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CHEBI:6116 - kavapyrone

ChEBI IDCHEBI:6116
ChEBI Namekavapyrone
Stars
DefinitionA pyranone that is 2H-pyran-2-one substituted by a methoxy group at position 4 and a 3-phenyloxiran-2-yl group at position 6 (the 2R,3S stereoisomer). Isolated from Didymocarpus aurantiacus and Piper rusbyi, it exhibits antileishmanial activity.
Secondary ChEBI IDCHEBI:66141
Last Modified11 May 2016
DownloadsMolfile
FormulaC14H12O4
Net Charge0
Average Mass244.246
Monoisotopic Mass244.07356
SMILESCOc1cc([C@@H]2O[C@H]2c2ccccc2)oc(=O)c1
InChIInChI=1S/C14H12O4/c1-16-10-7-11(17-12(15)8-10)14-13(18-14)9-5-3-2-4-6-9/h2-8,13-14H,1H3/t13-,14-/m0/s1
InChIKeyMLGUXXSGWWCJQW-KBPBESRZSA-N
Species of MetaboliteComponentSourceComments
Piper rusbyi (ncbitaxon:538341) leaf (BTO:0000713) PubMed (17354169)
Didymocarpus aurantiacus (IPNI:380332-1) - Article (INDIAN J CHEM SEC B, 1976, 14, 909)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
Application:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
ChEBI Ontology
Outgoing Relation(s)
kavapyrone (CHEBI:6116) has role antileishmanial agent (CHEBI:70868)
kavapyrone (CHEBI:6116) has role metabolite (CHEBI:25212)
kavapyrone (CHEBI:6116) is a 2-pyranones (CHEBI:75885)
kavapyrone (CHEBI:6116) is a epoxide (CHEBI:32955)
kavapyrone (CHEBI:6116) is a ether (CHEBI:25698)
IUPAC Name 
4-methoxy-6-[(2R,3S)-3-phenyloxiran-2-yl]-2H-pyran-2-one
Synonym  Source
(+)-(7R,8S)-epoxy-5,6-didehydrokavainChEBI
Registry NumbersSources
Reaxys:11152408Reaxys
Citations