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CHEBI:65630 - ciliatamide A

ChEBI IDCHEBI:65630
ChEBI Nameciliatamide A
Stars
DefinitionA lipopeptide that contains N-methylphenylalanine and lysine as the amino acid residues linked to a dec-9-enoyl moiety via an amide linkage (the R,R stereoisomer). It is isolated from the deep sea sponge Aaptos ciliata and exhibits antileishmanial activity.
Last Modified11 December 2012
DownloadsMolfile
FormulaC26H39N3O3
Net Charge0
Average Mass441.616
Monoisotopic Mass441.29914
SMILESC=CCCCCCCCC(=O)N(C)[C@H](Cc1ccccc1)C(=O)N[C@@H]1CCCCNC1=O
InChIInChI=1S/C26H39N3O3/c1-3-4-5-6-7-8-12-18-24(30)29(2)23(20-21-15-10-9-11-16-21)26(32)28-22-17-13-14-19-27-25(22)31/h3,9-11,15-16,22-23H,1,4-8,12-14,17-20H2,2H3,(H,27,31)(H,28,32)/t22-,23-/m1/s1
InChIKeyUNVIKJZRLTXMOH-DHIUTWEWSA-N
Species of MetaboliteComponentSourceComments
Aaptos ciliata (WORMS:170732) - PubMed (18257536)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
Application:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
ChEBI Ontology
Outgoing Relation(s)
ciliatamide A (CHEBI:65630) has functional parent dec-9-enoic acid (CHEBI:32381)
ciliatamide A (CHEBI:65630) has role antileishmanial agent (CHEBI:70868)
ciliatamide A (CHEBI:65630) has role metabolite (CHEBI:25212)
ciliatamide A (CHEBI:65630) is a caprolactams (CHEBI:23000)
ciliatamide A (CHEBI:65630) is a lipopeptide (CHEBI:46895)
IUPAC Name 
N-methyl-N-[(2R)-1-oxo-1-{[(3R)-2-oxoazepan-3-yl]amino}-3-phenylpropan-2-yl]dec-9-enamide
Synonym  Source
(R,R)-ciliatamide AChEBI
Registry NumbersSources
Reaxys:19040133Reaxys
Citations