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CHEBI:31539 - epalrestat

ChEBI IDCHEBI:31539
ChEBI Nameepalrestat
Stars
DefinitionA monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-methyl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, including neuropathy.
Last Modified22 February 2017
DownloadsMolfile
FormulaC15H13NO3S2
Net Charge0
Average Mass319.407
Monoisotopic Mass319.03369
SMILESCC(/C=C1\SC(=S)N(CC(=O)O)C1=O)=C\c1ccccc1
InChIInChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8-
InChIKeyCHNUOJQWGUIOLD-NFZZJPOKSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
EC 1.1.1.21 (aldehyde reductase) inhibitor  An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
ChEBI Ontology
Outgoing Relation(s)
epalrestat (CHEBI:31539) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
epalrestat (CHEBI:31539) is a monocarboxylic acid (CHEBI:25384)
epalrestat (CHEBI:31539) is a thiazolidines (CHEBI:35622)
IUPAC Name 
{(5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid
INNs  Source
epalrestatWHO MedNet
epalrestatumChemIDplus
epalrestatChemIDplus
épalrestatWHO MedNet
Synonyms  Source
5-((1Z,2E)-2-methyl-3-phenylpropenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acidChemIDplus
5-((Z,E)-β-methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acidChemIDplus
Ono 2235ChemIDplus
ONO-2235ChEBI
ONO-2ChEBI
ONO 2ChEBI
Brand Name  Source
KinedakKEGG DRUG
Manual XrefsDatabases
D01688KEGG DRUG
EpalrestatWikipedia
EPRPDBeChem
EP47109Patent
US4464382Patent
1021DrugCentral
Registry NumbersSources
Reaxys:4236712Reaxys
CAS:82159-09-9ChemIDplus
Citations