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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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)
1. Chung SS, Cuellar RA, Wang X, Reczek PR, Georg GI, Wolgemuth DJ. (2013)
Pharmacological activity of retinoic acid receptor alpha-selective antagonists in vitro and in vivo..
ACS Med Chem Lett, 4 (5): 446-450. [PMID:24040487]
2. Noman MAA, Kyzer JL, Chung SSW, Wolgemuth DJ, Georg GI. (2020)
Retinoic acid receptor antagonists for male contraception: current status†.
Biol Reprod, 103 (2): 390-399. [PMID:32671394]
3. Teng M, Duong TT, Johnson AT, Klein ES, Wang L, Khalifa B, Chandraratna RA. (1997)
Identification of highly potent retinoic acid receptor alpha-selective antagonists.
J Med Chem, 40 (16): 2445-51. [PMID:9258350]