(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655)

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ChEBI Name	(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone

ChEBI ID	CHEBI:70655

ChEBI ASCII Name	(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone

Definition	A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and methyl groups at positions 3' and 5'. Isolated from the buds of Cleistocalyx operculatus, it has been shown to exhibit inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2.

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

Supplier Information

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Formula

C18H18O5

Net Charge

Average Mass

314.33250

Monoisotopic Mass

314.11542

InChI

InChI=1S/C18H18O5/c1-10-16(21)11(2)18(23-3)15(17(10)22)14(20)9-6-12-4-7-13(19)8-5-12/h4-9,19,21-22H,1-3H3/b9-6+

InChIKey

HTDSMOBGCNRBHQ-RMKNXTFCSA-N

SMILES

COc1c(C)c(O)c(C)c(O)c1C(=O)\C=C\c1ccc(O)cc1

Metabolite of Species	Details
Cleistocalyx operculatus (IPNI:82151-3)	Found in flower bud (BTO:0000470). Combined methanolic extract of dried buds See: DOI

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 3.2.1.18 (exo-alpha-sialidase) inhibitor An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.

Application(s):	EC 3.2.1.18 (exo-alpha-sialidase) inhibitor An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.

ChEBI Ontology
Outgoing	(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) has functional parent trans-chalcone (CHEBI:48965) (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425) (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) has role plant metabolite (CHEBI:76924) (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) is a chalcones (CHEBI:23086) (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) is a monomethoxybenzene (CHEBI:25235) (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone (CHEBI:70655) is a polyphenol (CHEBI:26195)

IUPAC Name

(2E)-1-(2,4-dihydroxy-6-methoxy-3,5-dimethylphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Registry Number	Type	Source
21040404	Reaxys Registry Number	Reaxys

Citation	Type	Source
20886838	PubMed citation	Europe PMC

Last Modified

01 October 2014