Structure Database (LMSD)
Common Name
N-(3-oxo-hexadecanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-hexadecanoyl)-homoserine lactone
Synonyms
- 3O-C16-HSL
3D model of N-(3-oxo-hexadecanoyl)-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-hexadecanoyl-L-Homoserine lactone is an unusual, substituted, long-chain N-acyl-homoserine lactone (AHL) produced by some bacteria, including strains of Agrobacterium vitis and Pseudomonas.1,2 Like other AHLs, this C16-containing form is thought to be involved in quorum sensing. Substituted, long-chain AHLs, including N-3-oxo-tetradecanoyl-L-homoserine lactone , prime for systemic acquired resistance to pathogen attack in plants.3
This information has been provided by Cayman Chemical
References
3. Schenk, S.T., and Schikora, A. AHL-priming functions via oxylipin and salicylic acid. Front. Plant Sci. 14(5), 784 (2015).
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 sp. W3-1-3
(#1834383)
Gammaproteobacteria
(#1236)
Unusual long-chain N-acyl homoserine lactone production by and presence of quorum quenching activity in bacterial isolates from diseased tilapia fish.,
PLoS One, 2012
PLoS One, 2012
Pubmed ID:
22952864
String Representations
InChiKey (Click to copy)
YZBAMTUXUHIYCQ-SFHVURJKSA-N
InChi (Click to copy)
InChI=1S/C20H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-19(23)21-18-14-15-25-20(18)24/h18H,2-16H2,1H3,(H,21,23)/t18-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
380.44
Topological Polar Surface Area
74.54
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
5
logP
4.65
Molar Refractivity
99.21
Admin
Created at
-
Updated at
20th Nov 2020