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 As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

tolcapone is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
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
UniChem Compound Search for chemical match using the InChIKey MIQPIUSUKVNLNT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MIQPIUSUKVNLNT-UHFFFAOYSA-N
Wikipedia Tolcapone

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Tocris
Tolcapone (links to external site)
Cat. No. 5864