MS39   Click here for help

GtoPdb Ligand ID: 10634

Synonyms: compound 6 [PMID: 31895569]
Compound class: Synthetic organic
Comment: MS39 is a PROTAC (proteolysis targeting chimera). It is a hybrid molecule that simultaneously inhibits EGFR kinase activity and targets EGFR for destruction via ubiquitination and proteasomal degradation [2]. The kinase inhibitor portion of the molecule is derived from the first generation EGFR inhibitor gefitinib and it uses a VHL ligand to engage the E3 ligase system.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 4
Rotatable bonds 29
Topological polar surface area 219.69
Molecular weight 1055.49
XLogP 7.78
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc2ncnc(c2cc1OCCCN1CCN(CC1)C(=O)CCCCCCCCCC(=O)NC(C(C)(C)C)C(=O)N1CC(CC1C(=O)NCc1ccc(cc1)c1scnc1C)O)Nc1ccc(c(c1)Cl)F
Isomeric SMILES COc1cc2ncnc(c2cc1OCCCN1CCN(CC1)C(=O)CCCCCCCCCC(=O)N[C@@H](C(C)(C)C)C(=O)N1C[C@@H](C[C@H]1C(=O)NCc1ccc(cc1)c1scnc1C)O)Nc1ccc(c(c1)Cl)F
InChI InChI=1S/C55H71ClFN9O7S/c1-36-50(74-35-61-36)38-18-16-37(17-19-38)32-58-53(70)45-29-40(67)33-66(45)54(71)51(55(2,3)4)63-48(68)14-11-9-7-6-8-10-12-15-49(69)65-25-23-64(24-26-65)22-13-27-73-47-30-41-44(31-46(47)72-5)59-34-60-52(41)62-39-20-21-43(57)42(56)28-39/h16-21,28,30-31,34-35,40,45,51,67H,6-15,22-27,29,32-33H2,1-5H3,(H,58,70)(H,63,68)(H,59,60,62)/t40-,45+,51-/m1/s1
InChI Key HLFLODKZIGYHNR-LTEFSYCBSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
(2S,4R)-1-((S)-2-(11-(4-(3-((4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)piperazin-1-yl)-11-oxoundecanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Synonyms Click here for help
compound 6 [PMID: 31895569]
Database Links Click here for help
GtoPdb PubChem SID 404859081
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