talmapimod   Click here for help

GtoPdb Ligand ID: 7817

Synonyms: SCIO 469 hydrochloride | SCIO-469
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Talmapimod is an orally bioavailable, investigational small-molecule p38 mitogen-activated protein kinase (MAPK) inhibitor with potential immunomodulating, anti-inflammatory, and antineoplastic activities.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 65.86
Molecular weight 512.2
XLogP 4.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Fc1ccc(cc1)CN1CC(C)N(CC1C)C(=O)c1cc2c(cn(c2cc1Cl)C)C(=O)C(=O)N(C)C
Isomeric SMILES Fc1ccc(cc1)CN1C[C@@H](C)N(C[C@@H]1C)C(=O)c1cc2c(cn(c2cc1Cl)C)C(=O)C(=O)N(C)C
InChI InChI=1S/C27H30ClFN4O3/c1-16-13-33(17(2)12-32(16)14-18-6-8-19(29)9-7-18)26(35)21-10-20-22(25(34)27(36)30(3)4)15-31(5)24(20)11-23(21)28/h6-11,15-17H,12-14H2,1-5H3/t16-,17+/m0/s1
InChI Key ZMELOYOKMZBMRB-DLBZAZTESA-N
References
1. Tan X, Tester RW, Luedtke GR, Chakravarty S, Mavunkel BJ, Perumattam JJ, Lu Q, Nashashibi I, Jung J, Hu J et al.. (2010)
Design and synthesis of piperazine-indole p38 alpha MAP kinase inhibitors with improved pharmacokinetic profiles.
Bioorg Med Chem Lett, 20 (3): 828-31. [PMID:20071169]