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

Default Structure
ChEBI IDCHEBI:29640
ChEBI NameN-(3-oxohexanoyl)homoserine lactone
Stars
ASCII NameN-(3-oxohexanoyl)homoserine lactone
DefinitionA 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.
Last Modified2 July 2018
DownloadsMolfile
FormulaC10H15NO4
Net Charge0
Average Mass213.233
Monoisotopic Mass213.10011
SMILESCCCC(=O)CC(=O)NC1CCOC1=O
InChIInChI=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)
InChIKeyYRYOXRMDHALAFL-UHFFFAOYSA-N
Roles Classification
Biological Role:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
3-oxo-C6-AHLChEBI
3-oxo-N-(tetrahydro-2-oxo-3-furanyl)hexanamideChemIDplus
AI-1 (Vibrio fischeri)MetaCyc
AI-1 lactoneChemIDplus
Autoinducer 1ChemIDplus
N-(3-oxohexanoyl)-3-aminodihydro-2(3H)-furanoneChemIDplus
Manual XrefsDatabases
C11839KEGG COMPOUND
CPD-10780MetaCyc
Registry NumbersSources
Reaxys:13576940Reaxys
CAS:76924-95-3KEGG COMPOUND
CAS:76924-95-3ChemIDplus
Citations