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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL436
CHEMBL436
Compound Name TOLRESTAT
ChEMBL Synonyms Alderase | ALREDASE | AY-27,773 | AY-27773 | TOLRESTAT
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names ALREDASE | Alderase
Molecular Formula C16H14F3NO3S

Additional synonyms for CHEMBL436 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1ccc2c(cccc2c1C(F)(F)F)C(=S)N(C)CC(=O)O
Standard InChI InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(1 ...
Download InChI
Standard InChI Key LUBHDINQXIHVLS-UHFFFAOYSA-N

Sources

  • British National Formulary
  • 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  • Withdrawn Drugs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


CHEMBL436

Molecule Features

CHEMBL436 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1996
Country Canada; Italy; Argentina
Reason Hepatic necrosis

Clinical Data

ClinicalTrials.gov TOLRESTAT
The Cochrane Collaboration TOLRESTAT

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 CHEMBL436. 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
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.469

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2622 Aldose reductase Rattus norvegicus 0.360
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.331

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
357.4 357.0646 3.98 6 81.86 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 4 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.49 .63 3.59 -.07 2 24 0.79

Structural Alerts

There are 2 structural alerts for CHEMBL436. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A10 - DRUGS USED IN DIABETES
A10X - OTHER DRUGS USED IN DIABETES
A10XA - Aldose reductase inhibitors
A10XA01 - tolrestat

ChemSpider ChemSpider:LUBHDINQXIHVLS-UHFFFAOYSA-N
PubChem SID: 144206867
Wikipedia Tolrestat

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL436



ACToR 82964-04-3
BindingDB 16314
Brenda 1478
ChEBI 48549
DrugBank DB02383
DrugCentral 2704
EPA CompTox Dashboard DTXSID6048834
FDA SRS 0T93LG5NMK
Guide to Pharmacology 7404
IBM Patent System 1E9F76F2622BFC58433B198D377047CB
KEGG Ligand C01621
MolPort MolPort-006-168-350
Nikkaji J23.281E
PDBe TOL
PubChem 53359
PubChem: Drugs of the Future 12014205
PubChem: Thomson Pharma 14803262
SureChEMBL SCHEMBL49326
ZINC ZINC000003780343

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