BMS-189532   Click here for help

GtoPdb Ligand ID: 11955

Synonyms: AGN-193491 | BMS189532 | compound 2 [PMID: 24040487]
Compound class: Synthetic organic
Comment: BMS-189532 is a retinoic acid receptor-α (RAR-α) selective antagonist, that was designed for activity as a non-hormonal male contraceptive [1-2]. Antagonising RAR-α is predicted to disrupt spermatogenesis. Despite potent antagonism of RAR-α in vitro, the compound was ineffective in vivo by oral administration. A modified chemotype with the expected in vivo effect on sperm development is represented by YCT529.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 66.4
Molecular weight 411.18
XLogP 7.17
No. Lipinski's rules broken 1
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Canonical SMILES Cc1ccc(cc1)C1=CCC(c2c1cc(cc2)C(=O)Nc1ccc(cc1)C(=O)O)(C)C
Isomeric SMILES Cc1ccc(cc1)C1=CCC(C)(C)c2c1cc(cc2)C(=O)Nc1ccc(cc1)C(=O)O
InChI InChI=1S/C27H25NO3/c1-17-4-6-18(7-5-17)22-14-15-27(2,3)24-13-10-20(16-23(22)24)25(29)28-21-11-8-19(9-12-21)26(30)31/h4-14,16H,15H2,1-3H3,(H,28,29)(H,30,31)