Structure Database (LMSD)

Common Name
N-butanoyl-l-homoserine lactone
Systematic Name
N-butanoyl-l-homoserine lactone
Synonyms
  • N-Butyrylhomoserine lactone
  • C4:0-HSL
LM ID
LMFA08030002
Formula
C8H13NO3
Exact Mass
Calculate m/z
171.089544
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Fatty acyl homoserine lactones [FA0803]

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 LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-butyryl-L-Homoserine lactone is a quorum-sensing signaling molecule produced by P. aeruginosa.1 It induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 µM.2 N-butyryl-L-Homoserine lactone (50 µM) induces rhamnolipid accumulation in P. aeruginosa growth media.3

This information has been provided by Cayman Chemical

References

1. Ikeda, T., Kajiyama, K., Kita, T., et al. The synthesis of optically pure enantiomers of N-acyl-homoserine lactone autoinducers and their analogues. Chem. Lett. 30(4), 314-315 (2001).
2. Pearson, J.P., Passador, L., Igleweski, B.H., et al. A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 92(5), 1490-1494 (1995).
3. Schooling, S.R., Charaf, U.K., Allison, D.G., et al. A role for rhamnolipid in biofilm dispersion. Biofilm 1(2), 91-99 (2004).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pseudomonas aeruginosa (#287)
Gammaproteobacteria (#1236)
A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa,
Proc Natl Acad Sci U S A., 1995
Pubmed ID: 7878006

String Representations

InChiKey (Click to copy)
VFFNZZXXTGXBOG-LURJTMIESA-N
InChi (Click to copy)
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCC

Other Databases

KEGG ID
C11837
CHEBI ID
177513
PubChem CID
443433
Cayman ID
10007898
PDB ID
HL4

Calculated Physicochemical Properties

Heavy Atoms 12
Rings 1
Aromatic Rings
Rotatable Bonds 3
Van der Waals Molecular Volume 166.69
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 0.79
Molar Refractivity 43.42

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Created at
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Updated at
2nd Aug 2021