(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid

• ChemBase ID: 29
• Molecular Formular: C10H17N3O6S
• Molecular Mass: 307.32348
• Monoisotopic Mass: 307.08380628
• SMILES: SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O
• Canonical SMILES: SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
• InChIKey: RWSXRVCMGQZWBV-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: glutathione
• Brand Name: Tathion; Neuthion; Isethion; Copren; Ledac
• Synonyms: gamma-L-Glutamyl-L-cysteinylglycine; L-Glutathione, reduced; L-Glutathione; L-γ-Glutamyl-L-cysteinyl-glycine; Agifutol S; Bakezyme RX; Copren; Deltathione; Glutathion; Glutathione-SH; Glutide; Glutinal; Isethion; L-Glutathione; Neuthion; Reduced glutathione; Tathion; Tathione; Triptide; γ-L-Glutamyl-L-cysteinyl-glycine; L-Glutathione reduced; γ-L-Glutamyl-L-cysteinylglycine; (2S)-2-Amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo- 3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid; GSH; 5-L-Glutamyl-L-cysteinylglycine; gamma-L-Glutamyl-L-cysteinyl-glycine; N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine; Gluthathione; Glutathione; L-谷胱甘肽, reduced; 5-L-谷氨酰-L-半胱氨酰甘氨酸; L-还原型谷胱甘肽

Database IDs

• CAS Number: 70-18-8
• EC Number: 200-725-4
• MDL Number: MFCD00065939
• Beilstein Number: 1729812
• Merck Index: 144475
• PubChem SID: 24895164; 160963492; 24895261; 46504598; 24895241
• PubChem CID: 124886
• CHEBI ID: 60836
• ATC CODE: V03AB32
• CHEMBL: 1543
• Chemspider ID: 111188
• DrugBank ID: DB00143
• KEGG ID: C00051
• MeSH Name: Glutathione
• Unique Ingredient Identifier: GAN16C9B8O
• Wikipedia Title: Glutathione

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9364038
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -6.550201
• LogD (pH = 7.4): -8.083546
• Log P: -4.884676
• Molar Refractivity: 69.1149 cm^3
• Polarizability: 27.466314 Å^3
• Polar Surface Area: 158.82 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.74
• LOG S: -2.54
• Solubility (Water): 8.79e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Freely soluble in water; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL; Insoluble in methanol, diethyl ether; Water
• Apperance: powder; White Solid
• Melting Point: >183°C (dec.); 192-195 °C (dec.)(lit.); 195°C; ca 193°C dec.
• Optical Rotation: [α]20/D -17±1°, c = 2% in H2O; [α]25/D -17.0°, c = 2 in H2O; -17 (c=2 in water)
• Hydrophobicity(logP): -6.4

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: MC0556000
• German water hazard class: 2
• TSCA Listed: 是
• GHS Hazard statements: H303
• GHS Precautionary statements: P312
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, HPLC); ≥98.0%; 97%; 98%
• Suitability: cell culture tested
• Ignition Residue: ≤0.1%
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; ≤1% L-glutathione oxid. (enzymatic)
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤5 mg/kg; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.005%; Na: ≤50 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤0.05%
• Quality Level: PREMIUM
• Product Line: BioReagent; BioXtra
• Linear Formula: H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
• Classification: Genuine Natural Compounds

DETAILS

DrugBank - DB00143

• Drug Groups: approved; nutraceutical
• Description: A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Toxicity: ORL-MUS LD₅₀ 5000 mg/kg, IPR-MUS LD₅₀ 4020 mg/kg, SCU-MUS LD₅₀ 5000 mg/kg, IVN-RBT LD₅₀ > 2000 mg/kg, IMS-MUS LD₅₀ 4000 mg/kg
• Affected Organisms: Humans and other mammals
• Absorption: Research suggests that glutathione is not orally bioactive, and that very little of oral glutathione tablets or capsules is actually absorbed by the body.
• References: Struzynska L, Chalimoniuk M, Sulkowski G: The role of astroglia in Pb-exposed adult rat brain with respect to glutamate toxicity. Toxicology. 2005 Sep 1;212(2-3):185-94. [Pubmed] ; Witschi A, Reddy S, Stofer B, Lauterburg BH: The systemic availability of oral glutathione. Eur J Clin Pharmacol. 1992;43(6):667-9. [Pubmed] ; Yim CY, Hibbs JB Jr, McGregor JR, Galinsky RE, Samlowski WE: Use of N-acetyl cysteine to increase intracellular glutathione during the induction of antitumor responses by IL-2. J Immunol. 1994 Jun 15;152(12):5796-805. [Pubmed] ; Drevet JR: The antioxidant glutathione peroxidase family and spermatozoa: a complex story. Mol Cell Endocrinol. 2006 May 16;250(1-2):70-9. Epub 2006 Jan 19. [Pubmed] ; Wu G, Fang YZ, Yang S, Lupton JR, Turner ND: Glutathione metabolism and its implications for health. J Nutr. 2004 Mar;134(3):489-92. [Pubmed]
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - G6013

Amino Acid Sequence
γ-Glu-Cys-Gly
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Sigma Aldrich - G4705

Amino Acid Sequence
γ-Glu-Cys-Gly
Application
Biological antioxidant1 that has been used with antitumor agents to enhance activity2 or to reduce side effects.3
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Sigma Aldrich - 49750

Amino Acid Sequence
γ-Glu-Cys-Gly
Application
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Sigma Aldrich - G6529

Amino Acid Sequence
γ-Glu-Cys-Gly
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.

Sigma Aldrich - G4251

Amino Acid Sequence
γ-Glu-Cys-Gly
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
May be used at 5-10 mM to elute glutathione S-transferase (GST) from glutathione agarose.
Biochem/physiol Actions
Endogenous antioxidant that plays a major role in reducing reactive oxygen species formed during cellular metabolism and the respiratory burst. Glutathione-S-transferase catalyzes the formation of glutathione thioethers with xenobiotics, leukotrienes, and other molecules that have an electrophilic center. Glutathione also forms disulfide bonds with cysteine residues in proteins. Via these mechanisms, it can have the paradoxical effect of reducing the efficacy of anti-cancer agents.
Packaging
1, 5, 10, 25, 50, 100, 250, 500 g in poly bottle
300 mg in poly bottle
10 mg in autosmp vl

Toronto Research Chemicals - G597951

Glutathione may decrease the concentrations of inflammatory cytokines (IL-6, IL-18), neutrophils in lung tissue and increase the level of serum Ca2+ and be useful for the treatment of ANP. Glutathione production is regulated via distinct pathways in stre

REFERENCES

• Drevet JR: The antioxidant glutathione peroxidase family and spermatozoa: a complex story. Mol Cell Endocrinol. 2006 May 16;250(1-2):70-9. Epub 2006 Jan 19. Pubmed
• Wu G, Fang YZ, Yang S, Lupton JR, Turner ND: Glutathione metabolism and its implications for health. J Nutr. 2004 Mar;134(3):489-92. Pubmed
• Witschi A, Reddy S, Stofer B, Lauterburg BH: The systemic availability of oral glutathione. Eur J Clin Pharmacol. 1992;43(6):667-9. Pubmed
• Yim CY, Hibbs JB Jr, McGregor JR, Galinsky RE, Samlowski WE: Use of N-acetyl cysteine to increase intracellular glutathione during the induction of antitumor responses by IL-2. J Immunol. 1994 Jun 15;152(12):5796-805. Pubmed
• Struzynska L, Chalimoniuk M, Sulkowski G: The role of astroglia in Pb-exposed adult rat brain with respect to glutamate toxicity. Toxicology. 2005 Sep 1;212(2-3):185-94. Pubmed
• Misko, T., et al.: J. Biol. chem., 273, 15646 (1998)
• Nakamura, K., et al.: J. Biol. Chem., 276, 34402 (1998)
• Burdo, J., et al.: Brain Res. 1189, 12 (2008).