tamibarotene   Click here for help

GtoPdb Ligand ID: 2648

Synonyms: AM-80 | AM80 | Amnolake® | retinobenzoic acid
Approved drug PDB Ligand
tamibarotene is an approved drug
Compound class: Synthetic organic
Comment: This compound is a retinoic acid receptor α (RARα) agonist [3].
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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(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C
Isomeric SMILES O=C(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C
InChI InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
Bioactivity Comments
Tamibarotene (AM 80) induces differentiation and apoptosis of HL-60 cells in vitro. It exhibits antiproliferative effects against a variety of human tumor cells lines and displays anticancer activity against acute promyelocytic leukemia in vivo
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-α Primary target of this compound Hs Agonist Agonist 7.3 pEC50 - 5
pEC50 7.3 (EC50 4.5x10-8 M) [5]
Retinoic acid receptor-β Hs Agonist Agonist 6.6 pEC50 - 5
pEC50 6.6 (EC50 2.35x10-7 M) [5]
Retinoic acid receptor-γ Hs Agonist Agonist 6.2 pEC50 - 5
pEC50 6.2 (EC50 5.91x10-7 M) [5]
Retinoic acid receptor-α Primary target of this compound Hs Agonist Agonist 6.9 pIC50 - 1-2,4
pIC50 6.9 [1-2,4]