CHEBI:88271 - letosteine

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ChEBI Name letosteine
ChEBI ID CHEBI:88271
Definition A dicarboxylic acid monoester that is the monoethyl ester of 2-{2-[(carboxymethyl)sulfanyl]ethyl}-1,3-thiazolidine-4-carboxylic acid. A mucolytic used in the treatment of chronic bronchopneumopathies and related conditions.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H17NO4S2
Net Charge 0
Average Mass 279.379
Monoisotopic Mass 279.05990
InChI InChI=1S/C10H17NO4S2/c1-2-15-9(12)6-16-4-3-8-11-7(5-17-8)10(13)14/h7-8,11H,2-6H2,1H3,(H,13,14)
InChIKey IKOCLISPVJZJEA-UHFFFAOYSA-N
SMILES S1C(NC(C1)C(=O)O)CCSCC(OCC)=O
Metabolite of Species Details
Bacillus methanolicus MGA3 (NCBI:txid796606) See: MetaboLights Study
Bacillus methanolicus MGA3 (NCBI:txid796606) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): mucolytic
A compound that alters the structure of mucus so as to decrease its viscosity and thereby facilitate its removal by ciliary action and expectoration. Compare with antitussives, which suppress the cough reflex, and expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing.
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ChEBI Ontology
Outgoing letosteine (CHEBI:88271) has role mucolytic (CHEBI:77034)
letosteine (CHEBI:88271) is a aliphatic sulfide (CHEBI:22327)
letosteine (CHEBI:88271) is a dicarboxylic acid monoester (CHEBI:36244)
letosteine (CHEBI:88271) is a thiazolidinemonocarboxylic acid (CHEBI:48875)
IUPAC Name
2-{2-[(2-ethoxy-2-oxoethyl)sulfanyl]ethyl}-1,3-thiazolidine-4-carboxylic acid
INNs Sources
letosteina ChemIDplus
letosteine ChemIDplus
letosteine KEGG DRUG
letosteinum ChemIDplus
Synonym Source
2-(2-((Carboxymethyl)thio)ethyl)-4-thiazolidinecarboxylic acid 2-ethyl ester ChemIDplus
Manual Xrefs Databases
1555 DrugCentral
D07380 KEGG DRUG
DB08939 DrugBank
Letosteine Wikipedia
US6987120 Patent
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Registry Numbers Types Sources
53943-88-7 CAS Registry Number KEGG DRUG
53943-88-7 CAS Registry Number ChemIDplus
999728 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017