compound 66 [PMID: 19788238]   

GtoPdb Ligand ID: 8141

Compound class: Synthetic organic
Comment: Compound 66 is reported as a potent ephrin receptor inhibitor designed as part of a structure-based optimisation study [1]. Compound 66 inhibits all ephrin receptors except EphA7 (1118nM) with low nanomolar IC50s (1-40nM) [1]. Modelling suggests that EphA7 is an outlier as it has a bulky isoleucine residue at its gatekeeper position, compared to a smaller threonine in this position in all of the other ephrin receptors[1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 106.03
Molecular weight 417.14
XLogP 5.2
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COc1ccccc1n1c(cn2c1nc1c2c(=O)[nH]c(=O)n1C)c1cc(O)ccc1C
Isomeric SMILES COc1ccccc1n1c(cn2c1nc1c2c(=O)[nH]c(=O)n1C)c1cc(O)ccc1C
InChI InChI=1S/C22H19N5O4/c1-12-8-9-13(28)10-14(12)16-11-26-18-19(25(2)22(30)24-20(18)29)23-21(26)27(16)15-6-4-5-7-17(15)31-3/h4-11,28H,1-3H3,(H,24,29,30)
InChI Key JTWMOWRMSZZHDR-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione
Database Links
ChEMBL Ligand CHEMBL566515
GtoPdb PubChem SID 249565821
PubChem CID 44478401
RCSB PDB Ligand L66
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SynPHARM 81491 (in complex with EPH receptor A3)