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

ChEBI IDCHEBI:70655
ChEBI Name(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone
Stars
ASCII Name(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone
DefinitionA 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.
Last Modified1 October 2014
DownloadsMolfile
FormulaC18H18O5
Net Charge0
Average Mass314.337
Monoisotopic Mass314.11542
SMILESCOc1c(C)c(O)c(C)c(O)c1C(=O)/C=C/c1ccc(O)cc1
InChIInChI=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+
InChIKeyHTDSMOBGCNRBHQ-RMKNXTFCSA-N
Species of MetaboliteComponentSourceComments
Cleistocalyx operculatus (IPNI:82151-3) flower bud (BTO:0000470) DOI (10.1021/np1002753) Combined methanolic extract of dried buds
Roles Classification
Biological Roles:
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:
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 Relation(s)
(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 NumbersSources
Reaxys:21040404Reaxys
Citations