Structure Database (LMSD)
Common Name
N-(3-hydroxy-butanoyl)-homoserine lactone
Systematic Name
N-(3-hydroxy-butanoyl)-homoserine lactone
Synonyms
- 3-hydroxy-C4:0-HSL
3D model of N-(3-hydroxy-butanoyl)-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-hydroxybutyryl-L-Homoserine lactone is an N-acyl-homoserine lactone produced by the bacterium V. splendidus and has been found in sequencing batch biofilm reactors used in wastewater treatment.1,2 It is the racemic version of the V. harveyi autoinducer N-((R)-3-hydroxybutanoyl)-L-homoserine lactone.3
This information has been provided by Cayman Chemical
References
3. Ke, X., Miller, L.C., and Bassler, B.L. Determinants governing ligand specificity of the Vibrio harveyi LuxN quorum-sensing receptor. Mol. Microbiol. 95(1), 127-142 (2015).
References
Reference
Detection of acyl-homoserine lactones by Escherichia and Salmonella. Jitesh A. Soares and Brian M. M. Ahmer. Current Opinion in Microbiology. Volume 14, Issue 2, April 2011, Pages 188-193. https://doi.org/10.1016/j.mib.2011.01.006
https://www.sciencedirect.com/science/article/pii/S136952741100018X#bib0080
https://www.sciencedirect.com/science/article/pii/S136952741100018X#bib0080
String Representations
InChiKey (Click to copy)
FIXDIFPJOFIIEC-GDVGLLTNSA-N
InChi (Click to copy)
InChI=1S/C8H13NO4/c1-5(10)4-7(11)9-6-2-3-13-8(6)12/h5-6,10H,2-4H2,1H3,(H,9,11)/t5?,6-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(O)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
13
Rings
1
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
175.48
Topological Polar Surface Area
77.70
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
0.05
Molar Refractivity
45.32
Admin
Created at
1st Jul 2019
Updated at
2nd Jul 2019