Basic information
- CAS
27025-41-8- Standard SMILES
N[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- InChIKey
YPZRWBKMTBYPTK-BJDJZHNGSA-N- Molecular formula
- C20H32N6O12S2
- Average molar mass
- 612.6 g/mol
- Monoisotopic mass
- 612.15196246
Overview
Glutathione disulfide is a glutathione derivative and an organic disulfide. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a conjugate acid of a glutathione disulfide(2-).
Names & identifiers
- Preferred name
- Glutathione Disulfide
- IUPAC
- (2S)-2-amino-5-[[(2R)-3-[[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
- English name
- L-Glutathione
- Molecular formula
- C20H32N6O12S2
- Molecular weight
- 612.63
Names & synonyms
glutathione disulfideGSSGGlutathione disulphideOxigluthioneGlutathone disulfideOxiglutationaOxiglutationumBis(gamma-glutamyl-L-cysteinylglycine) disulfideULW86O013HDisulfide, GlutathioneRefChem:570552-amino-4-((2-((2-(4-amino-4-carboxybutanamido)-2-((carboxymethyl)carbamoyl)ethyl)disulfanyl)-1-((carboxymethyl)carbamoyl)ethyl)carbamoyl)butanoic acid
Show more names
L-GLUTATHIONE OXIDIZEDL-GLUTATHIONE OXIDISEDoxidizedglutathioneoxidised glutathioneGSSCNOV-002Glutathiol
oxiglutatione27025-41-8Glutathione-ssgOxiglutatione [INN]Bi(glutathion-S-yl)Oxiglutationum [INN-Latin]Oxiglutationa [INN-Spanish]CCRIS 780
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -9.1
- Topological polar surface area
- 368 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 21
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 879
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical Description
Solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
227 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
224.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 178 °C · 178 °C (dec.)(lit.)
- alpha
- -99 · -99 º (c=4, water)
- Density
- 1.3688 · 1.3688 (rough estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 75% (6 of 8) of all reports.
Warning
H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationGlycine, L-.gamma.-glutamyl-L-cysteinyl-, bimol. (2â2')-disulfide: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (25%)
Safety data
- wgk
- 2
- rtecs
- MC0556500
- hs_code
- 29309090
- Toxicity
- mouse,LD50,intravenous,> 2gm/kg (2000mg/kg),Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 6793, 1989.
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25-36/37/39-27-37/39
Chemistry & industry
Pharmacology
Tissue LocationsBrain
Cellular LocationsExtracellular
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)
Uses & manufacturing
UsesA GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. [ChemIDplus]
Applications
DescriptionL-Glutathione oxidized(GSSG) is produced by the oxidation of glutathione. Detoxification of reactive oxygen species is accompanied by production of it. It can be used for the research of sickle cells and erythrocytes. The ratio of glutathione (GSH) to oxidised glutathione (GSSG) is a key indicator of cellular oxidative stress. It can be used in the clinical diagnosis and treatment of leukaemia by detecting the level of cellular GSH/GSSG in acute myeloid leukaemia (AML), which is characterised by oxidative stress leading to abnormally low levels of oxidised glutathione, with real-time, dynamic and highly sensitive characteristics[1].
UsesL-Glutathione is used as a Acts as hydrogen acceptor in enzymatic determination of NADP and NADPH, it is used to reduced back to glutathione (GSH) via the NADPH-dependent enzyme glutathione reductase. The ratio of GSH to GSSG is often used to gauge the level of oxidative stress in cells, with higher concentrations of GSSG implying more oxidative stress, L-Glutathione formation is used to study the polymorphism in glutathione conjugation ac tivity of human erythrocytes towards ethylene dibromide.
Upstream & downstream products
Downstream products
Related reactions
3 records
Compound notes
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