burchellin (CHEBI:132650)

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ChEBI Name	burchellin

ChEBI ID	CHEBI:132650

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	qingping liu

Supplier Information

Download	Molfile XML SDF

Formula

C20H20O5

Net Charge

Average Mass

340.371

Monoisotopic Mass

340.13107

InChI

InChI=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

InChIKey

SOLJFAQVSWXZEQ-CFGAKRJMSA-N

SMILES

O1[C@@H]([C@H]([C@]2(C1=CC(=O)C(OC)=C2)CC=C)C)C3=CC=4OCOC4C=C3

Metabolite of Species	Details
Ocotea cymbarum (NCBI:txid1844648)	See: PubMed
Piper wallichii (NCBI:txid450288)	Found in aerial part (BTO:0001658). See: PubMed

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. trypanocidal drug A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.

Application(s):	trypanocidal drug A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida. antifeedant A substance that prevents pests from feeding.

ChEBI Ontology
Outgoing	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

Last Modified

15 December 2016