AZD6703   Click here for help

GtoPdb Ligand ID: 7687

Synonyms: AZ 12012199 | AZ-12012199 | AZ12012199 | AZD 6703 | AZD-6703
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZD6703 is a potent, selective and reversible orally bioavailable inhibitor of p38 mitogen-activated protein kinase 14 (MAPK14).
This compound was in the AstraZeneca/MRC repurposing list from 2011.
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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 CDK toolkit. 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 69.95
Molecular weight 417.22
XLogP 3.31
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN1CCN(CC1)c1ccc2c(c1)c(=O)n(cn2)c1cc(ccc1C)C(=O)NC1CC1
Isomeric SMILES CN1CCN(CC1)c1ccc2c(c1)c(=O)n(cn2)c1cc(ccc1C)C(=O)NC1CC1
InChI InChI=1S/C24H27N5O2/c1-16-3-4-17(23(30)26-18-5-6-18)13-22(16)29-15-25-21-8-7-19(14-20(21)24(29)31)28-11-9-27(2)10-12-28/h3-4,7-8,13-15,18H,5-6,9-12H2,1-2H3,(H,26,30)
InChI Key ZMAZXHICVRYLQN-UHFFFAOYSA-N
References
1. Brown DS, Cumming JG, Bethel P, Finlayson J, Gerhardt S, Nash I, Pauptit RA, Pike KG, Reid A, Snelson W et al.. (2012)
The discovery of N-cyclopropyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzamide (AZD6703), a clinical p38α MAP kinase inhibitor for the treatment of inflammatory diseases.
Bioorg Med Chem Lett, 22 (12): 3879-83. [PMID:22608965]
2. Clark JE, Sarafraz N, Marber MS. (2007)
Potential of p38-MAPK inhibitors in the treatment of ischaemic heart disease.
Pharmacol Ther, 116 (2): 192-206. [PMID:17765316]
3. Saklatvala J. (2004)
The p38 MAP kinase pathway as a therapeutic target in inflammatory disease.
Curr Opin Pharmacol, 4 (4): 372-7. [PMID:15251131]
4. Schieven GL. (2005)
The biology of p38 kinase: a central role in inflammation.
Curr Top Med Chem, 5 (10): 921-8. [PMID:16178737]