CHEBI:31539 - epalrestat

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ChEBI Name epalrestat
ChEBI ID CHEBI:31539
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H13NO3S2
Net Charge 0
Average Mass 319.39900
Monoisotopic Mass 319.034
InChI InChI=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-
InChIKey CHNUOJQWGUIOLD-NFZZJPOKSA-N
SMILES C\C(\C=C1/SC(=S)N(CC(O)=O)C1=O)=C/c1ccccc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
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ChEBI Ontology
Outgoing 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 Sources
epalrestat ChemIDplus
épalrestat WHO MedNet
epalrestat WHO MedNet
epalrestatum ChemIDplus
Synonyms Sources
5-((1Z,2E)-2-methyl-3-phenylpropenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid ChemIDplus
5-((Z,E)-β-methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid ChemIDplus
ONO 2 ChEBI
Ono 2235 ChemIDplus
ONO-2 ChEBI
ONO-2235 ChEBI
Brand Name Source
Kinedak KEGG DRUG
Manual Xrefs Databases
1021 DrugCentral
D01688 KEGG DRUG
EP47109 Patent
Epalrestat Wikipedia
EPR PDBeChem
US4464382 Patent
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Registry Numbers Types Sources
4236712 Reaxys Registry Number Reaxys
82159-09-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19716319 PubMed citation Europe PMC
22820572 PubMed citation Europe PMC
23426701 PubMed citation Europe PMC
24363998 PubMed citation Europe PMC
3025043 PubMed citation Europe PMC
Last Modified
22 February 2017