example 5 [WO2023245150]

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Ligands
example 5 [WO2023245150]

GtoPdb Ligand ID: 14089

Compound class: Synthetic organic

Comment: This is one of the more potent compounds claimed in patent WO2023245150A1 (Prelude Therapeutics) as lysine acetyltransferase 6A (KAT6A) degraders [1]. It is a PROTAC heterobifunctional molecule with a thalidomide-based cereblon ubiquitin ligase binding moiety linked to a selective KAT6A binding ligand. It promotes formation of a ternary complex that directs KAT6A protein for proteosomal degradation. This mechanism is proposed as an alternative to direct enzyme inhibition.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	15
Hydrogen bond donors	2
Rotatable bonds	11
Topological polar surface area	194.24
Molecular weight	847.94
XLogP	2.1
No. Lipinski's rules broken	3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey

Canonical SMILES	COC1=CC(=CC2=C1C(=NO2)NS(=O)(=O)C3=CC(=CC=C3)N4CC5(CCN(CC5)CC6CCN(C6)C7=CC=C8C(=C7)C(=O)N(C9CCC(=O)NC9=O)C8=O)C4)CN%10C=CC=N%10
Isomeric SMILES	COC1=CC(CN2C=CC=N2)=CC3=C1C(NS(=O)(=O)C4=CC=CC(=C4)N5CC6(C5)CCN(CC7CCN(C7)C8=CC9=C(C=C8)C(=O)N(C%10CCC(=O)NC%10=O)C9=O)CC6)=NO3
InChI	InChI=1S/C43H45N9O8S/c1-59-35-18-28(24-51-14-3-13-44-51)19-36-38(35)39(46-60-36)47-61(57,58)31-5-2-4-29(20-31)50-25-43(26-50)11-16-48(17-12-43)22-27-10-15-49(23-27)30-6-7-32-33(21-30)42(56)52(41(32)55)34-8-9-37(53)45-40(34)54/h2-7,13-14,18-21,27,34H,8-12,15-17,22-26H2,1H3,(H,46,47)(H,45,53,54)
InChI Key	XVJJGQFASNNHCT-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)