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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1324
CHEMBL1324
Compound Name TOLCAPONE
ChEMBL Synonyms Ro-40-7592 | TASMAR | RO 40-7592 | TOLCAPONE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names TASMAR
Molecular Formula C14H11NO5

Additional synonyms for CHEMBL1324 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1ccc(cc1)C(=O)c2cc(O)c(O)c(c2)[N+](=O)[O-]
Standard InChI InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)1 ...
Download InChI
Standard InChI Key MIQPIUSUKVNLNT-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL1324

Molecule Features

CHEMBL1324 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Withdrawal Information

Year 1998
Country European Union; Canada; Ireland; Portugal; Australia
Reason Hepatotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Catechol O-methyltransferase inhibitor Catechol O-methyltransferase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
PARKINSON DISEASED010300EFO:0002508PARKINSON'S DISEASE4ClinicalTrials
ATC
TOBACCO USE DISORDERD014029EFO:0003768NICOTINE DEPENDENCE2ClinicalTrials
ALCOHOLISMD000437EFO:0003829ALCOHOL DEPENDENCE2ClinicalTrials
GAMBLINGD005715EFO:0004699GAMBLING BEHAVIOUR2ClinicalTrials
PICK DISEASE OF THE BRAIND020774EFO:0003096PICK DISEASE2ClinicalTrials

Clinical Data

ClinicalTrials.gov TOLCAPONE
The Cochrane Collaboration TOLCAPONE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1324. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 1.000
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 1.000
CHEMBL2789 Estradiol 17-beta-dehydrogenase 2 Homo sapiens 0.998
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.998
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.996
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.996
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 0.994
CHEMBL2392 DNA polymerase beta Homo sapiens 0.994
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.980
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.975
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.966
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.954
CHEMBL5514 Huntingtin Homo sapiens 0.945
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.934
CHEMBL4421 HM74 nicotinic acid GPCR Homo sapiens 0.898
CHEMBL2623 Acyl coenzyme A:cholesterol acyltransferase Oryctolagus cuniculus 0.889
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.888
CHEMBL1163101 Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens 0.875
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.849
CHEMBL3180 Carboxylesterase 2 Homo sapiens 0.832



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2372 Catechol O-methyltransferase Rattus norvegicus 1.000
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 1.000
CHEMBL1293267 G-protein coupled receptor 35 Homo sapiens 1.000
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 1.000
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.998
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.995
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.991
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.990
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.989
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.982
CHEMBL5514 Huntingtin Homo sapiens 0.981
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.973
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.961
CHEMBL2392 DNA polymerase beta Homo sapiens 0.956
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.951
CHEMBL5847 Aldo-keto reductase family 1 member C2 Homo sapiens 0.950
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 0.936
CHEMBL4143 Calpain 2 Sus scrofa 0.919
CHEMBL3475 Plasminogen activator inhibitor-1 Homo sapiens 0.900
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.873

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
273.2 273.0637 3.13 3 103.35 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.78 - 3.02 .76 2 20 0.39

Structural Alerts

There are 7 structural alerts for CHEMBL1324. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N04 - ANTI-PARKINSON DRUGS
N04B - DOPAMINERGIC AGENTS
N04BX - Other dopaminergic agents
N04BX01 - tolcapone

ChemSpider ChemSpider:MIQPIUSUKVNLNT-UHFFFAOYSA-N
DailyMed tolcapone
PubChem SID: 144206516 SID: 144212731 SID: 170465081 SID: 50126317
Wikipedia Tolcapone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1324



ACToR 134308-13-7
BindingDB 50108877
Brenda 23408
ChEBI 63630
DrugBank DB00323
DrugCentral 2697
eMolecules 2735694
EPA CompTox Dashboard DTXSID3023685
FDA SRS CIF6334OLY
Guide to Pharmacology 6646
Human Metabolome Database HMDB0014468
IBM Patent System A21808BAEF69015996FDECECA6FFADA6
KEGG Ligand C07949
LINCS LSM-5282
MolPort MolPort-003-850-570
NMRShiftDB 10021705
PDBe TCW
PharmGKB PA451720
PubChem 4659569
PubChem: Drugs of the Future 12014507
PubChem: Thomson Pharma 15221967
Selleck tolcapone
SureChEMBL SCHEMBL33869
ZINC ZINC000035342789

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/MIQPIUSUKVNLNT-UHFFFAOYSA-N spacer
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