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 As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
InChI Key MIQPIUSUKVNLNT-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (1997), FDA (1998))
IUPAC Name Click here for help
(3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
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
RCSB PDB Ligand TCW
Search Google for chemical match using the InChIKey MIQPIUSUKVNLNT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MIQPIUSUKVNLNT
Search PubMed clinical trials tolcapone
Search PubMed titles tolcapone
Search PubMed titles/abstracts tolcapone
Search UniChem for chemical match using the InChIKey MIQPIUSUKVNLNT-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone MIQPIUSUKVNLNT
Wikipedia Tolcapone

Product suppliers

View disclaimer

Tocris
Tolcapone
Cat. No. 5864