ARD-69   

GtoPdb Ligand ID: 10182

Synonyms: ARD69 | compound 34 [PMID: 30629437]
Compound class: Synthetic organic
Comment: ARD-69 is a potent proteolysis-targeting chimera (PROTAC) degrader of the androgen receptor (AR) that was designed as a proof-of-concept lead to evaluate the potential of PROTAC technology as a novel treatment mechanism for AR-positive, castration-resistant prostate cancer [2]. It contains an AR antagonist (reported in [1]) that binds the AR, joined by a small linker molecule to a second ligand (in this case a VHL ligand) that engages the E3 ubiquitin ligase system via Cullin-2. This chimeric molecular structure targets AR protein for ubiquitination-dependent proteolysis.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 225.54
Molecular weight 1128.51
XLogP 8.33
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1ccc(cc1Cl)OC1C(C)(C)C(C1(C)C)NC(=O)c1ccc(cc1)C#CC1CCN(CC1)C1CCN(CC1)C(=O)CC(c1ccc(cc1)c1scnc1C)NC(=O)C1CC(CN1C(=O)C(C(C)(C)C)NC(=O)C1(F)CC1)O
Isomeric SMILES N#Cc1ccc(cc1Cl)O[C@@H]1C(C)(C)[C@H](C1(C)C)NC(=O)c1ccc(cc1)C#CC1CCN(CC1)C1CCN(CC1)C(=O)C[C@@H](c1ccc(cc1)c1scnc1C)NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](C(C)(C)C)NC(=O)C1(F)CC1)O
InChI InChI=1S/C62H74ClFN8O7S/c1-37-51(80-36-66-37)41-17-15-40(16-18-41)48(67-54(76)49-31-45(73)35-72(49)55(77)52(59(2,3)4)68-58(78)62(64)25-26-62)33-50(74)71-29-23-44(24-30-71)70-27-21-39(22-28-70)10-9-38-11-13-42(14-12-38)53(75)69-56-60(5,6)57(61(56,7)8)79-46-20-19-43(34-65)47(63)32-46/h11-20,32,36,39,44-45,48-49,52,56-57,73H,21-31,33,35H2,1-8H3,(H,67,76)(H,68,78)(H,69,75)/t45-,48+,49+,52-,56-,57-/m1/s1
InChI Key CWGVEMFBQJUWLU-RXFAPWBBSA-N
Classification
Compound class Synthetic organic
Ligand families/groups PROTACs and molecular glues
Synonyms
ARD69 | compound 34 [PMID: 30629437]
Database Links
GtoPdb PubChem SID 381118892
PubChem CID 137321163
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