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

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ChEBI Name (−)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone
ChEBI ID CHEBI:68373
ChEBI ASCII Name (-)-(2S)-5,7,2'-trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenylflavanone
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H28O5
Net Charge 0
Average Mass 408.48680
Monoisotopic Mass 408.19367
InChI InChI=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
InChIKey XTXBYTLPTUGDBR-QFIPXVFZSA-N
SMILES CC(C)=CCc1c(O)cc(O)c2C(=O)C[C@H](Oc12)c1cc(ccc1O)C(C)(C)C=C
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 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-(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 Number Type Source
21306689 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21226489 PubMed citation Europe PMC
Last Modified
25 March 2015