Structure Database (LMSD)

Common Name
N-octanoyl-homoserine lactone
Systematic Name
N-octanoyl-homoserine lactone
Synonyms
  • C8-HSL
LM ID
LMFA08030035
Formula
C12H21NO3
Exact Mass
Calculate m/z
227.152144
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

N-octanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism.1,2,3 The applications of this molecule include infection prevention and regulation of virulence in general and in cystic fibrosis.4,5

This information has been provided by Cayman Chemical

References

1. Winson, M.K., Camara, M., Latifi, A., et al. Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 92(20), 9427-9431 (1995).
2. 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).
3. Riedel, K., Hentzer, M., Geisenberger, O., et al. N-acylhomoserine-lactone-mediated communication between Pseudomonas aeruginosa and Burkholderia cepacia in mixed biofilms. Microbiology 147(Pt 12), 3249-3262 (2001).
4. 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).
5. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue,
Appl Environ Microbiol, 2007
Pubmed ID: 17085703

String Representations

InChiKey (Click to copy)
JKEJEOJPJVRHMQ-JTQLQIEISA-N
InChi (Click to copy)
InChI=1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCCCC

Other Databases

CHEBI ID
195581
PubChem CID
6914579
Cayman ID
10011199
PDB ID
HTF
GuidePharm ID
12447

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 1
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 235.89
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 2.35
Molar Refractivity 61.88

Admin

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