Structure Database (LMSD)

Common Name
N-(3-oxododecanoyl) homoserine lactone
Systematic Name
N-(3-oxododecanoyl) homoserine lactone
Synonyms
LM ID
LMFA08030001
Formula
Exact Mass
Calculate m/z
297.194009
Status
Curated



Classification

Biological Context

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex.1,2 It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 µM.3 Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.2

This information has been provided by Cayman Chemical

References

2. Smith, R.S., Fedyk, E.R., Springer, T.A., et al. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-κB and activator protein-2. J. Immunol. 167(1), 366-374 (2001).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Paraburkholderia tropica (#92647)
Betaproteobacteria (#28216)
Structural characterization of N-acyl-homoserine lactones from bacterial quorum sensing using LC-MS/MS analyses after Paternò-Büchi derivatization in solution.,
Anal Bioanal Chem, 2024
Pubmed ID: 38842688
Pseudomonas aeruginosa (#287)
Gammaproteobacteria (#1236)
Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes,
Proc Natl Acad Sci U S A., 1994
Pubmed ID: 8278364

String Representations

InChiKey (Click to copy)
PHSRRHGYXQCRPU-AWEZNQCLSA-N
InChi (Click to copy)
InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
SMILES (Click to copy)
N([C@H]1CCOC1=O)C(CC(=O)CCCCCCCCC)=O

Other Databases

CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings
Rotatable Bonds 11
Van der Waals Molecular Volume 311.24
Topological Polar Surface Area 74.54
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 3.09
Molar Refractivity 80.74

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Created at
-
Updated at
17th Nov 2020