GW766994   Click here for help

GtoPdb Ligand ID: 9680

Synonyms: GSK766994 | GW-766994
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: GW766994 is an investigational CCR3 antagonist [5].
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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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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 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 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 96.69
Molecular weight 450.12
XLogP 2.39
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 O=C(NCc1ccc(cc1)C(=O)N)NCC1OCCN(C1)Cc1ccc(c(c1)Cl)Cl
Isomeric SMILES O=C(NCc1ccc(cc1)C(=O)N)NC[C@H]1OCCN(C1)Cc1ccc(c(c1)Cl)Cl
InChI InChI=1S/C21H24Cl2N4O3/c22-18-6-3-15(9-19(18)23)12-27-7-8-30-17(13-27)11-26-21(29)25-10-14-1-4-16(5-2-14)20(24)28/h1-6,9,17H,7-8,10-13H2,(H2,24,28)(H2,25,26,29)/t17-/m1/s1
InChI Key GPLUUMAKBFSDIE-QGZVFWFLSA-N
References
1. Conroy DM, Humbles AA, Rankin SM, Palframan RT, Collins PD, Griffiths-Johnson DA, Jose PJ, Williams TJ. (1997)
The role of the eosinophil-selective chemokine, eotaxin, in allergic and non-allergic airways inflammation.
Mem Inst Oswaldo Cruz, 92 Suppl 2: 183-91. [PMID:9698931]
2. Kitaura M, Nakajima T, Imai T, Harada S, Combadiere C, Tiffany HL, Murphy PM, Yoshie O. (1996)
Molecular cloning of human eotaxin, an eosinophil-selective CC chemokine, and identification of a specific eosinophil eotaxin receptor, CC chemokine receptor 3.
J Biol Chem, 271 (13): 7725-30. [PMID:8631813]
3. Méndez-Enríquez E, Medina-Tamayo J, Soldevila G, Fortoul TI, Anton B, Flores-Romo L, García-Zepeda EA. (2014)
A CCL chemokine-derived peptide (CDIP-2) exerts anti-inflammatory activity via CCR1, CCR2 and CCR3 chemokine receptors: Implications as a potential therapeutic treatment of asthma.
Int Immunopharmacol, 20 (1): 1-11. [PMID:24560857]
4. Neighbour H, Boulet LP, Lemiere C, Sehmi R, Leigh R, Sousa AR, Martin J, Dallow N, Gilbert J, Allen A et al.. (2014)
Safety and efficacy of an oral CCR3 antagonist in patients with asthma and eosinophilic bronchitis: a randomized, placebo-controlled clinical trial.
Clin Exp Allergy, 44 (4): 508-16. [PMID:24286456]
5. Pease J, Horuk R. (2012)
Chemokine receptor antagonists.
J Med Chem, 55 (22): 9363-92. [PMID:22931505]
6. Pease JE, Horuk R. (2014)
Recent progress in the development of antagonists to the chemokine receptors CCR3 and CCR4.
Expert Opin Drug Discov, 9 (5): 467-83. [PMID:24641500]
7. Thomson NC. (2014)
Novel therapies targeting eosinophilic inflammation in asthma.
Clin Exp Allergy, 44 (4): 462-8. [PMID:24666518]