Structure Database (LMSD)

Common Name
N-decanoyl-homoserine lactone
Systematic Name
N-decanoyl-homoserine lactone
Synonyms
  • C10:0-HSL
LM ID
LMFA08030026
Formula
C14H25NO3
Exact Mass
Calculate m/z
255.183444
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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

N-decanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism.1 The applications of this molecule include regulation of virulence and exoproteases.2

This information has been provided by Cayman Chemical

References

1. Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 153 (Pt 12), 3923-3938 (2007).
2. Barnard, A.M.L., and Salmond, G.P.C. Quorum sensing: The complexities of chemical communication between bacteria. Complexus 5(2), 87-101 (2004).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue,
Appl Environ Microbiol, 2007
Pubmed ID: 17085703

String Representations

InChiKey (Click to copy)
TZWZKDULKILUPV-LBPRGKRZSA-N
InChi (Click to copy)
InChI=1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)/t12-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CCCCCCCCC

Other Databases

CHEBI ID
190815
PubChem CID
10131281
Cayman ID
10011201
PDB ID
HL0

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 270.49
Topological Polar Surface Area 57.47
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 3.13
Molar Refractivity 71.12

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