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Human Metabolome Database Version 3.5

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Showing metabocard for Cysteineglutathione disulfide (HMDB00656)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:02 -0700
HMDB ID HMDB00656
Secondary Accession Numbers None
Metabolite Identification
Common Name Cysteineglutathione disulfide
Description Cysteineglutathione 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 Link_out). S-sulfonation and S-thiolation of transthyretin Phe33Cys has been detected in a patient with familial transthyretin amyloidosis. (PMID 12876326 Link_out). 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 Link_out). Cystinosis is an autosomal recessive disorder caused by an impaired transport of cystine out of lysosomes. (PMID 15042893 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. CYSSG
  2. Cysteine-glutathione disulfide
Chemical Formula C13H22N4O8S2
Average Molecular Weight 426.466
Monoisotopic Molecular Weight 426.08790508
IUPAC Name (2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
Traditional IUPAC Name (2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
CAS Registry Number 13081-14-6
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 Key BNRXZEPOHPEEAS-PPSBICQBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Alpha Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • N Acyl Alpha Amino Acid
  • N Acylglycine
  • N Substituted Alpha Amino Acid
  • Organic Disulfide
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
  • Tricarboxylic Acid Derivative
Direct Parent Peptides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 234 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.48 g/L ALOGPS
LogP -3.86 ALOGPS
LogP -8 ChemAxon
LogS -2.46 ALOGPS
pKa (strongest acidic) 1.39 ChemAxon
pKa (strongest basic) 9.5 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 222.14 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 95.76 ChemAxon
Polarizability 40.45 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022166
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00656 Link_out
Metagene Link HMDB00656 Link_out
METLIN ID 5628 Link_out
PubChem Compound 53477713 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Eriksson, 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. 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 Link_out