| Common Name |
S-Carboxymethyl-L-cysteine
| Description |
S-carboxymethylcysteine (carbocisteine) is the most frequently prescribed mucoactive agent for long-term COPD (chronic obstructive plimonary disease) use in a number of countries. In addition to its mucoregliatory activity, carbocisteine exhibits free-radical scavenging and anti-inflammatory properties. S-Carboxymethyl-L-cysteine can be found in root vegetables and has been isolated from radish seedlings. S-carboxymethyl-L-cysteine can be detectable in urine especially after the processing of chlorinated compounds by gut microlfora.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29415 (S-Carboxymethyl-L-cysteine)
| Synonyms |
| Value |
Source |
CarbocisteineKegg
MucofanKegg
(L)-2-amino-3-(carboxymethylthio)Propionic acidHMDB
(R)-S-(Carboxymethyl)cysteineHMDB
1-CarboxymethylcysteineHMDB
2-amino-3-(carboxymethylthio)Propionic acidHMDB
2-amino-3-[(Carboxymethyl)slifanyl]propanoic acidHMDB
3-((Carboxymethyl)thio)alanineHMDB
3-(carboxymethylthio)-L-AlanineHMDB
3-(carboxymethylthio)AlanineHMDB
3-[(Carboxymethyl)thio]-L-alanineHMDB
3-[(Carboxymethyl)thio]alanineHMDB
5-amino-3-Thiadihexanoic acidHMDB
Carboxymethylated cysteineHMDB
CarboxymethylcysteineHMDB
CarboxymethylenecysteineHMDB
L-3-((Carboxymethyl)thio)alanineHMDB
L-CarboxymethylcysteineHMDB
LoviscolHMDB
MuciclarHMDB
MucocisHMDB
MucodineHMDB
MucodyneHMDB
ReomucilHMDB
RhinathiolHMDB
S-(Carboxymethyl)-(R)-cysteineHMDB
S-(Carboxymethyl)-L-cysteineHMDB
S-(Carboxymethyl)cysteineHMDB
S-Carboxylmethyl-L-cysteineHMDB
S-CarboxymethylcysteineHMDB
ThiodrilHMDB
| Chemical Formlia |
C5H9NO4S
| Average Molecliar Weight |
179.194
| Monoisotopic Molecliar Weight |
179.025228471
| IUPAC Name |
2-amino-3-[(carboxymethyl)slifanyl]propanoic acid
| Traditional Name |
carbocystein
| CAS Registry Number |
2387-59-9
| SMILES |
NC(CSCC(O)=O)C(O)=O
| InChI Identifier |
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)
| InChI Key |
GBFLZEXEOZUWRN-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
| Kingdom |
Organic compounds
| Super Class |
Organic acids and derivatives
| Class |
Carboxylic acids and derivatives
| Sub Class |
Amino acids, peptides, and analogues
| Direct Parent |
Alpha amino acids
| Alternative Parents |
Dicarboxylic acids and derivatives
Slifenyl compounds
Dialkylthioethers
Carboxylic acids
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Alpha-amino acid
Dicarboxylic acid or derivatives
Dialkylthioether
Slifenyl compound
Thioether
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organoslifur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point204 – 207 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility21.6 mg/mLALOGPS
logP-3.2ALOGPS
logP-3.3ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.11 m3·mol-1ChemAxon
Polarizability16.66 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000507
| KNApSAcK ID |
Not Available
| Chemspider ID |
1050
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29415
| Metagene Link |
HMDB29415
| METLIN ID |
Not Available
| PubChem Compound |
1080
| PDB ID |
Not Available
| ChEBI ID |
971853
Product: LY3039478
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 23776692
