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S-Carboxymethyl-L-cysteine (M2MDB003492)

Record Information
Version2.0
Creation Date2012-10-10 12:16:46 -0600
Update Date2015-06-03 17:25:56 -0600
Secondary Accession Numbers
  • ECMDB23102
Identification
Name:S-Carboxymethyl-L-cysteine
DescriptionS-Carboxymethyl-L-cysteine is the side-chain carboxymethyl derivative of cysteine. It is produced during the metabolism of 3-chloro-L-alanine via the enzyme Cysteine synthase A. The reaction is 3-chloro-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R)-2-amino-3-(Carboxymethylsulfanyl)propanoate
  • (2R)-2-amino-3-(carboxymethylsulfanyl)propanoic acid
  • (2R)-2-amino-3-(Carboxymethylsulphanyl)propanoate
  • (2R)-2-amino-3-(Carboxymethylsulphanyl)propanoic acid
  • (L)-2-amino-3-(carboxymethylthio)Propionate
  • (L)-2-Amino-3-(carboxymethylthio)propionic acid
  • (R)-S-(carboxymethyl)cysteine
  • 1-Carboxymethylcysteine
  • 2-amino-3-(carboxymethylthio)Propionate
  • 2-Amino-3-(carboxymethylthio)propionic acid
  • 2-amino-3-[(Carboxymethyl)sulfanyl]propanoate
  • 2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
  • 2-amino-3-[(Carboxymethyl)sulphanyl]propanoate
  • 2-amino-3-[(Carboxymethyl)sulphanyl]propanoic acid
  • 3-((Carboxymethyl)thio)alanine
  • 3-(Carboxymethylthio)-L-alanine
  • 3-(Carboxymethylthio)alanine
  • 3-[(Carboxymethyl)thio]-L-alanine
  • 3-[(Carboxymethyl)thio]alanine
  • 5-amino-3-Thiadihexanoate
  • 5-Amino-3-thiadihexanoic acid
  • Carbocisteine
  • Carbocysteine
  • Carboxymethylated cysteine
  • Carboxymethylcysteine
  • Carboxymethylenecysteine
  • L-3-((carboxymethyl)thio)alanine
  • L-Carbocisteine
  • L-Carboxymethylcysteine
  • L-form
  • Loviscol
  • Muciclar
  • Mucocis
  • Mucodine
  • Mucodyne
  • Mucofan
  • Reomucil
  • Rhinathiol
  • S-(carboxymethyl)-(R)-cysteine
  • S-(carboxymethyl)-L-cysteine
  • S-(Carboxymethyl)cysteine
  • S-Carboxylmethyl-L-cysteine
  • S-Carboxymethylcysteine
  • S-Carboxymethylcysteine, 9CI
  • Thiodril
Chemical Formula:C5H9NO4S
Weight:Average: 179.194
Monoisotopic: 179.025228471
InChI Key:GBFLZEXEOZUWRN-VKHMYHEASA-N
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
CAS number:2387-59-9
IUPAC Name:(2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
Traditional IUPAC Name:carbocisteine
SMILES:N[C@@H](CSCC(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-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
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:204 - 207 C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility21.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.11 m³·mol⁻¹ChemAxon
Polarizability16.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-chloro-D-alanine + Thioglycolate > S-Carboxymethyl-L-cysteine + Chloride
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9530000000-8e6125018eb1d194853bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-4900000000-be70a21dba38823e65e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-4938b5336a3e3dd8ef9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-2e03758abd92fb012326View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-14a74cb7928bcc5929f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-9000000000-c17875b6b7ae40cc59f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-9000000000-c4d5bc66488a8c749f2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-a9d785fbb33e2697f96aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-2819ca720ebc627de3cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ir9-9400000000-4b365357562747ccc151View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0229-9000000000-dd36050965c88158d31bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-9000000000-dc423269c034eeee7369View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01p9-9800000000-667bc6a74e6ab57aec38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01p9-4900000000-643ad96ca5ded235eff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-2900000000-3125c68407eed34d9654View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9500000000-ae4a2feb1a0541a5f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9100000000-611fe19d8bc07f2ccc36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01tc-4900000000-ea145a8cbe7b28667330View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-3da087ea0d68c7cacd26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-9000000000-c648cd0af81d99915af5View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16163
HMDB IDHMDB29415
Pubchem Compound ID193653
Kegg IDC03727
ChemSpider IDNot Available
Wikipedia IDCarbocisteine
BioCyc IDNot Available
Ligand ExpoCCS

Enzymes

Protein Details
1. Cysteine synthase A
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
cysK
Uniprot ID:
P0ABK5
Molecular weight:
34489
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.