CHEBI:70653 - (2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone

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ChEBI Name (2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone
ChEBI ID CHEBI:70653
ChEBI ASCII Name (2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone
Definition A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 3, 5 and 7 and methyl groups at positions 6 and 8 (the 2S,3S-stereoisomer). It has been isolated from the buds of Cleistocalyx operculatus and 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 C17H16O5
Net Charge 0
Average Mass 300.30590
Monoisotopic Mass 300.09977
InChI InChI=1S/C17H16O5/c1-8-12(18)9(2)16-11(13(8)19)14(20)15(21)17(22-16)10-6-4-3-5-7-10/h3-7,15,17-19,21H,1-2H3/t15-,17+/m1/s1
InChIKey HDEMWSJTNCFIGR-WBVHZDCISA-N
SMILES Cc1c(O)c(C)c2O[C@H]([C@H](O)C(=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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone (CHEBI:70653) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone (CHEBI:70653) has role plant metabolite (CHEBI:76924)
(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone (CHEBI:70653) is a dihydroflavonols (CHEBI:48039)
(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone (CHEBI:70653) is a secondary α-hydroxy ketone (CHEBI:2468)
(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone (CHEBI:70653) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name
(2S,3S)-3,5,7-trihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4H-chromen-4-one
Synonym Source
(2S,3S)-2,3-trans-5,7-dihydroxy-6,8-dimethyldihydroflavonol ChEBI
Citation Waiting for Citations Type Source
20886838 PubMed citation Europe PMC
Last Modified
06 February 2018