CHEBI:66643 - maackiaflavanone A

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ChEBI Name maackiaflavanone A
ChEBI ID CHEBI:66643
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H28O6
Net Charge 0
Average Mass 436.49690
Monoisotopic Mass 436.18859
InChI InChI=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
InChIKey SMMHWUYJGIKYEW-QHCPKHFHSA-N
SMILES COc1cc(O)c2C(=O)C[C@H](Oc2c1CC=C(C)C)c1cc2C=CC(C)(C)Oc2cc1O
Metabolite of Species Details
Maackia amurensis (NCBI:txid37501) Found in stem (BTO:0001300). Previous component: stem bark; See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
CN101434592 Patent
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Registry Number Type Source
19598947 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
19252325 PubMed citation Europe PMC
Last Modified
28 March 2013