Structure Database (LMSD)
Common Name
N-(3-oxo-tetradecanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-tetradecanoyl)-homoserine lactone
Synonyms
- 3O-C14-HSL
3D model of N-(3-oxo-tetradecanoyl)-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
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
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
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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