BSJ-03-123   Click here for help

GtoPdb Ligand ID: 10532

Compound class: Synthetic organic
Comment: BSJ-03-123 is a PROTAC (proteolysis targeting chimera) [1]. It is a hybrid molecule that simultaneously inhibits CDK4/CDK6 kinase activity and recruits E3 ligase CRL4CRBN to target the kinases for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. BSJ-03-123 is a palbociclib-based selective CDK6 degrader.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 3
Rotatable bonds 22
Topological polar surface area 245.82
Molecular weight 936.41
XLogP 2.09
No. Lipinski's rules broken 2
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Canonical SMILES O=C(COc1cccc2c1C(=O)N(C2=O)C1CCC(=O)NC1=O)NCCOCCOCCOCCN1CCN(CC1)c1ccc(nc1)Nc1ncc2c(n1)n(C1CCCC1)c(=O)c(c2C)C(=O)C
Isomeric SMILES O=C(COc1cccc2c1C(=O)N(C2=O)C1CCC(=O)NC1=O)NCCOCCOCCOCCN1CCN(CC1)c1ccc(nc1)Nc1ncc2c(n1)n(C1CCCC1)c(=O)c(c2C)C(=O)C
InChI InChI=1S/C47H56N10O11/c1-29-34-27-50-47(53-42(34)56(31-6-3-4-7-31)45(63)40(29)30(2)58)51-37-12-10-32(26-49-37)55-17-15-54(16-18-55)19-21-66-23-25-67-24-22-65-20-14-48-39(60)28-68-36-9-5-8-33-41(36)46(64)57(44(33)62)35-11-13-38(59)52-43(35)61/h5,8-10,12,26-27,31,35H,3-4,6-7,11,13-25,28H2,1-2H3,(H,48,60)(H,52,59,61)(H,49,50,51,53)
1. Jiang B, Wang ES, Donovan KA, Liang Y, Fischer ES, Zhang T, Gray NS. (2019)
Development of Dual and Selective Degraders of Cyclin-Dependent Kinases 4 and 6.
Angew Chem Int Ed Engl, 58 (19): 6321-6326. [PMID:30802347]