S-carboxymethyl-L-cysteine (CHEBI:16163)

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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Definition	An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a carboxymethyl group.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

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 )

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.

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

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

Last Modified

22 February 2017