CHEBI:16163 - S-carboxymethyl-L-cysteine

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ChEBI Name S-carboxymethyl-L-cysteine
ChEBI ID CHEBI:16163
ChEBI ASCII Name S-carboxymethyl-L-cysteine
Definition An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41438, CHEBI:8954, CHEBI:22040, CHEBI:12745
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Formula C5H9NO4S
Net Charge 0
Average Mass 179.19530
Monoisotopic Mass 179.02523
InChI InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChIKey GBFLZEXEOZUWRN-VKHMYHEASA-N
SMILES N[C@@H](CSCC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing S-carboxymethyl-L-cysteine (CHEBI:16163) has role mucolytic (CHEBI:77034)
S-carboxymethyl-L-cysteine (CHEBI:16163) is a L-cysteine thioether (CHEBI:27532)
S-carboxymethyl-L-cysteine (CHEBI:16163) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
S-carboxymethyl-L-cysteine (CHEBI:16163) is conjugate acid of S-carboxylatomethyl-L-cysteine(1−) (CHEBI:57662)
Incoming S-carboxylatomethyl-L-cysteine(1−) (CHEBI:57662) is conjugate base of S-carboxymethyl-L-cysteine (CHEBI:16163)
IUPAC Names
(2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
S-(carboxymethyl)-L-cysteine
INNs Sources
carbocisteína WHO MedNet
carbocisteine WHO MedNet
carbocistéine WHO MedNet
carbocisteinum WHO MedNet
Synonyms Sources
(L)-2-Amino-3-(carboxymethylthio)propionic acid ChemIDplus
(R)-S-(carboxymethyl)cysteine ChemIDplus
carbocysteine ChemIDplus
L-3-((carboxymethyl)thio)alanine ChemIDplus
L-Carbocisteine KEGG COMPOUND
S-(carboxymethyl)-(R)-cysteine ChemIDplus
S-Carboxymethyl-L-cysteine KEGG COMPOUND
S-carboxymethylcysteine ChEBI
Brand Name Source
Mucodyne KEGG DRUG
Manual Xrefs Databases
4160 DrugCentral
C03727 KEGG COMPOUND
Carbocisteine Wikipedia
CCS PDBeChem
CPD-44 MetaCyc
D00175 KEGG DRUG
HMDB0029415 HMDB
View more database links
Registry Numbers Types Sources
1043764 Gmelin Registry Number Gmelin
1725012 Reaxys Registry Number Reaxys
1725012 Beilstein Registry Number ChemIDplus
638-23-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19126298 PubMed citation Europe PMC
22497630 PubMed citation Europe PMC
23728642 PubMed citation Europe PMC
Last Modified
22 February 2017