Structure Database (LMSD)
Common Name
N-(3-oxododecanoyl) homoserine lactone
Systematic Name
N-(3-oxododecanoyl) homoserine lactone
Synonyms
3D model of N-(3-oxododecanoyl) homoserine lactone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
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
Admin
Created at
-
Updated at
17th Nov 2020