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CHEBI:16163 - S-carboxymethyl-L-cysteine

Default Structure
ChEBI IDCHEBI:16163
ChEBI NameS-carboxymethyl-L-cysteine
Stars
ASCII NameS-carboxymethyl-L-cysteine
DefinitionAn L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.
Secondary ChEBI IDsCHEBI:8954, CHEBI:12745, CHEBI:22040, CHEBI:41438
Last Modified22 February 2017
DownloadsMolfile
FormulaC5H9NO4S
Net Charge0
Average Mass179.197
Monoisotopic Mass179.02523
SMILESN[C@@H](CSCC(=O)O)C(=O)O
InChIInChI=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
InChIKeyGBFLZEXEOZUWRN-VKHMYHEASA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
carbocisteínaWHO MedNet
carbocisteineWHO MedNet
carbocistéineWHO MedNet
carbocisteinumWHO MedNet
Synonyms  Source
carbocysteineChemIDplus
S-carboxymethylcysteineChEBI
S-(carboxymethyl)-(R)-cysteineChemIDplus
(R)-S-(carboxymethyl)cysteineChemIDplus
(L)-2-Amino-3-(carboxymethylthio)propionic acidChemIDplus
L-CarbocisteineKEGG COMPOUND
Brand Name  Source
MucodyneKEGG DRUG
Manual XrefsDatabases
4160DrugCentral
C03727KEGG COMPOUND
CarbocisteineWikipedia
CCSPDBeChem
CPD-44MetaCyc
D00175KEGG DRUG
HMDB0029415HMDB
Registry NumbersSources
Gmelin:1043764Gmelin
Reaxys:1725012Reaxys
CAS:638-23-3KEGG COMPOUND
CAS:638-23-3ChemIDplus
Citations