CHEBI:6116 - kavapyrone

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ChEBI Name kavapyrone
ChEBI ID CHEBI:6116
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66141
Supplier Information
Download Molfile XML SDF
Formula C14H12O4
Net Charge 0
Average Mass 244.24270
Monoisotopic Mass 244.07356
InChI InChI=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
InChIKey MLGUXXSGWWCJQW-KBPBESRZSA-N
SMILES COc1cc(oc(=O)c1)[C@@H]1O[C@H]1c1ccccc1
Metabolite of Species Details
Didymocarpus aurantiacus (IPNI:380332-1) See: INDIAN J CHEM SEC B, 1976, 14, 909
Piper rusbyi (NCBI:txid538341) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-didehydrokavain ChEBI
Registry Number Type Source
11152408 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17354169 PubMed citation Europe PMC
Last Modified
11 May 2016
General Comment
2012-07-27 INDIAN J CHEM SEC B, 1976, 14, 909