Structure Database (LMSD)
Common Name
N-hexanoyl-homoserine lactone
Systematic Name
N-hexanoyl-homoserine lactone
Synonyms
- C6:0-HSL
3D model of N-hexanoyl-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. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-hexanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism.1 The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.2,3,4,5,6,7,8
This information has been provided by Cayman Chemical
References
1. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J. Bacteriol. 188(2), 773-783 (2006).
3. Ulrich, R.L., Hines, H.B., Parthasarathy, N., et al. Mutational analysis and biochemical characterization of the bukholderia thailandensis DW503 quorum-sensing network. J. Bacteriol. 186(13), 4350-4360 (2004).
4. Wang, L.H., Weng, L.X., Dong, Y.H., et al. Specificity and enzyme kinetics of the quorum-quenching N-acyl homoserine lactone lactonase (AHL-lactonase). The Journal of Biological Chemisty 279(14), 13645-13651 (2004).
6. Luo, Z.Q., Su, S., and Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J. Bacteriol. 186(19), 5665-5672 (2003).
7. Christensen, A.B., Riedel, K., Eberl, L., et al. Quorum-sensing-directed protein expression in Serratia proteamaculans B5a. Microbiology 149(Pt 2), 471-483 (2003).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Bosea massiliensis
(#151419)
Alphaproteobacteria
(#28211)
Characterization of N-Acylhomoserine Lactones Produced by Bacteria Isolated from Industrial Cooling Water Systems.,
Sensors (Basel), 2015
Sensors (Basel), 2015
Pubmed ID:
26729121
DOI:
10.3390/s16010044
String Representations
InChiKey (Click to copy)
ZJFKKPDLNLCPNP-QMMMGPOBSA-N
InChi (Click to copy)
InChI=1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)/t8-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
14
Rings
1
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
201.29
Topological Polar Surface Area
57.47
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
4
logP
1.57
Molar Refractivity
52.65
Admin
Created at
1st Jul 2019
Updated at
1st Jul 2019