Structure Database (LMSD)

Common Name
N-tetradecanoyl-homoserine lactone
Systematic Name
N-tetradecanoyl-homoserine lactone
Synonyms
  • C14:0-HSL
  • C14-HSL
LM ID
LMFA08030038
Formula
C18H33NO3
Exact Mass
Calculate m/z
311.246044
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Fatty acyl homoserine lactones [FA0803]

Biological Context

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-tetradecanoyl-L-Homoserine lactone (C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 It appears later than shorter acyl chain AHLs in developing biofilms4 and, like other long chain AHLs, stimulates bacterial growth.5 C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.6

This information has been provided by Cayman Chemical

References

1. Kuo, A., Blough, N.V., and Dunlap, P.V. Multiple N-acyl-ʟ-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri. J. Bacteriol. 176(24), 7558-7565 (1994).
2. Lithgow, J.K., Wilkinson, A., Hardman, A., et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci. Mol. Microbiol. 37(1), 81-97 (2000).
3. McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 143(Pt 12), 3703-3711 (1997).
4. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J. 3(3), 296-304 (2008).
5. Huang, J.J., Han, J.I., Zhang, L.H., et al. Utilization of acyl-homoserine lactone quorum signals for growth by a soil pseudomonad and Pseudomonas aeruginosa PAO1. Appl. Environ. Microbiol. 69(10), 5941-5949 (2003).
6. Stankowska, D., Kwinkowski, M., and Kaca, W. Quantification of Proteus mirabilis virulence factors and modulation by acylated homoserine lactones. J. Microbiol. Immunol. Infect. 41(3), 243-253 (2008).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Vibrio mediterranei (#689)
Gammaproteobacteria (#1236)
Genetic diversity and phenotypic plasticity of AHL-mediated Quorum sensing in environmental strains of Vibrio mediterranei.,
ISME J, 2019
Pubmed ID: 30116040

String Representations

InChiKey (Click to copy)
ZQAYHOXXVBVXPZ-INIZCTEOSA-N
InChi (Click to copy)
InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCCCCCCCCCC

Other Databases

PubChem CID
58122267
Cayman ID
10011200

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 339.69
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 4.69
Molar Refractivity 89.59

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Created at
2nd Jul 2019
Updated at
2nd Jul 2019