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CHEBI:70018 - (2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

ChEBI IDCHEBI:70018
ChEBI Name(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone
Stars
ASCII Name(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone
DefinitionA trihydroxyflavanone that is hesperetin substituted by a prenyl group at position 8. Isolated from Macaranga conifera, it exhibits inhibitory activity against breast cancer resistance protein.
Last Modified6 April 2018
DownloadsMolfile
FormulaC21H22O6
Net Charge0
Average Mass370.401
Monoisotopic Mass370.14164
SMILESCOc1ccc([C@@H]2CC(=O)c3c(O)cc(O)c(CC=C(C)C)c3O2)cc1O
InChIInChI=1S/C21H22O6/c1-11(2)4-6-13-14(22)9-16(24)20-17(25)10-19(27-21(13)20)12-5-7-18(26-3)15(23)8-12/h4-5,7-9,19,22-24H,6,10H2,1-3H3/t19-/m0/s1
InChIKeyMDRKJMLXLVCUIU-IBGZPJMESA-N
Species of MetaboliteComponentSourceComments
Macaranga conifera (ncbitaxon:109817) - PubMed (21275386) Methanol-Dichloromethane (1:1) extract of dried, ground plant material
Roles Classification
Biological Roles:
breast cancer resistance protein inhibitor  Any inhibitor of breast cancer resistance protein (ABCG2).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) has functional parent hesperetin (CHEBI:28230)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) has role breast cancer resistance protein inhibitor (CHEBI:72771)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) has role metabolite (CHEBI:25212)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) is a 3'-hydroxyflavanones (CHEBI:48024)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) is a 4'-methoxyflavanones (CHEBI:140332)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) is a monomethoxyflavanone (CHEBI:38738)
(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone (CHEBI:70018) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name 
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
Synonym  Source
8-(3,3-dimethylallyl)hesperetinChEBI
Registry NumbersSources
Reaxys:21312873Reaxys
Citations