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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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.

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

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
Search Google for chemical match using the InChIKey IOJUJUOXKXMJNF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IOJUJUOXKXMJNF
UniChem Compound Search for chemical match using the InChIKey IOJUJUOXKXMJNF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IOJUJUOXKXMJNF-UHFFFAOYSA-N
Wikipedia Nitroaspirin