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 As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (1997), FDA (1998))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
6873 tolcapone
Synonyms Click here for help
Ro 40-7592 | Ro-407592 | Tasmar®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9679856
Reactome Reaction Reactome logo R-HSA-9679775
Other databases
CAS Registry No. 134308-13-7
ChEMBL Ligand CHEMBL1324
DrugBank Ligand DB00323
DrugCentral Ligand 2697
GtoPdb PubChem SID 178103259
PubChem CID 4659569
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Tolcapone (links to external site)
Cat. No. 5864