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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:13 UTC
HMDB IDHMDB0000656
Secondary Accession Numbers
  • HMDB00656
Metabolite Identification
Common NameCysteineglutathione disulfide
DescriptionCysteineglutathione disulfide is a molecule that is formed upon oxidative stress of glutathione, that will form mixed disulfides with protein thiol groups, causing reversible S-glutathionylation. S-glutathionylation is an important post-translational modification responsible for transducing oxidant signals. S-glutathionylation of thiols confers protection against their irreversible oxidation, like for instance the formation of sulphonic acid moieties. If the targeted cysteine is a functionally critical amino acid, S-glutathionylation will however also modify protein function. (PMID 16515838 ). S-sulfonation and S-thiolation of transthyretin Phe33Cys has been detected in a patient with familial transthyretin amyloidosis. (PMID 12876326 ). In Cystinotic human skin fibroblasts in tissue culture there is an accumulation of cystine. Stored cystine in cystinotic tissues may derive in part from glutathione-cysteine mixed disulfide via transpeptidation. (PMID 6130452 ). Cystinosis is an autosomal recessive disorder caused by an impaired transport of cystine out of lysosomes. (PMID 15042893 ).
Structure
Thumb
Synonyms
ValueSource
Cysteineglutathione disulphideGenerator
CYSSGHMDB
Cysteine-glutathione disulfideHMDB
Cysteine-glutathione mixed disulfideHMDB
NereithioneHMDB
(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoateHMDB
(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoateHMDB
(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acidHMDB
Cysteine glutathione disulphideHMDB
Chemical FormulaC13H22N4O8S2
Average Molecular Weight426.466
Monoisotopic Molecular Weight426.08790508
IUPAC Name(2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
Traditional Name(2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
CAS Registry Number13081-14-6
SMILES
N[C@@H](CCC(=O)N[C@@H](CSSCC(N)C(O)=O)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C13H22N4O8S2/c14-6(12(22)23)1-2-9(18)17-8(11(21)16-3-10(19)20)5-27-26-4-7(15)13(24)25/h6-8H,1-5,14-15H2,(H,16,21)(H,17,18)(H,19,20)(H,22,23)(H,24,25)/t6-,7?,8-/m0/s1
InChI KeyBNRXZEPOHPEEAS-PPSBICQBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty amide
  • Fatty acyl
  • Carboxamide group
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxylic acid
  • Sulfenyl compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.227 +/- 0.209 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.234 +/- 0.267 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.362 +/- 1.18 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022166
KNApSAcK IDNot Available
Chemspider ID35013023
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5628
PubChem Compound53477713
PDB IDNot Available
ChEBI ID143243
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceEriksson, Bengt; Eriksson, Stellan A. Synthesis and characterization of the L-cysteine-glutathione mixed disulfide. Acta Chemica Scandinavica (1947-1973) (1967), 21(5), 1304-12.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lim A, Prokaeva T, McComb ME, Connors LH, Skinner M, Costello CE: Identification of S-sulfonation and S-thiolation of a novel transthyretin Phe33Cys variant from a patient diagnosed with familial transthyretin amyloidosis. Protein Sci. 2003 Aug;12(8):1775-85. [PubMed:12876326 ]
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Reynaert NL, Ckless K, Guala AS, Wouters EF, van der Vliet A, Janssen-Heininger YM: In situ detection of S-glutathionylated proteins following glutaredoxin-1 catalyzed cysteine derivatization. Biochim Biophys Acta. 2006 Mar;1760(3):380-7. Epub 2006 Feb 20. [PubMed:16515838 ]
  4. Butler JD, Spielberg SP: Accumulation of cystine from glutathione-cysteine mixed disulfide in cystinotic fibroblasts; blockade by an inhibitor of gamma-glutamyl transpeptidase. Life Sci. 1982 Dec 6;31(23):2563-70. [PubMed:6130452 ]
  5. Levtchenko EN, Wilmer M, de Graaf-Hess AC, van den Heuvel LP, Blom H, Monnens LA: [From gene to disease: cystinosis]. Ned Tijdschr Geneeskd. 2004 Mar 6;148(10):476-8. [PubMed:15042893 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]