BWA-522

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Ligands
BWA-522

GtoPdb Ligand ID: 12912

Synonyms: BWA522 | compound 28 [PMID: 37556600]

Compound class: Synthetic organic

Comment: BWA-522 is an orally active cereblon-targeting PROTAC degrader of the androgen receptor (AR) [2]. It was designed for potential to treat advanced prostate cancer. BWA-522 binds to the N-terminal domain (NTD) of the AR using a warhead derived from the antagonist EPI-002 (ralaniten) [1]. Exploiting the NTD is proposed as a strategy to target both wild type ARs and mutated ARs that have no ligand-binding domain (LBD) and that are therefore unsusceptible to androgen-competitive antagonist drugs.

BWA-522 is commercially available from our sponsors

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	11
Hydrogen bond donors	2
Rotatable bonds	13
Topological polar surface area	128.72
Molecular weight	771.34
XLogP	4.49
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	CC(C)(C1=CC=C(C=C1)OCC2CCN(CC2)CC3CCN(CC3)C4=CC=C5C(=C4)C(=O)N(C6CCC(=O)NC6=O)C5=O)C7=CC=C(C=C7)OC[C@@H](CCl)O
Isomeric SMILES	ClC[C@H](COC1=CC=C(C=C1)C(C)(C)C2=CC=C(OCC3CCN(CC3)CC4CCN(CC4)C=5C=C6C(N(C(C6=CC5)=O)C7C(NC(CC7)=O)=O)=O)C=C2)O
InChI	InChI=1S/C43H51ClN4O7/c1-43(2,31-5-10-35(11-6-31)55-27-33(49)24-44)30-3-8-34(9-4-30)54-26-29-15-19-46(20-16-29)25-28-17-21-47(22-18-28)32-7-12-36-37(23-32)42(53)48(41(36)52)38-13-14-39(50)45-40(38)51/h3-12,23,28-29,33,38,49H,13-22,24-27H2,1-2H3,(H,45,50,51)/t33-,38?/m1/s1
InChI Key	MYCPBYLZNZTLBC-OVFDOZPJSA-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/)