tolcapone   Click here for help

GtoPdb Ligand ID: 6646

Synonyms: Ro 40-7592 | Ro-407592 | Tasmar®
Approved drug PDB Ligand
tolcapone is an approved drug (EMA (1997), FDA (1998))
Compound class: Synthetic organic
Comment: Tolcapone is a selective, potent and reversible nitro catechol type inhibitor of enzyme catechol-O-methyl transferase (COMT). As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 100.67
Molecular weight 273.06
XLogP 4.11
No. Lipinski's rules broken 0
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Canonical SMILES Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
Isomeric SMILES Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
InChI InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
1. Lotta T, Vidgren J, Tilgmann C, Ulmanen I, Melén K, Julkunen I, Taskinen J. (1995)
Kinetics of human soluble and membrane-bound catechol O-methyltransferase: a revised mechanism and description of the thermolabile variant of the enzyme.
Biochemistry, 34 (13): 4202-10. [PMID:7703232]