Structure Database (LMSD)

OH O O N H O
Common Name
N-(3-hydroxy-octanoyl)-homoserine lactone
Systematic Name
N-(3-hydroxy-octanoyl)-homoserine lactone
Synonyms
  • 3-hydroxy-C8-HSL
  • 3OH-C8-HSL
LM ID
LMFA08030036
Formula
C12H21NO4
Exact Mass
Calculate m/z
243.147059
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Fatty acyl homoserine lactones [FA0803]

String Representations

InChiKey (Click to copy)
XCZVBYOXRSFQBH-AXDSSHIGSA-N
InChi (Click to copy)
InChI=1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)/t9?,10-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(O)CCCCC

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue,
Appl Environ Microbiol, 2007
Pubmed ID: 17085703
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

Other Databases

CHEBI ID
182509
PubChem CID
66769741
Cayman ID
9001150

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 1
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 244.68
Topological Polar Surface Area 77.70
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 1.61
Molar Refractivity 63.79

Admin

Created at
2nd Jul 2019
Updated at
24th Jun 2024