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CHEBI:66539 - syncarpamide

ChEBI IDCHEBI:66539
ChEBI Namesyncarpamide
Stars
DefinitionAn alkaloid that is the di-O-cinnamoyl derivative of 3,4-di-O-methylnorepinephrine. Isolated from Zanthoxylum syncarpum, it exhibits antiplasmodial activity.
Last Modified7 March 2018
DownloadsMolfile
FormulaC28H27NO5
Net Charge0
Average Mass457.526
Monoisotopic Mass457.18892
SMILESCOc1ccc([C@@H](CNC(=O)/C=C/c2ccccc2)OC(=O)/C=C/c2ccccc2)cc1OC
InChIInChI=1S/C28H27NO5/c1-32-24-16-15-23(19-25(24)33-2)26(34-28(31)18-14-22-11-7-4-8-12-22)20-29-27(30)17-13-21-9-5-3-6-10-21/h3-19,26H,20H2,1-2H3,(H,29,30)/b17-13+,18-14+/t26-/m1/s1
InChIKeyCUXXAUBWEIJETF-AMVLLGRPSA-N
Species of MetaboliteComponentSourceComments
Zanthoxylum syncarpum (IPNI:270795-2) stem (BTO:0001300) PubMed (14738394) Air dried Stem
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.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
syncarpamide (CHEBI:66539) has functional parent (S)-noradrenaline (CHEBI:33571)
syncarpamide (CHEBI:66539) has functional parent trans-cinnamic acid (CHEBI:35697)
syncarpamide (CHEBI:66539) has role antiplasmodial drug (CHEBI:64915)
syncarpamide (CHEBI:66539) has role metabolite (CHEBI:25212)
syncarpamide (CHEBI:66539) is a alkaloid (CHEBI:22315)
syncarpamide (CHEBI:66539) is a cinnamate ester (CHEBI:36087)
syncarpamide (CHEBI:66539) is a enamide (CHEBI:51751)
syncarpamide (CHEBI:66539) is a secondary carboxamide (CHEBI:140325)
IUPAC Name 
(1S)-1-(3,4-dimethoxyphenyl)-2-{[(2E)-3-phenylprop-2-enoyl]amino}ethyl (2E)-3-phenylprop-2-enoate
Registry NumbersSources
Reaxys:9955030Reaxys
Citations