Showing metabocard for Cysteineglutathione disulfide (BMDB0000656)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:23 UTC
Update Date2020-05-11 20:37:29 UTC
BMDB IDBMDB0000656
Secondary Accession Numbers
  • BMDB00656
Metabolite Identification
Common NameCysteineglutathione disulfide
DescriptionCysteineglutathione disulfide, also known as CYSSG or nereithione, 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. Based on a literature review a significant number of articles have been published on Cysteineglutathione disulfide.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.76 m³·mol⁻¹ChemAxon
Polarizability40.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000656
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
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 ReferencesNot Available