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CHEBI:66648 - macaranone A

ChEBI IDCHEBI:66648
ChEBI Namemacaranone A
Stars
DefinitionA pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 7, 3' and 4', a geranyl group at position 2' and a prenyl group at position 5'. Isolated from the leaves of Macaranga sampsonii, it exhibits cytotoxicity against several human cancer cell lines.
Last Modified28 March 2013
DownloadsMolfile
FormulaC30H34O7
Net Charge0
Average Mass506.595
Monoisotopic Mass506.23045
SMILESCC(C)=CCC/C(C)=C/Cc1c(-c2oc3cc(O)cc(O)c3c(=O)c2O)cc(CC=C(C)C)c(O)c1O
InChIInChI=1S/C30H34O7/c1-16(2)7-6-8-18(5)10-12-21-22(13-19(11-9-17(3)4)26(33)27(21)34)30-29(36)28(35)25-23(32)14-20(31)15-24(25)37-30/h7,9-10,13-15,31-34,36H,6,8,11-12H2,1-5H3/b18-10+
InChIKeyOAZFFUNCFJOTIQ-VCHYOVAHSA-N
Species of MetaboliteComponentSourceComments
Macaranga sampsonii (ncbitaxon:524430) leaf (BTO:0000713) PubMed (19420781)
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)
macaranone A (CHEBI:66648) has role antineoplastic agent (CHEBI:35610)
macaranone A (CHEBI:66648) has role metabolite (CHEBI:25212)
macaranone A (CHEBI:66648) is a flavonols (CHEBI:28802)
macaranone A (CHEBI:66648) is a pentahydroxyflavone (CHEBI:25883)
IUPAC Name 
2-{2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl}-3,5,7-trihydroxy-4H-chromen-4-one
Registry NumbersSources
Reaxys:19726973Reaxys
Citations