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CHEBI:65439 - artocarpin

ChEBI IDCHEBI:65439
ChEBI Nameartocarpin
Stars
DefinitionA trihydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 2', and 4', a methoxy group at position 7, a prenyl group at position 3 and a (1E)-3-methylbut-1-enyl group at position 6. Isolated from Artocarpus heterophyllus and Artocarpus integrifolia, it exhibits antineoplastic activity.
Last Modified30 January 2013
DownloadsMolfile
FormulaC26H28O6
Net Charge0
Average Mass436.504
Monoisotopic Mass436.18859
SMILESCOc1cc2oc(-c3ccc(O)cc3O)c(CC=C(C)C)c(=O)c2c(O)c1/C=C/C(C)C
InChIInChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+
InChIKeyKRGDFVQWQJIMEK-RMKNXTFCSA-N
Species of MetaboliteComponentSourceComments
Artocarpus (ncbitaxon:3488) xylem (BTO:0001468) Article (J SCI IND RES,1956,15B,183) Previous component: wood;
Artocarpus heterophyllus (ncbitaxon:3489) root (BTO:0001188) DOI (10.1016/0031-9422(95)00135-T)
Artocarpus chama (ncbitaxon:709040) root (BTO:0001188) PubMed (15165133)
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)
artocarpin (CHEBI:65439) has role antineoplastic agent (CHEBI:35610)
artocarpin (CHEBI:65439) has role metabolite (CHEBI:25212)
artocarpin (CHEBI:65439) is a monomethoxyflavone (CHEBI:25401)
artocarpin (CHEBI:65439) is a trihydroxyflavone (CHEBI:27116)
IUPAC Name 
2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Synonyms  Source
5-hydroxy-7-methoxy-3-(3-methyl-2-butenyl)-6-(3-methyl-1-butenyl)-2-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
2',4',5-trihydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)flavoneLIPID MAPS
Manual XrefsDatabases
LMPK12110898LIPID MAPS
Registry NumbersSources
Reaxys:62644Reaxys
Citations