Structure Database (LMSD)

Common Name
N-(3-oxo-hexadecanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-hexadecanoyl)-homoserine lactone
Synonyms
  • 3O-C16-HSL
LM ID
LMFA08030016
Formula
Exact Mass
Calculate m/z
353.256609
Status
Curated

Classification

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
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
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

PubChem CID
Cayman ID

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

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Created at
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Updated at
20th Nov 2020