Oxiglutatione (CHEM020188)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:53:42 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020188
Identification
Common NameOxiglutatione
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass612.631 g/mol
Monoisotopic Mass612.152 g/mol
CAS Registry Number27025-41-8
IUPAC Name2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
Traditional Nameoxiglutatione
SMILESN[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
InChI IdentifierInChI=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)/t9-,10-,11-,12-/m0/s1
InChI KeyYPZRWBKMTBYPTK-BJDJZHNGSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability58.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-c8147955c6b355f0fc5cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0910000000-3e6195d480fbfe87b449Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2121090000-ae2cd04146f2eea049a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01q3-2111039000-a2c6d786111b549344feSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uki-0290000000-04456f914411a2ecbe4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0039210000-772eee67ad10a2d98fa7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-08fr-1957008000-f8812fd72d475ecd2693Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0000109000-65d563bcfc551b4a7abdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0003309000-7555effd0b74737b9d2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0259201000-2cd328143ce713c285d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05d0-0493000000-93bd088394049a484b9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001r-0190000000-88b871b5a3f668f4b3a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0a59-0019811000-b24651cf6fc55de750b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-053s-0495300000-69ab8e397b7a546ecd3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-053r-0007920000-39da34018ceb610daa32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000009000-9cde769e8905f413f7e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000009000-4e3c9569882ab5507bf2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02na-2011492000-e5bf21a4b84acc1cf18fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9002540000-c313b0aedf04e56ccf77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9012110000-27ec93f3d13ce2136a4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0147096000-d734e389344c1dc9b900Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lxx-1597071000-aba0237f549185706415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9501140000-204a269186f92e44ac10Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003337
FooDB IDFDB023147
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID33951
BioCyc IDNot Available
METLIN ID6893
PDB IDNot Available
Wikipedia LinkGlutathione disulfide
Chemspider ID950
ChEBI ID17858
PubChem Compound ID975
Kegg Compound IDC00127
YMDB IDYMDB00057
ECMDB IDECMDB21221
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Saito, 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.
2. Slivka A, Spina MB, Cohen G: Reduced and oxidized glutathione in human and monkey brain. Neurosci Lett. 1987 Feb 10;74(1):112-8.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
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.
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.
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.
12. 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.
13. 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.
14. 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.
15. Srivastava SK, Beutler E: Oxidized glutathione levels in erythrocytes of glucose-6-phosphate-dehydrogenase-deficient subjects. Lancet. 1968 Jul 6;2(7558):23-4.
16. 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.
17. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.