Structure Database (LMSD)

Common Name
N-hexanoyl-homoserine lactone
Systematic Name
N-hexanoyl-homoserine lactone
Synonyms
  • C6:0-HSL
LM ID
LMFA08030025
Formula
Exact Mass
Calculate m/z
199.120844
Status
Curated


Classification

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
Pubmed ID: 26729121

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

CHEBI ID
PubChem CID
Cayman ID
PDB ID

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

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Created at
1st Jul 2019
Updated at
1st Jul 2019