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

• ChemBase编号: 29
• 分子式: C10H17N3O6S
• 平均质量: 307.32348
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
• IUPAC传统名: glutathione
• 商标名: Tathion; Neuthion; Isethion; Copren; Ledac
• 别名: 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; 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

登记号

• CAS号: 70-18-8
• EC号: 200-725-4
• MDL号: MFCD00065939
• Beilstein号: 1729812
• 默克索引号: 144475
• PubChem SID: 160963492; 24895261; 24895164; 46504598; 24895241
• PubChem CID: 124886
• CHEBI ID: 60836
• ATC码: V03AB32
• CHEMBL: 1543
• Chemspider ID: 111188
• DrugBank ID: DB00143
• KEGG ID: C00051
• 医学主题词(MeSH): Glutathione
• 美国药典/FDA物质标识码: GAN16C9B8O
• 维基百科标题: Glutathione

理论计算性质

JChem

• Acid pKa: 1.9364038
• 质子受体: 7
• 质子供体: 6
• LogD (pH = 5.5): -6.550201
• LogD (pH = 7.4): -8.083546
• Log P: -4.884676
• 摩尔折射率: 69.1149 cm^3
• 极化性: 27.466314 Å^3
• 极化表面积: 158.82 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -2.74
• LOG S: -2.54
• 溶解度: 8.79e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Freely soluble in water; H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL; Insoluble in methanol, diethyl ether; Water
• 外观: powder; White Solid
• 熔点: >183°C (dec.); 192-195 °C (dec.)(lit.); 195°C; ca 193°C dec.
• 比旋光度: [α]20/D -17±1°, c = 2% in H2O; [α]25/D -17.0°, c = 2 in H2O; -17 (c=2 in water)
• 疏水性(logP): -6.4

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: MC0556000
• 德国WGK号: 2
• TSCA收录: 是
• GHS危险声明: H303
• GHS警示性声明: P312
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (sum of enantiomers, HPLC); ≥98.0%; 97%; 98%
• 适用性: cell culture tested
• 燃烧残渣: ≤0.1%
• 杂质: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; ≤1% L-glutathione oxid. (enzymatic)
• 痕量阳离子: 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
• 痕量阴离子: sulfate (SO42-): ≤0.05%
• 产品质量级别: PREMIUM
• 产品线: BioReagent; BioXtra
• 线性分子式: H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H
• 分类: Genuine Natural Compounds

详细说明

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
可用 5-10mM 浓度的产品从谷胱甘肽琼脂糖中洗提谷胱甘肽 S-转移酶 (GST)。
Biochem/physiol Actions
在细胞代谢和突发性呼吸期间形成的活性氧还原中发挥重要作用的内源性抗氧化剂。谷胱甘肽-S-转移酶催化谷胱甘肽硫醚与异生物、白三烯和其他具有亲电中心的分子的形成。谷胱甘肽还与蛋白质中半胱氨酸残基形成二硫键。通过这些机制，它可具有降低抗癌剂效用的奇异效果。

Sigma Aldrich - G4705

Amino Acid Sequence
γ-Glu-Cys-Gly
Application
可用 5-10mM 浓度的产品从谷胱甘肽琼脂糖中洗提谷胱甘肽 S-转移酶 (GST)。
生物抗氧化剂1，已与抗肿瘤剂共同用于提高活性2或者降低副作用。3
Biochem/physiol Actions
在细胞代谢和突发性呼吸期间形成的活性氧还原中发挥重要作用的内源性抗氧化剂。谷胱甘肽-S-转移酶催化谷胱甘肽硫醚与异生物、白三烯和其他具有亲电中心的分子的形成。谷胱甘肽还与蛋白质中半胱氨酸残基形成二硫键。通过这些机制，它可具有降低抗癌剂效用的奇异效果。

Sigma Aldrich - 49750

Amino Acid Sequence
γ-Glu-Cys-Gly
Application
可用 5-10mM 浓度的产品从谷胱甘肽琼脂糖中洗提谷胱甘肽 S-转移酶 (GST)。
Biochem/physiol Actions
在细胞代谢和突发性呼吸期间形成的活性氧还原中发挥重要作用的内源性抗氧化剂。谷胱甘肽-S-转移酶催化谷胱甘肽硫醚与异生物、白三烯和其他具有亲电中心的分子的形成。谷胱甘肽还与蛋白质中半胱氨酸残基形成二硫键。通过这些机制，它可具有降低抗癌剂效用的奇异效果。

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
可用 5-10mM 浓度的产品从谷胱甘肽琼脂糖中洗提谷胱甘肽 S-转移酶 (GST)。
Biochem/physiol Actions
在细胞代谢和突发性呼吸期间形成的活性氧还原中发挥重要作用的内源性抗氧化剂。谷胱甘肽-S-转移酶催化谷胱甘肽硫醚与异生物、白三烯和其他具有亲电中心的分子的形成。谷胱甘肽还与蛋白质中半胱氨酸残基形成二硫键。通过这些机制，它可具有降低抗癌剂效用的奇异效果。

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
可用 5-10mM 浓度的产品从谷胱甘肽琼脂糖中洗提谷胱甘肽 S-转移酶 (GST)。
Biochem/physiol Actions
在细胞代谢和突发性呼吸期间形成的活性氧还原中发挥重要作用的内源性抗氧化剂。谷胱甘肽-S-转移酶催化谷胱甘肽硫醚与异生物、白三烯和其他具有亲电中心的分子的形成。谷胱甘肽还与蛋白质中半胱氨酸残基形成二硫键。通过这些机制，它可具有降低抗癌剂效用的奇异效果。
包装
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

参考文献

• 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).