CHEBI:41531 - methyl L-cysteinate

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ChEBI Name methyl L-cysteinate
ChEBI ID CHEBI:41531
ChEBI ASCII Name methyl L-cysteinate
Definition An L-cysteinyl ester resulting from the formal condensation of the carboxylic acid group of L-cysteine with methanol. It is used (as the hydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive cough.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C4H9NO2S
Net Charge 0
Average Mass 135.18500
Monoisotopic Mass 135.03540
InChI InChI=1S/C4H9NO2S/c1-7-4(6)3(5)2-8/h3,8H,2,5H2,1H3/t3-/m0/s1
InChIKey MCYHPZGUONZRGO-VKHMYHEASA-N
SMILES COC(=O)[C@@H](N)CS
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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 methyl L-cysteinate (CHEBI:41531) has functional parent L-cysteine (CHEBI:17561)
methyl L-cysteinate (CHEBI:41531) has functional parent methanol (CHEBI:17790)
methyl L-cysteinate (CHEBI:41531) has role mucolytic (CHEBI:77034)
methyl L-cysteinate (CHEBI:41531) is a L-cysteinyl ester (CHEBI:61894)
methyl L-cysteinate (CHEBI:41531) is a primary amino compound (CHEBI:50994)
methyl L-cysteinate (CHEBI:41531) is a thiol (CHEBI:29256)
Incoming methyl L-cysteinato group (CHEBI:61989) is substituent group from methyl L-cysteinate (CHEBI:41531)
IUPAC Name
methyl L-cysteinate
INNs Sources
mecisteína WHO MedNet
mecysteine ChemIDplus
mécystéine WHO MedNet
mecysteinum ChemIDplus
Synonyms Sources
cysteine methyl ester ChemIDplus
methyl (R)-cysteinate ChemIDplus
O-METHYLCYSTEINE PDBeChem
Manual Xrefs Databases
1653 DrugCentral
CMT PDBeChem
D08164 KEGG DRUG
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Registry Numbers Types Sources
1721306 Reaxys Registry Number Reaxys
2485-62-3 CAS Registry Number KEGG DRUG
2485-62-3 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
16027914 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-04-18 The hydrochloride salt of methyl L-cysteinate is used as a mucolytic for the treatment of respiratory disorders associated with productive coughs (i.e. coughs associated with the production of sputum).