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CHEBI:66460 - selinone

ChEBI IDCHEBI:66460
ChEBI Nameselinone
Stars
DefinitionA dihydroxyflavanone that is 5,7-dihydroxyflavanone substituted by a prenyloxy group at position 4' (the 2S stereoisomer). Isolated from Selinum vaginatum and Monotes engleri, it exhibits antifungal activity.
Last Modified9 April 2018
DownloadsMolfile
FormulaC20H20O5
Net Charge0
Average Mass340.375
Monoisotopic Mass340.13107
SMILESCC(C)=CCOc1ccc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc1
InChIInChI=1S/C20H20O5/c1-12(2)7-8-24-15-5-3-13(4-6-15)18-11-17(23)20-16(22)9-14(21)10-19(20)25-18/h3-7,9-10,18,21-22H,8,11H2,1-2H3/t18-/m0/s1
InChIKeyGYSDUVRPSWKYDJ-SFHVURJKSA-N
Species of MetaboliteComponentSourceComments
Selinum vaginatum (ncbitaxon:239673) - DOI (10.1016/S0040-4039(00)71577-2)
Monotes engleri (IPNI:321075-1) leaf (BTO:0000713) DOI (10.1002/hlca.19980810325)
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.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ChEBI Ontology
Outgoing Relation(s)
selinone (CHEBI:66460) has functional parent (S)-naringenin (CHEBI:17846)
selinone (CHEBI:66460) has role antifungal agent (CHEBI:35718)
selinone (CHEBI:66460) has role plant metabolite (CHEBI:76924)
selinone (CHEBI:66460) is a (2S)-flavan-4-one (CHEBI:140377)
selinone (CHEBI:66460) is a aromatic ether (CHEBI:35618)
selinone (CHEBI:66460) is a dihydroxyflavanone (CHEBI:38749)
IUPAC Name 
(2S)-5,7-dihydroxy-2-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-2,3-dihydro-4H-chromen-4-one
Synonyms  Source
4'-O-prenylnaringeninHMDB
5,7-dihydroxy-4'-prenyloxyflavanoneChEBI
archangeloneHMDB
Manual XrefsDatabases
LMPK12140278LIPID MAPS
HMDB0037585HMDB
Registry NumbersSources
Reaxys:20282948Reaxys
CAS:14117-54-5ChemIDplus
Citations