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

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ChEBI Name	(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

ChEBI ID	CHEBI:70018

ChEBI ASCII Name	(2S)-5,7,3'-trihydroxy-4'-methoxy-8-(3''-methylbut-2''-enyl)-flavonone

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C21H22O6

Net Charge

Average Mass

370.39580

Monoisotopic Mass

370.14164

InChI

InChI=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

InChIKey

MDRKJMLXLVCUIU-IBGZPJMESA-N

SMILES

COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O)cc(O)c(CC=C(C)C)c2O1

Metabolite of Species	Details
Macaranga conifera (NCBI:txid109817)	Methanol-Dichloromethane (1:1) extract of dried, ground plant material 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. breast cancer resistance protein inhibitor Any inhibitor of breast cancer resistance protein (ABCG2).

ChEBI Ontology
Outgoing	(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)hesperetin	ChEBI

Registry Number	Type	Source
21312873	Reaxys Registry Number	Reaxys

Citation	Type	Source
21275386	PubMed citation	Europe PMC

Last Modified

06 April 2018