CHEBI:55474 - N-acyl-L-homoserine lactone

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ChEBI Name N-acyl-L-homoserine lactone
ChEBI ID CHEBI:55474
ChEBI ASCII Name N-acyl-L-homoserine lactone
Definition An N-acyl homoserine lactone that has L configuration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H6NO3R
Net Charge 0
Average Mass (excl. R groups) 128.106
Monoisotopic Mass (excl. R groups) 128.03477
SMILES O1C([C@H](CC1)NC(=O)*)=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 )
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ChEBI Ontology
Outgoing N-acyl-L-homoserine lactone (CHEBI:55474) has functional parent L-homoserine lactone (CHEBI:30655)
N-acyl-L-homoserine lactone (CHEBI:55474) is a N-acyl homoserine lactone (CHEBI:83169)
Incoming N-(3-oxododecanoyl)-L-homoserine lactone (CHEBI:44534) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-(3-oxohexanoyl)-L-homoserine lactone (CHEBI:63789) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-(4-coumaroyl)-L-homoserine lactone (CHEBI:74974) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-(8-carboxy-3-oxooctanoyl)-L-homoserine lactone (CHEBI:63226) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-butyryl-L-homoserine lactone (CHEBI:29643) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-dodecanoyl-L-homoserine lactone (CHEBI:55555) is a N-acyl-L-homoserine lactone (CHEBI:55474)
N-isovaleryl-L-homoserine lactone (CHEBI:74958) is a N-acyl-L-homoserine lactone (CHEBI:55474)
IUPAC Name
(3S)-3-alkanamido-4,5-dihydrofuran-2(3H)-one
Synonyms Sources
AHL ChEBI
AHLs ChEBI
an N-acyl-L-homoserine lactone UniProt
N-acyl-L-homoserine lactones ChEBI
N-acyl-S-homoserine lactone ChEBI
N-acyl-S-homoserine lactones ChEBI
N-AHL ChEBI
N-AHLs ChEBI
Manual Xref Database
C18049 KEGG COMPOUND
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Citations Waiting for Citations Types Sources
10794136 PubMed citation Europe PMC
17338438 PubMed citation Europe PMC
Last Modified
05 September 2017
General Comment
2011-01-27 A class of autoinducers (small diffusible signal molecules which coordinate gene expression), each of which generally consists of a fatty acid coupled with homoserine lactone (HSL).