You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:09 UTC
HMDB IDHMDB00656
Secondary Accession NumbersNone
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
CYSSGHMDB
Cysteine-glutathione disulfideHMDB
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 KeyInChIKey=BNRXZEPOHPEEAS-PPSBICQBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl peptides. These are oligo- and polypeptides consisting of any C-terminal alpha peptide having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl peptides
Alternative Parents
Substituents
  • Gamma-glutamyl alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Dialkyldisulfide
  • Secondary carboxylic acid amide
  • Organic disulfide
  • Carboxamide group
  • Sulfenyl compound
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.48 mg/mLALOGPS
logP-3.9ALOGPS
logP-8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area222.14 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.76 m3·mol-1ChemAxon
Polarizability40.45 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0390100000-5fa8a02559e5d3e0f3d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01t9-1910000000-7ca978670daa10642074View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00e9-1972100000-95e2b60e54e43eab9368View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022166
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00656
Metagene LinkHMDB00656
METLIN ID5628
PubChem Compound53477713
PDB IDNot Available
ChEBI 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)Download (PDF)
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. [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. [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. [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. [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. [15042893 ]