OCT2013   Click here for help

GtoPdb Ligand ID: 11803

Synonyms: lidocaine N-oxide
Compound class: Synthetic organic
Comment: OCT2013 is an aliphatic amine N-oxide that is converted to lidocaine in vivo [1]. This conversion can occur in the reducing environment of the ischaemic myocardium, an effect that may offer an alternative to lidocaine to produce conduction block during ventricular tachyarrhythmias.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 52.16
Molecular weight 250.17
XLogP 1.85
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CC[N+](CC(=O)Nc1c(C)cccc1C)(CC)[O-]
Isomeric SMILES Cc1c(NC(=O)C[N+](CC)(CC)[O-])c(ccc1)C
InChI InChI=1S/C14H22N2O2/c1-5-16(18,6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
InChI Key YDVXPJXUHRROBA-UHFFFAOYSA-N
Bioactivity Comments
OCT2013 prevents ischaemia-induced ventricular fibrillation in isolated rat hearts without causing the adverse effects observed with lidocaine, and provides an antiarrhythmic action in ischaemia-induced arrhythmias in rats in vivo.