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CHEBI:65642 - 8'-epi-cleomiscosin A

ChEBI IDCHEBI:65642
ChEBI Name8'-epi-cleomiscosin A
Stars
ASCII Name8'-epi-cleomiscosin A
DefinitionAn 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.
Last Modified22 February 2013
DownloadsMolfile
FormulaC20H18O8
Net Charge0
Average Mass386.356
Monoisotopic Mass386.10017
SMILES[H][C@]1(c2ccc(O)c(OC)c2)Oc2c(OC)cc3ccc(=O)oc3c2O[C@H]1CO
InChIInChI=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
InChIKeyOCBGWPJNUZMLCA-DOTOQJQBSA-N
Species of MetaboliteComponentSourceComments
Rhododendron collettianum (IPNI:332217-1) aerial part (BTO:0001658) PubMed (15577244)
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
8'-epi-cleomiscosin A (CHEBI:65642) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
8'-epi-cleomiscosin A (CHEBI:65642) has role metabolite (CHEBI:25212)
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)
8'-epi-cleomiscosin A (CHEBI:65642) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(2S,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-[1,4]dioxino[2,3-h]chromen-9-one
Registry NumbersSources
Reaxys:7114717Reaxys
Citations