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

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ChEBI Name (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone
ChEBI ID CHEBI:70661
ChEBI ASCII Name (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H16O5
Net Charge 0
Average Mass 312.31660
Monoisotopic Mass 312.09977
InChI InChI=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
InChIKey QJQJKEWQUOORFC-AWEZNQCLSA-N
SMILES COc1c(C)c(O)c2C(=O)C[C@H](Oc2c1C=O)c1ccccc1
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): 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(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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 Number Type Source
10367824 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
20886838 PubMed citation Europe PMC
Last Modified
01 October 2014