ciliatamide B

CHEBI:65631 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:23000 CHEBI:23000
CHEBI:46895 CHEBI:46895

Chemical structure

Computed structure properties
Molecular formula	C24H37N3O3
Charge	0
Average mass	415.578 Da
Monoisotopic mass	415.28349 Da
Source	ChEBI
InChIKey	FNPKNWJUFWGJJV-NHCUHLMSSA-N

SMILES

CCCCCCCC(=O)N(C)[C@H](Cc1ccccc1)C(=O)N[C@@H]1CCCCNC1=O

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

Also called

Nα-methyl-Nα-octanoyl-N-[(3R)-2-oxoazepan-3-yl]-D-phenylalaninamide (EXACT_SYNONYM)— chebi
(R,R)-ciliatamide B (EXACT_SYNONYM)— chebi
N-methyl-N-[(2R)-1-oxo-1-[[(3R)-2-oxoazepan-3-yl]amino]-3-phenylpropan-2-yl]octanamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:19040123

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:70868 CHEBI:70868

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:65631`	ciliatamide B	`antibioticmech:chebi-5bee97b306`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.