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CHEBI:70661 - (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone

ChEBI IDCHEBI:70661
ChEBI Name(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone
Stars
ASCII Name(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone
DefinitionA monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5, a methoxy group at position 7, a methyl group at position 6 and a formyl group at position 8. Isolated from 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
FormulaC18H16O5
Net Charge0
Average Mass312.321
Monoisotopic Mass312.09977
SMILESCOc1c(C)c(O)c2c(c1C=O)O[C@H](c1ccccc1)CC2=O
InChIInChI=1S/C18H16O5/c1-10-16(21)15-13(20)8-14(11-6-4-3-5-7-11)23-18(15)12(9-19)17(10)22-2/h3-7,9,14,21H,8H2,1-2H3/t14-/m0/s1
InChIKeyQJQJKEWQUOORFC-AWEZNQCLSA-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)
(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (CHEBI:70661) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (CHEBI:70661) has role plant metabolite (CHEBI:76924)
(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (CHEBI:70661) is a aldehyde (CHEBI:17478)
(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (CHEBI:70661) is a monohydroxyflavanone (CHEBI:38748)
(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone (CHEBI:70661) is a monomethoxyflavanone (CHEBI:38738)
IUPAC Name 
(2S)-5-hydroxy-7-methoxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-chromene-8-carbaldehyde
Registry NumbersSources
Reaxys:10367824Reaxys
Citations