Structure Database (LMSD)

Common Name
N-(hexadecanoyl)-homoserine lactone
Systematic Name
N-(hexadecanoyl)-homoserine lactone
Synonyms
  • C16-HSL
LM ID
LMFA08030012
Formula
Exact Mass
Calculate m/z
339.277344
Status
Curated

Classification

Biological Context

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.2 Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases.3 AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family.4 C16-HSL is one of a number of lipophilic, long acyl side-chain bearing AHLs, including its monounsaturated analog C16:1-(L)-HSL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes.5,6 C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells.7 N-Hexadecanoyl-L-homoserine lactone and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.8,9

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).
7. Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes. Mol. Microbiol. 61(4), 839-846 (2006).
8. Schaefer, A.L., Taylor, T.A., Beatty, J.T., et al. Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production. J. Bacteriol. 184(23), 6515-6521 (2002).
9. Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals. J. Bacteriol. 181(4), 1203-1210 (1999).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rhodovulum sulfidophilum (#35806)
Alphaproteobacteria (#28211)
Identification of novel long chain N-acylhomoserine lactones of chain length C20 from the marine phototrophic bacterium Rhodovulum sulfidophilum.,
Biosci Biotechnol Biochem, 2018
Pubmed ID: 30001674

String Representations

InChiKey (Click to copy)
QJIXVOQAEZMUIH-SFHVURJKSA-N
InChi (Click to copy)
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h18H,2-17H2,1H3,(H,21,22)/t18-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCCCCCCCCCCCC

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 374.29
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 5.47
Molar Refractivity 98.82

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Updated at
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