CHEBI:70664 - (2S)-5,7-dihydroxy-6,8-dimethylflavanone

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ChEBI Name (2S)-5,7-dihydroxy-6,8-dimethylflavanone
ChEBI ID CHEBI:70664
ChEBI ASCII Name (2S)-5,7-dihydroxy-6,8-dimethylflavanone
Definition A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 7 and methyl groups at positions 6 and 8. 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 C17H16O4
Net Charge 0
Average Mass 284.30650
Monoisotopic Mass 284.10486
InChI InChI=1S/C17H16O4/c1-9-15(19)10(2)17-14(16(9)20)12(18)8-13(21-17)11-6-4-3-5-7-11/h3-7,13,19-20H,8H2,1-2H3/t13-/m0/s1
InChIKey HAIHGFWQOPJMPV-ZDUSSCGKSA-N
SMILES Cc1c(O)c(C)c2O[C@@H](CC(=O)c2c1O)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): 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.
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ChEBI Ontology
Outgoing (2S)-5,7-dihydroxy-6,8-dimethylflavanone (CHEBI:70664) has functional parent (2S)-flavanone (CHEBI:15606)
(2S)-5,7-dihydroxy-6,8-dimethylflavanone (CHEBI:70664) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
(2S)-5,7-dihydroxy-6,8-dimethylflavanone (CHEBI:70664) has role plant metabolite (CHEBI:76924)
(2S)-5,7-dihydroxy-6,8-dimethylflavanone (CHEBI:70664) is a dihydroxyflavanone (CHEBI:38749)
IUPAC Name
(2S)-5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4H-chromen-4-one
Synonyms Sources
(−)-demethoxymatteucinol ChemIDplus
(2S)-2,3-dihydro-5,7-dihydroxy-6,8-dimethyl-2-phenyl-4H-1-benzopyran-4-one ChemIDplus
6,8-dimethylpinocembrin ChemIDplus
demethoxymatteucinol ChEBI
Registry Numbers Types Sources
1290952 Reaxys Registry Number Reaxys
56297-79-1 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
20886838 PubMed citation Europe PMC
Last Modified
01 October 2014