Structure Database (LMSD)

Common Name
N-(3-oxo-tetradecanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-tetradecanoyl)-homoserine lactone
Synonyms
  • 3O-C14-HSL
LM ID
LMFA08030015
Formula
Exact Mass
Calculate m/z
325.225309
Status
Curated

Classification

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 the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn, inhibits biofilm formation.4,5

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sinorhizobium meliloti (#382)
Alphaproteobacteria (#28211)
Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-acyl homoserine lactones.,
J Bacteriol, 2002
Pubmed ID: 12270827

String Representations

InChiKey (Click to copy)
YQFJJDSGBAAUPW-INIZCTEOSA-N
InChi (Click to copy)
InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCC

Other Databases

CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 345.84
Topological Polar Surface Area 74.54
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 3.87
Molar Refractivity 89.98

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Updated at
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