MS8815   Click here for help

GtoPdb Ligand ID: 12138

Synonyms: compound 16 [PMID: 35837138] | MS-8815
Compound class: Synthetic organic
Comment: MS8815 is a bifunctional PROTAC molecule that targets the enhancer of zeste homolog 2 (EZH2) protein for degradation [1]. It contains a VHL-binding ligand VHL-1 (a.k.a. VH032 [3]; PubChem CID 77232228; Kd 188 nM) to recruit the VHL E3 ligase, and the EZH2 engager is the FDA-approved drug tazemetostat (EPZ-6438). EZH2 overexpression is a marker of poor prognosis in triple-negative breast cancer (TNBC). Protein degrading agents are proposed as alternatives to small molecule inhibitors, and are of particular use for 'difficult-to-drug' protein targets.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 5
Rotatable bonds 29
Topological polar surface area 237.85
Molecular weight 1153.64
XLogP 9.07
No. Lipinski's rules broken 3
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Canonical SMILES CCN(c1cc(cc(c1C)C(=O)NCc1c(C)cc([nH]c1=O)C)c1ccc(cc1)CN1CCN(CC1)C(=O)CCCCCCCC(=O)N[C@@H](C(C)(C)C)C(=O)N1C[C@@H](C[C@H]1C(=O)NCc1ccc(cc1)c1scnc1C)O)C1CCOCC1
Isomeric SMILES Cc1c(c(=O)[nH]c(c1)C)CNC(=O)c1cc(cc(c1C)N(C1CCOCC1)CC)c1ccc(cc1)CN1CCN(CC1)C(=O)CCCCCCCC(=O)N[C@H](C(=O)N1[C@@H](C[C@H](C1)O)C(=O)NCc1ccc(cc1)c1c(ncs1)C)C(C)(C)C
InChI InChI=1S/C65H87N9O8S/c1-9-73(51-25-31-82-32-26-51)55-35-50(34-53(44(55)4)61(78)67-38-54-42(2)33-43(3)69-62(54)79)48-21-19-47(20-22-48)39-71-27-29-72(30-28-71)58(77)16-14-12-10-11-13-15-57(76)70-60(65(6,7)8)64(81)74-40-52(75)36-56(74)63(80)66-37-46-17-23-49(24-18-46)59-45(5)68-41-83-59/h17-24,33-35,41,51-52,56,60,75H,9-16,25-32,36-40H2,1-8H3,(H,66,80)(H,67,78)(H,69,79)(H,70,76)/t52-,56+,60-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
Synonyms Click here for help
compound 16 [PMID: 35837138] | MS-8815
Database Links Click here for help
GtoPdb PubChem SID 472319260
PubChem CID 165368931
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