CHEBI:65630 - ciliatamide A

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ChEBI Name ciliatamide A
ChEBI ID CHEBI:65630
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H39N3O3
Net Charge 0
Average Mass 441.60620
Monoisotopic Mass 441.29914
InChI InChI=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
InChIKey UNVIKJZRLTXMOH-DHIUTWEWSA-N
SMILES CN([C@H](Cc1ccccc1)C(=O)N[C@@H]1CCCCNC1=O)C(=O)CCCCCCCC=C
Metabolite of Species Details
Aaptos ciliata (WORMS:170732) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 A ChEBI
Registry Number Type Source
19040133 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18257536 PubMed citation Europe PMC
18788742 PubMed citation Europe PMC
Last Modified
11 December 2012
General Comment
2012-12-11 The structure is based on the revised stereochemistry:Org Lett. 2008, 10(20), 4545-8.