMed (19252325) Previous component: stem bark;
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
maackiaflavanone A (CHEBI:66643) has role antineoplastic agent (CHEBI:35610)
maackiaflavanone A (CHEBI:66643) has role metabolite (CHEBI:25212)
maackiaflavanone A (CHEBI:66643) is a dihydroxyflavanone (CHEBI:38749)
maackiaflavanone A (CHEBI:66643) is a monomethoxyflavanone (CHEBI:38738)
IUPAC Name 
(2S)-5,7'-dihydroxy-7-methoxy-2',2'-dimethyl-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one
Synonym  Source
(2S)-5,2'-dihydroxy-7-methoxy-8-(3-methylbut-2-enyl)-2''',2'''-dimethylpyrano[5''',6''':5',4']ChEBI
Manual XrefsDatabases
CN101434592Patent
Registry NumbersSources
Reaxys:19598947Reaxys
Citations