CHEBI:29640 - N-(3-oxohexanoyl)homoserine lactone

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ChEBI Name N-(3-oxohexanoyl)homoserine lactone
ChEBI ID CHEBI:29640
ChEBI ASCII Name N-(3-oxohexanoyl)homoserine lactone
Definition A N-acyl homoserine lactone that is the monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 3-oxohexanoic acid with the amino group of homoserine lactone.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C10H15NO4
Net Charge 0
Average Mass 213.23040
Monoisotopic Mass 213.10011
InChI InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)
InChIKey YRYOXRMDHALAFL-UHFFFAOYSA-N
SMILES CCCC(=O)CC(=O)NC1CCOC1=O
Roles Classification
Biological Role(s): autoinducer
A signalling molecule produced and used by bacteria participating in quorum sensing, that is, in cell-cell communication to coordinate community-wide regulation of processes such as biofilm formation, virulence, and bioluminescence in populations of bacteria. Such communication can occur both within and between different species of bacteria.
(via N-acyl homoserine lactone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-(3-oxohexanoyl)homoserine lactone (CHEBI:29640) has functional parent 3-oxohexanoic acid (CHEBI:28422)
N-(3-oxohexanoyl)homoserine lactone (CHEBI:29640) is a N-acyl homoserine lactone (CHEBI:83169)
N-(3-oxohexanoyl)homoserine lactone (CHEBI:29640) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
3-oxo-N-(2-oxotetrahydrofuran-3-yl)hexanamide
Synonyms Sources
3-oxo-C6-AHL ChEBI
3-oxo-N-(tetrahydro-2-oxo-3-furanyl)hexanamide ChemIDplus
AI-1 (Vibrio fischeri) MetaCyc
AI-1 lactone ChemIDplus
Autoinducer 1 ChemIDplus
Luciferase autoinducer ChemIDplus
N-(3-oxohexanoyl)-3-aminodihydro-2(3H)-furanone ChemIDplus
N-(3-Oxohexanoyl)homoserine lactone KEGG COMPOUND
N-(3-oxohexanoyl)homoserine lactone ChemIDplus
N-(β-ketocapryloyl)-homoserine lactone ChEBI
Manual Xrefs Databases
C11839 KEGG COMPOUND
CPD-10780 MetaCyc
View more database links
Registry Numbers Types Sources
13576940 Reaxys Registry Number Reaxys
76924-95-3 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
7236614 PubMed citation Europe PMC
Last Modified
02 July 2018