NCX-4016   Click here for help

GtoPdb Ligand ID: 9018

Synonyms: NCX 4016 | NCX4016 | nitric oxide-releasing aspirin | nitroaspirin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: NCX-4016 is an inhibitor which supports generation of reactive oxygen species (ROS) that modify CCL2 levels, disabling T cell chemotaxis. It is expected that this type of action will have anti-inflammatory, antiproliferative, and cytoprotective activity [1]. NCX-4016 is a NO-NSAID type compound (nitric oxide-donating NSAID), a hybrid nitrate conjugated to an NSAID, in this case aspirin. This type of compound was designed to exploit the gastroprotective properties of NO bioactivity, to combat the gastrotoxicity which compromises NSAID use [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 104.97
Molecular weight 331.07
XLogP 3.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
Isomeric SMILES [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
InChI InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
InChI Key IOJUJUOXKXMJNF-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Non-steroidal anti-inflammatory ligands
IUPAC Name Click here for help
[3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
Synonyms Click here for help
NCX 4016 | NCX4016 | nitric oxide-releasing aspirin | nitroaspirin
Database Links Click here for help
CAS Registry No. 175033-36-0 (source: PubChem)
ChEMBL Ligand CHEMBL374385
GtoPdb PubChem SID 315661103
PubChem CID 119032
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Wikipedia Nitroaspirin