Structure Database (LMSD)
Common Name
N-(3-oxo-butanoyl)-homoserine lactone
Systematic Name
N-(3-oxo-butanoyl)-homoserine lactone
Synonyms
- 3-oxo-C4:0-HSL
3D model of N-(3-oxo-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-oxo-butyryl-L-Homoserine lactone is a bacterial quorum-sensing signaling molecule.1 It induces expression of rhiI in R. leguminosarum, a gene with roles in the interaction of the rhizosphere with legumes.
This information has been provided by Cayman Chemical
References
1. Rodelas, B., Lithgow, J.K., Wisniewski-Dye, F., et al. Analysis of quorum-sensing-dependent control of rhizosphere-expressed (rhi) genes in Rhizobium leguminosarum bv. viciae. J. Bacteriol. 181(12), 3816-3823 (1999).
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)
FIHPLICEAUNEFV-LURJTMIESA-N
InChi (Click to copy)
InChI=1S/C8H11NO4/c1-5(10)4-7(11)9-6-2-3-13-8(6)12/h6H,2-4H2,1H3,(H,9,11)/t6-/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
172.84
Topological Polar Surface Area
74.54
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
5
logP
-0.03
Molar Refractivity
43.81
Admin
Created at
1st Jul 2019
Updated at
1st Jul 2019