Structure Database (LMSD)
Common Name
N-(dodecanoyl)-homoserine lactone
Systematic Name
N-(dodecanoyl)-homoserine lactone
Synonyms
- C12-HSL
3D model of N-(dodecanoyl)-homoserine lactone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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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Updated at
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