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Record Information
Version1.0
Creation Date2016-09-30 23:03:47 UTC
Update Date2020-05-21 16:28:25 UTC
BMDB IDBMDB0003337
Secondary Accession Numbers
  • BMDB03337
Metabolite Identification
Common NameOxidized glutathione
DescriptionOxidized glutathione, also known as glutathione disulfide or GSSG, 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. Oxidized glutathione is a very strong basic compound (based on its pKa). Oxidized glutathione exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Azaniumyl-4-{[(1R)-2-{[(2R)-2-[(4S)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoateHMDB
Glutathione disulfideHMDB
GSSGHMDB
L(-)-Glutathione(oxidized)HMDB
OxiglutationeHMDB
Chemical FormulaC20H32N6O12S2
Average Molecular Weight612.631
Monoisotopic Molecular Weight612.151961898
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number27025-41-8
SMILESNot Available
InChI Identifier
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)
InChI KeyYPZRWBKMTBYPTK-UHFFFAOYSA-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
  • Tetracarboxylic acid or derivatives
  • 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
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Dialkyldisulfide
  • Secondary carboxylic acid amide
  • Organic disulfide
  • Sulfenyl compound
  • Carboxylic acid
  • Organopnictogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Leukocyte
  • Liver
  • Pancreas
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003337
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023147
KNApSAcK IDNot Available
Chemspider ID950
KEGG Compound IDC00127
BioCyc IDNot Available
BiGG ID33951
Wikipedia LinkGlutathione disulfide
METLIN ID6893
PubChem Compound975
PDB IDNot Available
ChEBI ID17858
References
Synthesis ReferenceSaito, Susumu; Nishijima, Kunihide; Kataoka, Katsuyuki; Aoyanagi, Yoshinori; Fukuda, Yoji; Ito, Homare. Manufacture of oxidized glutathione from reduced glutathione with ascorbic acid and ascorbate oxidase. Jpn. Kokai Tokkyo Koho (1995), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Involved in the control of reactive oxygen species levels and the regulation of mitochondrial redox homeostasis (By similarity). Maintains thioredoxin in a reduced state. May play a role in redox-regulated cell signaling.
Gene Name:
TXNRD2
Uniprot ID:
Q9N2I8
Molecular weight:
54670.0
Reactions
Oxidized glutathione + NADPH →2 Glutathione + NADPdetails
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Essential antioxidant peroxidase that directly reduces phospholipid hydroperoxide even if they are incorporated in membranes and lipoproteins (By similarity). Can also reduce fatty acid hydroperoxide, cholesterol hydroperoxide and thymine hydroperoxide (By similarity). Plays a key role in protecting cells from oxidative damage by preventing membrane lipid peroxidation. Required to prevent cells from ferroptosis, a non-apoptotic cell death resulting from an iron-dependent accumulation of lipid reactive oxygen species. The presence of selenocysteine (Sec) versus Cys at the active site is essential for life: it provides resistance to overoxidation and prevents cells against ferroptosis. The presence of Sec at the active site is also essential for the survival of a specific type of parvalbumin-positive interneurons, thereby preventing against fatal epileptic seizures. May be required to protect cells from the toxicity of ingested lipid hydroperoxides. Required for normal sperm development and male fertility. Essential for maturation and survival of photoreceptor cells. Plays a role in a primary T-cell response to viral and parasitic infection by protecting T-cells from ferroptosis and by supporting T-cell expansion (By similarity).
Gene Name:
GPX4
Uniprot ID:
Q9N2J2
Molecular weight:
22240.0
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P00435
Molecular weight:
22659.0
Reactions
2 Glutathione + Hydrogen peroxide → Oxidized glutathione +2 Waterdetails
15(S)-HPETE + 2 Glutathione → 15(S)-HETE + Oxidized glutathione + Waterdetails
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Possesses significant protein thiol-disulfide oxidase activity.
Gene Name:
TXNDC12
Uniprot ID:
Q5E936
Molecular weight:
19222.0