Structure Database (LMSD)

Common Name
N-(dodecanoyl)-homoserine lactone
Systematic Name
N-(dodecanoyl)-homoserine lactone
Synonyms
  • C12-HSL
LM ID
LMFA08030014
Formula
Exact Mass
Calculate m/z
283.214744
Status
Curated


Classification

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-dodecanoyl-L-Homoserine lactone (C12-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β), and IL-8, while other lactones do not.4 In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells.5 It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone , which is produced at different times in biofilm development and has different cellular effects.5,6

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).
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. Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS 116(5), 361-371 (2008).
5. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sinorhizobium meliloti (#382)
Alphaproteobacteria (#28211)
Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-acyl homoserine lactones.,
J Bacteriol, 2002
Pubmed ID: 12270827

String Representations

InChiKey (Click to copy)
WILLZMOKUUPJSL-AWEZNQCLSA-N
InChi (Click to copy)
InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCCCCCCCC

Other Databases

PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 305.09
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 3.91
Molar Refractivity 80.35

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