Structure Database (LMSD)

Common Name
N-(3-oxo-pentanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-pentanoyl)-homoserine lactone
Synonyms
  • 3-oxo-C5:0-HSL
  • 3O-C5-HSL
LM ID
LMFA08030031
Formula
C9H13NO4
Exact Mass
Calculate m/z
199.084459
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

N-3-oxo-pentanoyl-L-Homoserine lactone is a chain-shortened derivative of the bacterial quorum sensing signaling molecule N-3-oxo-octanoyl-L-homoserine lactone .1 It inhibits binding of the autoinducer N-3-oxo-hexanoyl homoserine lactone to E. coli containing the transcription factor LuxR when used at a concentration of 230 nM.2 It acts as an autoinducer to activate the V. fischeri luminescence system in E. coli when used at concentrations ranging from 20 to 200 nM.

This information has been provided by Cayman Chemical

References

1. Chhabra, S.R., Stead, P., Bainton, N.J., et al. Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone. J. Antibiot. (Tokyo) 46(3), 441-454 (1993).
2. Schaefer, A.L., Hanzelka, B.L., Eberhard, A., et al. Quorum sensing in Vibrio fischeri: Probing autoinducer-LuxR interactions with autoinducer analogs. J. Bacteriol. 178(10), 2897-2901 (1996).

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)
SCRBQXWVQAXYJP-ZETCQYMHSA-N
InChi (Click to copy)
InChI=1S/C9H13NO4/c1-2-6(11)5-8(12)10-7-3-4-14-9(7)13/h7H,2-5H2,1H3,(H,10,12)/t7-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(=O)CC

Other Databases

PubChem CID
11820073
Cayman ID
13201

Calculated Physicochemical Properties

Heavy Atoms 14
Rings 1
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 190.14
Topological Polar Surface Area 74.54
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 0.36
Molar Refractivity 48.42

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Created at
2nd Jul 2019
Updated at
2nd Jul 2019