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CHEBI:132650 - burchellin

ChEBI IDCHEBI:132650
ChEBI Nameburchellin
Stars
DefinitionA neolignan with formula C20H20O5 that is isolated from Ocotea cymbarum and Piper wallichii. It is active against a variety of parasites including T. cruzi, the vector for Chagas disease.
Last Modified15 December 2016
Submitterliuqingping
DownloadsMolfile
FormulaC20H20O5
Net Charge0
Average Mass340.375
Monoisotopic Mass340.13107
SMILESC=CC[C@@]12C=C(OC)C(=O)C=C1O[C@H](c1ccc3c(c1)OCO3)[C@H]2C
InChIInChI=1S/C20H20O5/c1-4-7-20-10-17(22-3)14(21)9-18(20)25-19(12(20)2)13-5-6-15-16(8-13)24-11-23-15/h4-6,8-10,12,19H,1,7,11H2,2-3H3/t12-,19+,20+/m1/s1
InChIKeySOLJFAQVSWXZEQ-CFGAKRJMSA-N
Species of MetaboliteComponentSourceComments
Ocotea cymbarum (ncbitaxon:1844648) - PubMed (24713267)
Piper wallichii (ncbitaxon:450288) aerial part (BTO:0001658) PubMed (20394289)
Roles Classification
Biological Roles:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
antifeedant  A substance that prevents pests from feeding.
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
ChEBI Ontology
Outgoing Relation(s)
burchellin (CHEBI:132650) has role antifeedant (CHEBI:22583)
burchellin (CHEBI:132650) has role plant metabolite (CHEBI:76924)
burchellin (CHEBI:132650) has role trypanocidal drug (CHEBI:36335)
burchellin (CHEBI:132650) is a 1-benzofurans (CHEBI:38830)
burchellin (CHEBI:132650) is a benzodioxoles (CHEBI:38298)
burchellin (CHEBI:132650) is a cyclic ketone (CHEBI:3992)
burchellin (CHEBI:132650) is a enol ether (CHEBI:47985)
burchellin (CHEBI:132650) is a enone (CHEBI:51689)
burchellin (CHEBI:132650) is a neolignan (CHEBI:25497)
burchellin (CHEBI:132650) is a olefinic compound (CHEBI:78840)
burchellin (CHEBI:132650) is a ring assembly (CHEBI:36820)
IUPAC Name 
(2S,3S,3aR)-2-(2H-1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one
Manual XrefsDatabases
C00041404KNApSAcK
Registry NumbersSources
Reaxys:1355484Reaxys
CAS:38276-59-4KNApSAcK
CAS:38276-59-4ChemIDplus
Citations