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CHEBI:70659 - 2',4'-dihydroxy-3'-methyl-6'-methoxychalcone

Default Structure
ChEBI IDCHEBI:70659
ChEBI Name2',4'-dihydroxy-3'-methyl-6'-methoxychalcone
Stars
DefinitionA member of the class of chalcones that is trans-chalcone substituted by a methyl group at position 3', hydroxy groups at positions 2' and 4' and a methoxy group at position 6'. 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
FormulaC17H16O4
Net Charge0
Average Mass284.311
Monoisotopic Mass284.10486
SMILESCOc1cc(O)c(C)c(O)c1C(=O)/C=C/c1ccccc1
InChIInChI=1S/C17H16O4/c1-11-14(19)10-15(21-2)16(17(11)20)13(18)9-8-12-6-4-3-5-7-12/h3-10,19-20H,1-2H3/b9-8+
InChIKeyJUZVHLGKYJTCKP-CMDGGOBGSA-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:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) has functional parent trans-chalcone (CHEBI:48965)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) has role plant metabolite (CHEBI:76924)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) is a chalcones (CHEBI:23086)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) is a monomethoxybenzene (CHEBI:25235)
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (CHEBI:70659) is a resorcinols (CHEBI:33572)
IUPAC Name 
(2E)-1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-3-phenylprop-2-en-1-one
Synonym  Source
stercurensinChEBI
Registry NumbersSources
Reaxys:4489711Reaxys
Citations