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CHEBI:65709 - cylindol A

ChEBI IDCHEBI:65709
ChEBI Namecylindol A
Stars
DefinitionA benzoate ester that is methyl 4-hydroxybenzoate bearing a 2-hydroxy-5-(methoxycarbonyl)phenoxy group at position 3. It is isolated from the rhizomes of Imperata cylindrica and has been found to exhibit inhibitory activity against 5-lipoxygenase.
Last Modified11 March 2015
DownloadsMolfile
FormulaC16H14O7
Net Charge0
Average Mass318.281
Monoisotopic Mass318.07395
SMILESCOC(=O)c1ccc(O)c(Oc2cc(C(=O)OC)ccc2O)c1
InChIInChI=1S/C16H14O7/c1-21-15(19)9-3-5-11(17)13(7-9)23-14-8-10(16(20)22-2)4-6-12(14)18/h3-8,17-18H,1-2H3
InChIKeyOEYSNLOOZVNLRA-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Imperata cylindrica (ncbitaxon:80369) rhizome (BTO:0001181) PubMed (7798964)
Roles Classification
Biological Roles:
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor  A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34).
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)
cylindol A (CHEBI:65709) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964)
cylindol A (CHEBI:65709) has role plant metabolite (CHEBI:76924)
cylindol A (CHEBI:65709) is a aromatic ether (CHEBI:35618)
cylindol A (CHEBI:65709) is a benzoate ester (CHEBI:36054)
cylindol A (CHEBI:65709) is a methyl ester (CHEBI:25248)
cylindol A (CHEBI:65709) is a phenols (CHEBI:33853)
IUPAC Name 
dimethyl 3,3'-oxybis(4-hydroxybenzoate)
Synonym  Source
methyl 4-hydroxy-3-(2-hydroxy-5-methoxycarbonylphenoxy)benzoateChEBI
Citations