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CCX354   Click here for help

GtoPdb Ligand ID: 10164

Synonyms: CCX 354 | CCX-354 | CCX-354-C
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: CCX354 is an orally active CCR1 antagonist that was originally developed by Chemocentryx for anti-inflammatory/immunomodulatory potential. The chemical structure is claimed as Example 16 in patent WO2008147815A1 [1]. The structure in the patent resolves to PubChem CID 25016615, which is a tautomeric representation of the claimed structure.

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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 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 91.11
Molecular weight 451.15
XLogP 2.67
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 COc1cc(ccc1Cl)N1CCN(CC1)C(=O)Cn1[nH]c(=C2N=CC=N2)c2c1nccc2
Isomeric SMILES COc1cc(ccc1Cl)N1CCN(CC1)C(=O)Cn1[nH]c(=C2N=CC=N2)c2c1nccc2
InChI InChI=1S/C22H22ClN7O2/c1-32-18-13-15(4-5-17(18)23)28-9-11-29(12-10-28)19(31)14-30-22-16(3-2-6-26-22)20(27-30)21-24-7-8-25-21/h2-8,13,27H,9-12,14H2,1H3
InChI Key WSVDLXWYJRCDBZ-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/)
References
1. Li L, Pennell AMK, Zhang P. (2008)
3-(imidazolyl)-pyrazolo[3,4-b]pyridines.
Patent number: WO2008147815A1. Assignee: Chemocentryx, Inc.. Priority date: 22/05/2007. Publication date: 04/12/2008.
2. Tak PP, Balanescu A, Tseluyko V, Bojin S, Drescher E, Dairaghi D, Miao S, Marchesin V, Jaen J, Schall TJ et al.. (2013)
Chemokine receptor CCR1 antagonist CCX354-C treatment for rheumatoid arthritis: CARAT-2, a randomised, placebo controlled clinical trial.
Ann Rheum Dis, 72 (3): 337-44. [PMID:22589376]