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

ChEBI IDCHEBI:70653
ChEBI Name(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone
Stars
ASCII Name(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone
DefinitionA 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.
Last Modified6 February 2018
DownloadsMolfile
FormulaC17H16O5
Net Charge0
Average Mass300.310
Monoisotopic Mass300.09977
SMILESCc1c(O)c(C)c2c(c1O)C(=O)[C@@H](O)[C@H](c1ccccc1)O2
InChIInChI=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
InChIKeyHDEMWSJTNCFIGR-WBVHZDCISA-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,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-dimethyldihydroflavonolChEBI
Citations