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Record Information
Version2.0
Creation Date2012-05-31 14:53:00 -0600
Update Date2015-06-03 17:20:22 -0600
Secondary Accession Numbers
  • ECMDB20604
Identification
Name:S-Carboxymethyl-D-cysteine
DescriptionS-carboxymethyl-D-cysteine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). S-carboxymethyl-D-cysteine is a product of the reaction of D-cysteine desulfhydraase with chloro-D-alanine, which is part of the chloro-alanine degradation process. D-Cysteine desulfhydrase also catalyzes the beta-replacement reaction of the chlorine of 3-chloro-D-alanine with thioglycolic acid to yield S-carboxymethyl-D-cysteine [PMID:3908101]
Structure
Thumb
Synonyms:
  • Carboxymethyl-D-cysteine
Chemical Formula:C5H8NO4S
Weight:Average: 178.186
Monoisotopic: 178.017403439
InChI Key:GBFLZEXEOZUWRN-UHFFFAOYSA-M
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)/p-1
CAS number:Not Available
IUPAC Name:2-[(2-amino-2-carboxyethyl)sulfanyl]acetate
Traditional IUPAC Name:2-[(2-amino-2-carboxyethyl)sulfanyl]acetate
SMILES:NC(CSCC([O-])=O)C(O)=O
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
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility49.1 g/LALOGPS
logP-2.9ALOGPS
logP-3.3ChemAxon
logS-0.6ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.94 m³·mol⁻¹ChemAxon
Polarizability16.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-97c1808452dabac9d45bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ou-5900000000-5f418771d084636a4848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-a8834760ce2717db4803View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-c8600d826b52d3d54763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmr-5900000000-fb5ee5b56cb305fa5d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-31faec85758fee52e5bdView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25203751
Kegg IDNot Available
ChemSpider ID14489359
Wikipedia IDNot Available
BioCyc IDS-CARBOXYMETHYL-D-CYSTEINE
EcoCyc IDS-CARBOXYMETHYL-D-CYSTEINE

Enzymes

General function:
Involved in D-cysteine desulfhydrase activity
Specific function:
Catalyzes the alpha,beta-elimination reaction of D- cysteine and of several D-cysteine derivatives. It could be a defense mechanism against D-cysteine. Can also catalyze the degradation of 3-chloro-D-alanine
Gene Name:
dcyD
Uniprot ID:
P76316
Molecular weight:
35153
Reactions
D-cysteine + H(2)O = H(2)S + NH(3) + pyruvate.