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CHEBI:68373 - (−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone

ChEBI IDCHEBI:68373
ChEBI Name(−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone
Stars
ASCII Name(-)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone
DefinitionA trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 2', a prenyl group at position 8 and a dimethylallyl group at position 5'. Isolated from Dalea boliviana, it exhibits inhibitory activity against tyrosinase.
Last Modified25 March 2015
DownloadsMolfile
FormulaC25H28O5
Net Charge0
Average Mass408.494
Monoisotopic Mass408.19367
SMILESC=CC(C)(C)c1ccc(O)c([C@@H]2CC(=O)c3c(O)cc(O)c(CC=C(C)C)c3O2)c1
InChIInChI=1S/C25H28O5/c1-6-25(4,5)15-8-10-18(26)17(11-15)22-13-21(29)23-20(28)12-19(27)16(24(23)30-22)9-7-14(2)3/h6-8,10-12,22,26-28H,1,9,13H2,2-5H3/t22-/m0/s1
InChIKeyXTXBYTLPTUGDBR-QFIPXVFZSA-N
Species of MetaboliteComponentSourceComments
Dalea boliviana (IPNI:76040-2) root (BTO:0001188) PubMed (21226489) n-hexane extract of dried, powdered roots
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 1.14.18.1 (tyrosinase) inhibitor  Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
ChEBI Ontology
Outgoing Relation(s)
(−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone (CHEBI:68373) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
(−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone (CHEBI:68373) has role plant metabolite (CHEBI:76924)
(−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone (CHEBI:68373) is a trihydroxyflavanone (CHEBI:38739)
IUPAC Name 
(2S)-5,7-dihydroxy-2-[2-hydroxy-5-(2-methylbut-3-en-2-yl)phenyl]-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
Registry NumbersSources
Reaxys:21306689Reaxys
Citations