Ro 40-6055   Click here for help

GtoPdb Ligand ID: 2647

Synonyms: AM 580 | AM580 | CD-336 | Ro406055
PDB Ligand
Compound class: Synthetic organic
Comment: Ro 40-6055 (Am580) is a retinoic acid analogue that acts as a selective retinoic acid receptor α (RARα) agonist [1].
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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 4
Topological polar surface area 66.4
Molecular weight 351.18
XLogP 5.9
No. Lipinski's rules broken 1
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Canonical SMILES O=C(c1ccc2c(c1)C(C)(C)CCC2(C)C)Nc1ccc(cc1)C(=O)O
Isomeric SMILES O=C(c1ccc2c(c1)C(C)(C)CCC2(C)C)Nc1ccc(cc1)C(=O)O
InChI InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
1. Charton J, Deprez-Poulain R, Hennuyer N, Tailleux A, Staels B, Deprez B. (2009)
Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.
Bioorg Med Chem Lett, 19 (2): 489-92. [PMID:19058965]
2. Delescluse C, Cavey MT, Martin B, Bernard BA, Reichert U, Maignan J, Darmon M, Shroot B. (1991)
Selective high affinity retinoic acid receptor alpha or beta-gamma ligands.
Mol Pharmacol, 40 (4): 556-62. [PMID:1656191]
3. Wang W, Yang J, Liu H, Lu D, Chen X, Zenonos Z, Campos LS, Rad R, Guo G, Zhang S et al.. (2011)
Rapid and efficient reprogramming of somatic cells to induced pluripotent stem cells by retinoic acid receptor gamma and liver receptor homolog 1.
Proc Natl Acad Sci USA, 108 (45): 18283-8. [PMID:21990348]