(S)-ARN2508   Click here for help

GtoPdb Ligand ID: 8999

Synonyms: compound (+)-10r [PMID: 26774927] | example 20 [WO2014023643]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: (S)-ARN2508 is a dual inhibitor of fatty acid amide hydrolase (FAAH) and COX enzyme activities [3], claimed in patent WO2014023643 [1]. The compound series developed by Migliore et al. (2015) [3] is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor URB597 and the COX inhibitor flurbiprofen. From this series, the (S) enantiomer was found to inhibit both enzymes, whereas the (R) enantiomer ((R)-ARN2508) only inhibited FAAH.
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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
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 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 75.63
Molecular weight 387.18
XLogP 5.68
No. Lipinski's rules broken 1

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 CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)C(C(=O)O)C
Isomeric SMILES CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)[C@@H](C(=O)O)C
InChI InChI=1S/C22H26FNO4/c1-3-4-5-6-12-24-22(27)28-18-9-7-8-17(13-18)19-11-10-16(14-20(19)23)15(2)21(25)26/h7-11,13-15H,3-6,12H2,1-2H3,(H,24,27)(H,25,26)/t15-/m0/s1
InChI Key USQOVYLRWBOSQC-HNNXBMFYSA-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. DE Vivi M, Scaparelli R, Cavalli A, Migliore M, Piomelli D, Habrant D, Favia. (2014)
Multitarget FAAH and COX inhibitors and therapeutical uses thereof.
Patent number: WO2014023643 A1. Assignee: Fondazione Istituto Italiano Di Tecnologia. Priority date: 06/08/2012. Publication date: 13/02/2014.
2. Grim TW, Ghosh S, Hsu KL, Cravatt BF, Kinsey SG, Lichtman AH. (2014)
Combined inhibition of FAAH and COX produces enhanced anti-allodynic effects in mouse neuropathic and inflammatory pain models.
Pharmacol Biochem Behav, 124: 405-11. [PMID:25058512]
3. Migliore M, Habrant D, Sasso O, Albani C, Bertozzi SM, Armirotti A, Piomelli D, Scarpelli R. (2016)
Potent multitarget FAAH-COX inhibitors: Design and structure-activity relationship studies.
Eur J Med Chem, 109: 216-37. [PMID:26774927]
4. Palermo G, Favia AD, Convertino M, De Vivo M. (2016)
The Molecular Basis for Dual Fatty Acid Amide Hydrolase (FAAH)/Cyclooxygenase (COX) Inhibition.
ChemMedChem, 11 (12): 1252-8. [PMID:26593700]
5. Sasso O, Migliore M, Habrant D, Armirotti A, Albani C, Summa M, Moreno-Sanz G, Scarpelli R, Piomelli D. (2015)
Multitarget fatty acid amide hydrolase/cyclooxygenase blockade suppresses intestinal inflammation and protects against nonsteroidal anti-inflammatory drug-dependent gastrointestinal damage.
FASEB J, 29 (6): 2616-27. [PMID:25757568]