CHEBI:65631 - ciliatamide B

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ChEBI Name ciliatamide B
ChEBI ID CHEBI:65631
Definition A lipopeptide that contains N-methylphenylalanine and lysine as the amino acid residues linked to a octanoyl moiety via an amide linkage (the R,R stereoisomer). It is isolated from the deep sea sponge Aaptos ciliata and exhibits antileishmanial and moderate cytotoxicity towards HeLa cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H37N3O3
Net Charge 0
Average Mass 415.56890
Monoisotopic Mass 415.28349
InChI InChI=1S/C24H37N3O3/c1-3-4-5-6-10-16-22(28)27(2)21(18-19-13-8-7-9-14-19)24(30)26-20-15-11-12-17-25-23(20)29/h7-9,13-14,20-21H,3-6,10-12,15-18H2,1-2H3,(H,25,29)(H,26,30)/t20-,21-/m1/s1
InChIKey FNPKNWJUFWGJJV-NHCUHLMSSA-N
SMILES CCCCCCCC(=O)N(C)[C@H](Cc1ccccc1)C(=O)N[C@@H]1CCCCNC1=O
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): 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(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ciliatamide B (CHEBI:65631) has functional parent octanoic acid (CHEBI:28837)
ciliatamide B (CHEBI:65631) has role antileishmanial agent (CHEBI:70868)
ciliatamide B (CHEBI:65631) has role antineoplastic agent (CHEBI:35610)
ciliatamide B (CHEBI:65631) has role metabolite (CHEBI:25212)
ciliatamide B (CHEBI:65631) is a caprolactams (CHEBI:23000)
ciliatamide B (CHEBI:65631) is a lipopeptide (CHEBI:46895)
IUPAC Name
Nα-methyl-Nα-octanoyl-N-[(3R)-2-oxoazepan-3-yl]-D-phenylalaninamide
Synonyms Sources
(R,R)-ciliatamide B ChEBI
N-methyl-N-[(2R)-1-oxo-1-[[(3R)-2-oxoazepan-3-yl]amino]-3-phenylpropan-2-yl]octanamide ChEBI
Registry Number Type Source
19040123 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.