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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:30:17 UTC
Update Date2021-09-14 15:00:47 UTC
HMDB IDHMDB0029415
Secondary Accession Numbers
  • HMDB29415
Metabolite Identification
Common NameS-Carboxymethyl-L-cysteine
DescriptionS-carboxymethylcysteine (carbocisteine) is the most frequently prescribed mucoactive agent for long-term COPD (chronic obstructive pulmonary disease) use in a number of countries. In addition to its mucoregulatory 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
Data?1582753415
Synonyms
ValueSource
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)sulfanyl]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
Carbocysteine, L-isomerHMDB
S CarboxymethylcysteineHMDB
MukodinHMDB
Carbocysteine, L isomerHMDB
L-Isomer carbocysteineHMDB
Chemical FormulaC5H9NO4S
Average Molecular Weight179.194
Monoisotopic Molecular Weight179.025228471
IUPAC Name2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
Traditional Namecarbocystein
CAS Registry Number2387-59-9
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 KeyGBFLZEXEOZUWRN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 - 207 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+Baker141.13330932474
DeepCCS[M+H]+MetCCS_train_pos137.18530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility21.6 g/LALOGPS
logP10(-3.2) g/LALOGPS
logP10(-3.3) g/LChemAxon
logS10(-0.92) g/LALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.11 m³·mol⁻¹ChemAxon
Polarizability16.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.61931661259
DarkChem[M-H]-132.47631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
S-Carboxymethyl-L-cysteine,1TMS,#1C[Si](C)(C)OC(=O)CSCC(N)C(=O)O1716.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,1TMS,#2C[Si](C)(C)OC(=O)C(N)CSCC(=O)O1758.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,1TMS,#3C[Si](C)(C)NC(CSCC(=O)O)C(=O)O1793.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TMS,#1C[Si](C)(C)OC(=O)CSCC(N)C(=O)O[Si](C)(C)C1755.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TMS,#2C[Si](C)(C)NC(CSCC(=O)O[Si](C)(C)C)C(=O)O1836.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TMS,#3C[Si](C)(C)NC(CSCC(=O)O)C(=O)O[Si](C)(C)C1828.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TMS,#4C[Si](C)(C)N(C(CSCC(=O)O)C(=O)O)[Si](C)(C)C1980.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CSCC(N)C(=O)O1977.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)C(N)CSCC(=O)O2006.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,1TBDMS,#3CC(C)(C)[Si](C)(C)NC(CSCC(=O)O)C(=O)O2038.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CSCC(N)C(=O)O[Si](C)(C)C(C)(C)C2206.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TBDMS,#2CC(C)(C)[Si](C)(C)NC(CSCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2299.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TBDMS,#3CC(C)(C)[Si](C)(C)NC(CSCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2290.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
S-Carboxymethyl-L-cysteine,2TBDMS,#4CC(C)(C)[Si](C)(C)N(C(CSCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C2415.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-EI-TOF (Non-derivatized)splash10-05mk-1920000000-1bfde05bf74ad952988c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-EI-TOF (Non-derivatized)splash10-0gba-0950000000-3deefa0cf048f58da5b72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-EI-TOF (Non-derivatized)splash10-05mk-1920000000-1bfde05bf74ad952988c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-EI-TOF (Non-derivatized)splash10-0gba-0950000000-3deefa0cf048f58da5b72018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-c20980f00a00f1e6e1802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-MS (2 TMS) - 70eV, Positivesplash10-05g4-9650000000-0aed012631a77de5b93a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Carboxymethyl-L-cysteine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 10V, Positive-QTOFsplash10-001i-3900000000-33a818ac062af18410a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 20V, Positive-QTOFsplash10-000x-9500000000-c7b2a3062072d67fbc4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 40V, Positive-QTOFsplash10-00du-9100000000-0e0a6581889fafc8e6d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 10V, Negative-QTOFsplash10-004l-6900000000-ee309c95fd84852db4572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 20V, Negative-QTOFsplash10-0006-9200000000-396c0c726a8b135b8da42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 40V, Negative-QTOFsplash10-000f-9000000000-5243edfeeee8b8e7df3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 10V, Negative-QTOFsplash10-0006-9000000000-2205efc680b90ef8e86d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 20V, Negative-QTOFsplash10-0005-9000000000-c2902dceba4c5c4564232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 40V, Negative-QTOFsplash10-0005-9000000000-95016c8505c678c2d2ef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 10V, Positive-QTOFsplash10-00kf-8900000000-5572c3ac9193ded608722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 20V, Positive-QTOFsplash10-0079-9100000000-f93524089b1962d1a05c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Carboxymethyl-L-cysteine 40V, Positive-QTOFsplash10-00dl-9000000000-3faa3225eb48986452402021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000507
KNApSAcK IDNot Available
Chemspider ID1050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbocisteine
METLIN IDNot Available
PubChem Compound1080
PDB IDNot Available
ChEBI ID971853
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .