Np mrd loader

Record Information
Version2.0
Created at2006-08-12 19:06:03 UTC
Updated at2024-09-17 15:44:05 UTC
NP-MRD IDNP0001125
Secondary Accession NumbersNone
Natural Product Identification
Common NameOxidized glutathione
DescriptionOxidized glutathione, also known as glutathione disulfide or GSSG, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by the formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. In humans, oxidized glutathione is involved in the metabolic disorder called leukotriene C4 synthesis deficiency pathway. Outside of the human body, oxidized glutathione has been detected, but not quantified in several different foods, such as leeks, star anises, mamey sapotes, climbing beans, and common persimmons. Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. Glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) Catalyzes the conversion of methylglyoxal and reduced glutathione into S-D-lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) Catalyzes the hydrolysis of S-D-lactoyl-glutathione into glutathione and D-lactate.
Structure
Thumb
Synonyms
ValueSource
Glutathione disulphideChEBI
GSSGChEBI
Oxidised glutathioneChEBI
OXIDIZED glutathione disulfideChEBI
OxiglutationeChEBI
GlutathioneKegg
Glutathione disulfideGenerator
OXIDIZED glutathione disulphideGenerator
Disulfide, glutathioneHMDB
Glutathione, oxidizedHMDB
Glutathione disulfide, ion(1-)HMDB
Glutathione-S-S-glutathioneHMDB
Glutathione-SSGHMDB
Oxidized L-glutathioneHMDB
SelenoglutathioneHMDB
Oxidized glutathioneChEBI
Chemical FormulaC20H32N6O12S2
Average Mass612.6310 Da
Monoisotopic Mass612.15196 Da
IUPAC Name(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
Traditional Nameglutathione disulfide
CAS Registry Number27025-41-8
SMILES
NC(CCC(=O)NC(CSSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Enterococcus faecalisLOTUS Database
Flammulina velutipesLOTUS Database
Mus musculusLOTUS Database
Pseudo-nitzschia multistriataLOTUS Database
Thalassiosira pseudonanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Amino acid or derivatives
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility300200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP-3.6ALOGPS
logP-10ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area317.64 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity136.65 m³·mol⁻¹ChemAxon
Polarizability58.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003337
DrugBank IDDB03310
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023147
KNApSAcK IDNot Available
Chemspider ID58835
KEGG Compound IDC00127
BioCyc IDOXIDIZED-GLUTATHIONE
BiGG IDNot Available
Wikipedia LinkGlutathione disulfide
METLIN IDNot Available
PubChem Compound65359
PDB IDNot Available
ChEBI ID17858
Good Scents IDrw1736991
References
General References
  1. Kondo T, Ohtsuka Y, Shimada M, Kawakami Y, Hiyoshi Y, Tsuji Y, Fujii H, Miwa S: Erythrocyte-oxidized glutathione transport in pyrimidine 5'-nucleotidase deficiency. Am J Hematol. 1987 Sep;26(1):37-45. [PubMed:2888306 ]
  2. Calabrese V, Scapagnini G, Ravagna A, Bella R, Butterfield DA, Calvani M, Pennisi G, Giuffrida Stella AM: Disruption of thiol homeostasis and nitrosative stress in the cerebrospinal fluid of patients with active multiple sclerosis: evidence for a protective role of acetylcarnitine. Neurochem Res. 2003 Sep;28(9):1321-8. [PubMed:12938853 ]
  3. Tauler P, Sureda A, Cases N, Aguilo A, Rodriguez-Marroyo JA, Villa G, Tur JA, Pons A: Increased lymphocyte antioxidant defences in response to exhaustive exercise do not prevent oxidative damage. J Nutr Biochem. 2006 Oct;17(10):665-71. Epub 2005 Nov 28. [PubMed:16481153 ]
  4. Slivka A, Spina MB, Cohen G: Reduced and oxidized glutathione in human and monkey brain. Neurosci Lett. 1987 Feb 10;74(1):112-8. [PubMed:3561870 ]
  5. Aukrust P, Svardal AM, Muller F, Lunden B, Berge RK, Ueland PM, Froland SS: Increased levels of oxidized glutathione in CD4+ lymphocytes associated with disturbed intracellular redox balance in human immunodeficiency virus type 1 infection. Blood. 1995 Jul 1;86(1):258-67. [PubMed:7795231 ]
  6. Sakhi AK, Russnes KM, Smeland S, Blomhoff R, Gundersen TE: Simultaneous quantification of reduced and oxidized glutathione in plasma using a two-dimensional chromatographic system with parallel porous graphitized carbon columns coupled with fluorescence and coulometric electrochemical detection. J Chromatogr A. 2006 Feb 3;1104(1-2):179-89. [PubMed:16376913 ]
  7. Glazyrin AL, Kolesnikov SI, Safronov AYu: Histochemical localization of oxidized glutathione-catalysing enzymes in human term placenta. Histochem J. 1993 Jan;25(1):45-50. [PubMed:8432663 ]
  8. Carru C, Zinellu A, Pes GM, Marongiu G, Tadolini B, Deiana L: Ultrarapid capillary electrophoresis method for the determination of reduced and oxidized glutathione in red blood cells. Electrophoresis. 2002 Jun;23(11):1716-21. [PubMed:12179993 ]
  9. Tohgi H, Abe T, Saheki M, Hamato F, Sasaki K, Takahashi S: Reduced and oxidized forms of glutathione and alpha-tocopherol in the cerebrospinal fluid of parkinsonian patients: comparison between before and after L-dopa treatment. Neurosci Lett. 1995 Jan 16;184(1):21-4. [PubMed:7739798 ]
  10. Yoshida T: Determination of reduced and oxidized glutathione in erythrocytes by high-performance liquid chromatography with ultraviolet absorbance detection. J Chromatogr B Biomed Appl. 1996 Apr 12;678(2):157-64. [PubMed:8738017 ]
  11. Sofic E, Lange KW, Jellinger K, Riederer P: Reduced and oxidized glutathione in the substantia nigra of patients with Parkinson's disease. Neurosci Lett. 1992 Aug 17;142(2):128-30. [PubMed:1454205 ]
  12. Muda P, Kampus P, Zilmer M, Zilmer K, Kairane C, Ristimae T, Fischer K, Teesalu R: Homocysteine and red blood cell glutathione as indices for middle-aged untreated essential hypertension patients. J Hypertens. 2003 Dec;21(12):2329-33. [PubMed:14654754 ]
  13. Satoh T, Yoshioka Y: Contribution of reduced and oxidized glutathione to signals detected by magnetic resonance spectroscopy as indicators of local brain redox state. Neurosci Res. 2006 May;55(1):34-9. Epub 2006 Feb 24. [PubMed:16503064 ]
  14. Srivastava SK, Beutler E: Oxidized glutathione levels in erythrocytes of glucose-6-phosphate-dehydrogenase-deficient subjects. Lancet. 1968 Jul 6;2(7558):23-4. [PubMed:4172687 ]
  15. Board P, Nishida T, Gatmaitan Z, Che M, Arias IM: Erythrocyte membrane transport of glutathione conjugates and oxidized glutathione in the Dubin-Johnson syndrome and in rats with hereditary hyperbilirubinemia. Hepatology. 1992 Apr;15(4):722-5. [PubMed:1551648 ]