ARN726   Click here for help

GtoPdb Ligand ID: 9178

Synonyms: ARN-726 | compound 6 [PMID: 25874594]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: ARN726 is from a series of β-lactam derivatives that are potent, selective, and systemically active inhibitors of intracellular N-Acylethanolamine acid amidase (NAAA) by covalently binding the enzyme's catalytic cysteine. It exhibits anti-inflammatory effects in both mouse models and human macrophages [2]. In the corresponding patent [1] the structure seems to be example 5. There is a patchy SAR table for 106 structures on page 104 of the WO2014144836 PDF. The R isomer of this structure PubChem CID 86282216 is reported to be less active.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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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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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.43
Molecular weight 268.18
XLogP 3.74
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=C(NC1CNC1=O)OCCCCC1CCCCC1
Isomeric SMILES O=C(N[C@H]1CNC1=O)OCCCCC1CCCCC1
InChI InChI=1S/C14H24N2O3/c17-13-12(10-15-13)16-14(18)19-9-5-4-8-11-6-2-1-3-7-11/h11-12H,1-10H2,(H,15,17)(H,16,18)/t12-/m0/s1
InChI Key FNLUJRBWJBUJTC-LBPRGKRZSA-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/)
References
1. Piomelli D. et al.. (2014)
Carbamate derivatives of lactam based n-acylethanolamine acid amidase (NAAA) inhibitors.
Patent number: WO2014144836. Assignee: Regents Of The University Of California. Priority date: 15/03/2013. Publication date: 18/09/2014.
2. Ribeiro A, Pontis S, Mengatto L, Armirotti A, Chiurchiù V, Capurro V, Fiasella A, Nuzzi A, Romeo E, Moreno-Sanz G et al.. (2015)
A Potent Systemically Active N-Acylethanolamine Acid Amidase Inhibitor that Suppresses Inflammation and Human Macrophage Activation.
ACS Chem Biol, 10 (8): 1838-46. [PMID:25874594]