CHEBI:66539 - syncarpamide

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ChEBI Name syncarpamide
ChEBI ID CHEBI:66539
Definition An alkaloid that is the di-O-cinnamoyl derivative of 3,4-di-O-methylnorepinephrine. Isolated from Zanthoxylum syncarpum, it exhibits antiplasmodial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H27NO5
Net Charge 0
Average Mass 457.51770
Monoisotopic Mass 457.18892
InChI InChI=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
InChIKey CUXXAUBWEIJETF-AMVLLGRPSA-N
SMILES COc1ccc(cc1OC)[C@@H](CNC(=O)\C=C\c1ccccc1)OC(=O)\C=C\c1ccccc1
Metabolite of Species Details
Zanthoxylum syncarpum (IPNI:270795-2) Found in stem (BTO:0001300). Air dried Stem See: PubMed
Roles Classification
Biological Role(s): 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.
(via alkaloid )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Number Type Source
9955030 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
14738394 PubMed citation Europe PMC
Last Modified
07 March 2018