Structure Database (LMSD)

Common Name
N-(3-oxo-decanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-decanoyl)-homoserine lactone
Synonyms
  • 3O-C10-HSL
LM ID
LMFA08030017
Formula
C14H23NO4
Exact Mass
Calculate m/z
269.162709
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

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-decanoyl-L-Homoserine lactone is a quorum-sensing signaling molecule that is produced by bacteria in response to increasing cell density.1 It increases expression of the bacterial conjugation gene tra in A. tumefaciens in a reporter cell assay. N-3-oxo-decanoyl-L-Homoserine lactone (100 nM) induces adventitious root formation and increases expression of the auxin-response genes AUX22c and AUX22d and the cell division genes CDC2, ARC, and CDPK in mung bean seedlings.2 It decreases expression of glucanase genes in A. thaliana when used at a concentration of 6 µM.3

This information has been provided by Cayman Chemical

References

1. Zhang, L., Murphy, P.J., Kerr, A., et al. Agrobacterium conjugation and gene regulation by N-acyl-L-homoserine lactones. Nature 362(6419), 446-448 (1993).
2. Bai, X., Todd, C.D., Desikan, R., et al. N-3-oxo-decanoyl-L-homoserine-lactone activates auxin-induced adventitious root formation via hydrogen peroxide- and nitric oxide-dependent cyclic GMP signaling in mung bean. Plant Physiol. 158(2), 725-736 (2012).
3. Schenk, S.T., Hernández-Reyes, C., Samans, B., et al. N-acyl-homoserine lactone primes plants for cell wall reinforcement and induces resistance to bacterial pathogens via the salicylic acid/oxylipin pathway. Plant Cell 26(6), 2708-2723 (2014).

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
Sinorhizobium meliloti (#382)
Alphaproteobacteria (#28211)
Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-acyl homoserine lactones.,
J Bacteriol, 2002
Pubmed ID: 12270827

String Representations

InChiKey (Click to copy)
KYGIKEQVUKTKRR-LBPRGKRZSA-N
InChi (Click to copy)
InChI=1S/C14H23NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h12H,2-10H2,1H3,(H,15,17)/t12-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(=O)CCCCCCC

Other Databases

CHEBI ID
184905
PubChem CID
10221060
Cayman ID
13026
PDB ID
3M5

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 276.64
Topological Polar Surface Area 74.54
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 5
logP 2.31
Molar Refractivity 71.51

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