CHEBI:66648 - macaranone A

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ChEBI Name macaranone A
ChEBI ID CHEBI:66648
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C30H34O7
Net Charge 0
Average Mass 506.58680
Monoisotopic Mass 506.23045
InChI InChI=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+
InChIKey OAZFFUNCFJOTIQ-VCHYOVAHSA-N
SMILES CC(C)=CCC\C(C)=C\Cc1c(O)c(O)c(CC=C(C)C)cc1-c1oc2cc(O)cc(O)c2c(=O)c1O
Metabolite of Species Details
Macaranga sampsonii (NCBI:txid524430) Found in leaf (BTO:0000713). 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 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 Number Type Source
19726973 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
19420781 PubMed citation Europe PMC
Last Modified
28 March 2013