compound 3 [PMID: 31804822]   Click here for help

GtoPdb Ligand ID: 10606

Compound class: Synthetic organic
Comment: Compound 3 is a PROTAC (proteolysis targeting chimera). It is a hybrid molecule that simultaneously inhibits MEK kinase activity and recruits E3 ligase via a Von Hippel-Lindau ligand to promote proteasomal degradation of MEK protein [1]. The kinase inhibitor component of the molecule is an analogue of the allosteric MEK inhibitor refametinib.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 17
Hydrogen bond donors 6
Rotatable bonds 30
Topological polar surface area 285.24
Molecular weight 1200.33
XLogP 6.17
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES O=C(CCc1ccc(cc1)S(=O)(=O)Nc1cc(C)c(=O)n(c1Nc1ccc(cc1F)I)C)NCCOCCOCCOCC(=O)NC(C(C)(C)C)C(=O)N1CC(CC1C(=O)NC(c1ccc(cc1)c1scnc1C)C)O
Isomeric SMILES O=C(CCc1ccc(cc1)S(=O)(=O)Nc1cc(C)c(=O)n(c1Nc1ccc(cc1F)I)C)NCCOCCOCCOCC(=O)N[C@@H](C(C)(C)C)C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@H](c1ccc(cc1)c1scnc1C)C)O
InChI InChI=1S/C53H66FIN8O11S2/c1-32-26-43(49(62(7)51(32)68)59-42-18-15-38(55)27-41(42)54)61-76(70,71)40-16-8-35(9-17-40)10-19-45(65)56-20-21-72-22-23-73-24-25-74-30-46(66)60-48(53(4,5)6)52(69)63-29-39(64)28-44(63)50(67)58-33(2)36-11-13-37(14-12-36)47-34(3)57-31-75-47/h8-9,11-18,26-27,31,33,39,44,48,59,61,64H,10,19-25,28-30H2,1-7H3,(H,56,65)(H,58,67)(H,60,66)/t33-,39+,44-,48+/m0/s1
InChI Key RQBUNBWHIATPNI-WQWWALRQSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
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GtoPdb PubChem SID 404859053
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