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
C20H35NO4
Exact Mass
Calculate m/z
353.256609
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Fatty acyl homoserine lactones [FA0803]
Fatty Acids and Conjugates [FA01]
Oxo fatty acids [FA0106]

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

1. Chang, C.-Y., Koh, C.-L., Sam, C.-K., et al. Unusual long-chain N-acyl homoserine lactone production by and presence of quorum quenching activity in bacterial isolates from diseased tilapia fish. PLoS One 7(8), e44034 (2012).
2. Savka, M.A., Le, P.T., and Burr, T.J. LasR receptor for detection of long-chain quorum-sensing signals: identification of N-acyl-homoserine lactones encoded by the avsI locus of Agrobacterium vitis. Curr. Microbiol. 62(1), 101-110 (2011).
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
87606261
Cayman ID
13062

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