Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 00:14:37 UTC
Update Date2025-10-07 16:05:15 UTC
Metabolite IDMMDBc0006864
Metabolite Identification
Common NameN-decanoyl-L-homoserine lactone
DescriptionN-decanoyl-L-homoserine lactone is a member of the N-acyl homoserine lactone (AHL) chemical class, which functions as a quorum-sensing molecule in various bacterial species. This metabolite plays a crucial role in cell-cell communication, influencing behaviors such as biofilm formation and gene regulation. For instance, it has been shown to affect copper-induced conjugative transfer of antibiotic resistance genes (PMID:40840413 ) and to upregulate functional genes involved in polyvinyl alcohol degradation in Geotrichum when sensed by Acidovorax (PMID:40184710 ). Additionally, N-decanoyl-L-homoserine lactone has been implicated in inhibiting primary root growth in Arabidopsis, although the underlying mechanisms remain unclear (PMID:36229795 ). It is also involved in the activation of biosynthetic gene clusters in symbiotic bacteria, highlighting its importance in symbiotic relationships (PMID:35611654 ). Furthermore, its concentrations in biofilms have been found to correlate with the abundance of immigrant bacteria, suggesting its role in microbial community dynamics (PMID:34289594 ). Overall, N-decanoyl-L-homoserine lactone exemplifies the intricate interplay between microbial metabolites and biological processes.
Structure
SynonymsNot Available
Molecular FormulaC14H25NO3
Average Mass255.3532
Monoisotopic Mass255.183443671
IUPAC NameN-[(3S)-2-oxooxolan-3-yl]decanimidic acid
Traditional NameN-[(3S)-2-oxooxolan-3-yl]decanimidic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CCOC1=O)N=C(O)CCCCCCCCC
InChI Identifier
InChI=1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)/t12-/m0/s1
InChI KeyTZWZKDULKILUPV-LBPRGKRZSA-N