MK-8353   Click here for help

GtoPdb Ligand ID: 9974

Synonyms: MK8353 | SCH900353
PDB Ligand
Compound class: Synthetic organic
Comment: MK-8353 (formerly know as SCH900353) is an orally bioavailable dual mechanism ERK1/2 inhibitor, i.e. it inhibits ERK1/2 catalytic activity and phosphorylation of ERK1/2 [1]. It has improved pharmacokinetic properties in comparison to SCH772984 (a preclinical ERK1/2 inhibtor tool compound) and has shown preliminary anti-tumour efficacy in patients with BRAF or RAS mutated metastatic melanoma and colorectal cancers.
(Note: ERK1= MAPK3, ERK2= MAPK1).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 159.46
Molecular weight 691.31
XLogP 5.1
No. Lipinski's rules broken 1
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Canonical SMILES CSC1(CCN(C1)CC(=O)N1CCC(=CC1)c1ccc(cc1)c1ncn(n1)C)C(=O)Nc1ccc2c(c1)c(n[nH]2)c1ccc(nc1)OC(C)C
Isomeric SMILES CS[C@]1(CCN(C1)CC(=O)N1CCC(=CC1)c1ccc(cc1)c1ncn(n1)C)C(=O)Nc1ccc2c(c1)c(n[nH]2)c1ccc(nc1)OC(C)C
InChI InChI=1S/C37H41N9O3S/c1-24(2)49-32-12-9-28(20-38-32)34-30-19-29(10-11-31(30)41-42-34)40-36(48)37(50-4)15-18-45(22-37)21-33(47)46-16-13-26(14-17-46)25-5-7-27(8-6-25)35-39-23-44(3)43-35/h5-13,19-20,23-24H,14-18,21-22H2,1-4H3,(H,40,48)(H,41,42)/t37-/m0/s1
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Molecular structure representations generated using Open Babel