ER-27319   Click here for help

GtoPdb Ligand ID: 9611

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The structure shown here is ER-27319 free base, when in fact the biological activity has been evaluated using the ethanedioate as represented by PubChem CID 9799508 [1]. ER-27319 is an inhibitor of spleen tyrosine kinase (Syk) [2] however, given the high concentration of compound ER-27319 required to cause half-maximal inhibition of mast cells degranulation, targets other than Syk may also be inhibited. In addition ER-27319 targets the activation of SYK mediated through FcεR1γ ITAM, suggesting there is no direct interaction with the Syk ATP pocket. Whatever the mechanism ER-27319 action is specific to mast cells.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 48.02
Molecular weight 280.16
XLogP 5.12
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES NCCCn1c2ccccc2c(=O)c2c1c(C)c(C)cc2
Isomeric SMILES NCCCn1c2ccccc2c(=O)c2c1c(C)c(C)cc2
InChI InChI=1S/C18H20N2O/c1-12-8-9-15-17(13(12)2)20(11-5-10-19)16-7-4-3-6-14(16)18(15)21/h3-4,6-9H,5,10-11,19H2,1-2H3
InChI Key CFPDEQBPNROZDC-UHFFFAOYSA-N
References
1. Moriya K, Rivera J, Odom S, Sakuma Y, Muramato K, Yoshiuchi T, Miyamoto M, Yamada K. (1997)
ER-27319, an acridone-related compound, inhibits release of antigen-induced allergic mediators from mast cells by selective inhibition of fcepsilon receptor I-mediated activation of Syk.
Proc Natl Acad Sci USA, 94 (23): 12539-44. [PMID:9356485]
2. Singh R, Masuda ES, Payan DG. (2012)
Discovery and development of spleen tyrosine kinase (SYK) inhibitors.
J Med Chem, 55 (8): 3614-43. [PMID:22257213]