compound 20 [PMID: 30998356]   Click here for help

GtoPdb Ligand ID: 10371

PDB Ligand
Compound class: Synthetic organic
Comment: Compound 20 was rationally designed as a potent, selective and orally active TTK protein kinase inhibitor with single agent efficacy against triple negative breast cancer cells [1]. The pyrrolopyrimidine core of 20 interacts with residues within TTK's ATP binding pocket, and it forms three hydrogen bonds to the hinge region. The ligand/TTK co-crystal structure has been submitted to the PDB and has ID 6N6O.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 112.6
Molecular weight 555.19
XLogP 6.12
No. Lipinski's rules broken 1
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Canonical SMILES CN(C(=O)c1ccc(c(c1)OC(C(F)(F)F)C)Nc1nc(OC2CCC(CC2)(C)O)c2c(n1)[nH]cc2Cl)C
Isomeric SMILES CN(C(=O)c1ccc(c(c1)O[C@@H](C(F)(F)F)C)Nc1nc(O[C@@H]2CC[C@](CC2)(C)O)c2c(n1)[nH]cc2Cl)C
InChI InChI=1S/C25H29ClF3N5O4/c1-13(25(27,28)29)37-18-11-14(22(35)34(3)4)5-6-17(18)31-23-32-20-19(16(26)12-30-20)21(33-23)38-15-7-9-24(2,36)10-8-15/h5-6,11-13,15,36H,7-10H2,1-4H3,(H2,30,31,32,33)/t13-,15-,24+/m1/s1
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Molecular structure representations generated using Open Babel