CHEBI:65642 - 8'-epi-cleomiscosin A

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ChEBI Name 8'-epi-cleomiscosin A
ChEBI ASCII Name 8'-epi-cleomiscosin A
Definition An organic heterotricyclic compound that is 2,3-dihydro-9H-[1,4]dioxino[2,3-h]chromen-9-one substituted by 4-hydroxy-3-methoxy phenyl group at position 3, a hydroxymethyl group at position 2 and a methoxy group at position 5 (the 2S,3R stereoisomer). An epimer of cleomiscosin A, it is isolated from the aerial parts of Rhododendron collettianum and exhibits inhibitory activity towards the enzyme tyrosinase.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H18O8
Net Charge 0
Average Mass 386.35210
Monoisotopic Mass 386.10017
InChI InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17+/m0/s1
SMILES [H][C@@]1(Oc2c(OC)cc3ccc(=O)oc3c2O[C@H]1CO)c1ccc(O)c(OC)c1
Metabolite of Species Details
Rhododendron collettianum (IPNI:332217-1) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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ChEBI Ontology
Outgoing 8'-epi-cleomiscosin A (CHEBI:65642) has role EC (tyrosinase) inhibitor (CHEBI:59997)
8'-epi-cleomiscosin A (CHEBI:65642) has role metabolite (CHEBI:25212)
8'-epi-cleomiscosin A (CHEBI:65642) is a δ-lactone (CHEBI:18946)
8'-epi-cleomiscosin A (CHEBI:65642) is a aromatic ether (CHEBI:35618)
8'-epi-cleomiscosin A (CHEBI:65642) is a organic heterotricyclic compound (CHEBI:26979)
8'-epi-cleomiscosin A (CHEBI:65642) is a phenols (CHEBI:33853)
8'-epi-cleomiscosin A (CHEBI:65642) is a primary alcohol (CHEBI:15734)
Registry Number Type Source
7114717 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15577244 PubMed citation Europe PMC
Last Modified
22 February 2013