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CHEBI:68375 - (−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone

ChEBI IDCHEBI:68375
ChEBI Name(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone
Stars
ASCII Name(-)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone
DefinitionAn extended flavonoid that is (2S)-flavanone substituted b y hydroxy groups at positions 5 and 2', prenyl group at position 3 and a gem-dimethylpyran ring fused across positions 7 and 8. Isolated from Dalea boliviana, it exhibits inhibitory activity against tyrosinase.
Last Modified25 March 2015
DownloadsMolfile
FormulaC25H26O5
Net Charge0
Average Mass406.478
Monoisotopic Mass406.17802
SMILESCC(C)=CCc1cccc([C@@H]2CC(=O)c3c(O)cc4c(c3O2)C=CC(C)(C)O4)c1O
InChIInChI=1S/C25H26O5/c1-14(2)8-9-15-6-5-7-16(23(15)28)20-12-18(26)22-19(27)13-21-17(24(22)29-20)10-11-25(3,4)30-21/h5-8,10-11,13,20,27-28H,9,12H2,1-4H3/t20-/m0/s1
InChIKeyVPMGXHDHUFGBBL-FQEVSTJZSA-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:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) has role plant metabolite (CHEBI:76924)
(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) is a dihydroxyflavanone (CHEBI:38749)
(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) is a extended flavonoid (CHEBI:71037)
(−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(2S)-5-hydroxy-2-[2-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
Registry NumbersSources
Reaxys:21306688Reaxys
Citations