Structure Database (LMSD)
Common Name
N-(3-hydroxy-decanoyl)-homoserine lactone
Systematic Name
N-(3-hydroxy-decanoyl)-homoserine lactone
Synonyms
- 3-hydroxy-C10-HSL
- 3OH-C10-HSL
3D model of N-(3-hydroxy-decanoyl)-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-hydroxydecanoyl-L-Homoserine lactone is a bacterial quorum-sensing molecule that has been found in B. pseudomallei.1 It induces expression of tda, a gene with roles in the production of the antibiotic tropodithietic acid (TDA) and the algicide roseobacticide, in P. inhibens.2
This information has been provided by Cayman Chemical
References
1. Lumjiaktase, P., Diggle, S.P., Loprasert, S., et al. Quorum sensing regulates dpsA and the oxidative stress response in Burkholderia pseudomallei. Microbiology (Reading) 152(Pt 12), 3651-3659 (2006).
2. Wang, R., Gallant, É., and Seyedsayamdost, M.R. Investigation of the genetics and biochemistry of roseobacticide production in the Roseobacter clade bacterium Phaeobacter inhibens. mBio 7(2), e02118 (2016).
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
Appl Environ Microbiol, 2007
Pubmed ID:
17085703
DOI:
10.1128/AEM.01451-06
String Representations
InChiKey (Click to copy)
DOICJCCMIBBSOO-KIYNQFGBSA-N
InChi (Click to copy)
InChI=1S/C14H25NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h11-12,16H,2-10H2,1H3,(H,15,17)/t11?,12-/m0/s1
SMILES (Click to copy)
[C@@H]1(CCOC1=O)NC(=O)CC(O)CCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
1
Aromatic Rings
0
Rotatable Bonds
9
Van der Waals Molecular Volume
279.28
Topological Polar Surface Area
77.70
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
5
logP
2.39
Molar Refractivity
73.02
Admin
Created at
2nd Jul 2019
Updated at
2nd Jul 2019