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

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ChEBI Name (−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone
ChEBI ASCII Name (-)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H26O5
Net Charge 0
Average Mass 406.47090
Monoisotopic Mass 406.17802
InChI InChI=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
SMILES CC(C)=CCc1cccc([C@@H]2CC(=O)c3c(O)cc4OC(C)(C)C=Cc4c3O2)c1O
Metabolite of Species Details
Dalea boliviana (IPNI:76040-2) Found in root (BTO:0001188). n-hexane extract of dried, powdered roots See: PubMed
Roles Classification
Biological Role(s): EC (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, 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-(2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2'',3'')-3'-prenylflavanone (CHEBI:68375) has role EC (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)
Registry Number Type Source
21306688 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21226489 PubMed citation Europe PMC
Last Modified
25 March 2015