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70-18-8 molecular structure
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(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 and InChIs

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

Cite this record

CBID:29 http://www.chembase.cn/molecule-29.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
GSH
5-L-Glutamyl-L-cysteinylglycine
gamma-L-Glutamyl-L-cysteinyl-glycine
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine
Gluthathione
γ-L-Glutamyl-L-cysteinylglycine
(2S)-2-Amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo- 3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
γ-L-Glutamyl-L-cysteinyl-glycine
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
L-Glutathione
L-Glutathione reduced
gamma-L-Glutamyl-L-cysteinylglycine
Glutathione
L-Glutathione, reduced
5-L-谷氨酰-L-半胱氨酰甘氨酸
L-还原型谷胱甘肽
L-谷胱甘肽, reduced
CAS Number
70-18-8
EC Number
200-725-4
MDL Number
MFCD00065939
Beilstein Number
1729812
Merck Index
144475
PubChem SID
46504598
24895261
24895164
160963492
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.9364038  H Acceptors
H Donor LogD (pH = 5.5) -6.550201 
LogD (pH = 7.4) -8.083546  Log P -4.884676 
Molar Refractivity 69.1149 cm3 Polarizability 27.466314 Å3
Polar Surface Area 158.82 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -2.74  LOG S -2.54 
Solubility (Water) 8.79e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Freely soluble in water expand Show data source
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble50 mg/mL expand Show data source
Insoluble in methanol, diethyl ether expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
>183°C (dec.) expand Show data source
192-195 °C (dec.)(lit.) expand Show data source
195°C expand Show data source
ca 193°C dec. expand Show data source
Optical Rotation
[α]20/D -17±1°, c = 2% in H2O expand Show data source
[α]25/D -17.0°, c = 2 in H2O expand Show data source
-17 (c=2 in water) expand Show data source
Hydrophobicity(logP)
-6.4 expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
MC0556000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
expand Show data source
GHS Hazard statements
H303 expand Show data source
GHS Precautionary statements
P312 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97.0% (sum of enantiomers, HPLC) expand Show data source
≥98.0% expand Show data source
97% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
cell culture tested expand Show data source
Ignition Residue
≤0.1% expand Show data source
Impurities
≤0.005% Phosphorus (P) expand Show data source
≤0.1% Insoluble matter expand Show data source
≤1% L-glutathione oxid. (enzymatic) expand Show data source
Cation Traces
Al: ≤0.0005% expand Show data source
Ca: ≤0.0005% expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤0.0005% expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤0.0005% expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤0.005% expand Show data source
K: ≤5 mg/kg expand Show data source
Mg: ≤0.0005% expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤0.005% expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: ≤0.05% expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤0.001% expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤0.0005% expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
sulfate (SO42-): ≤0.05% expand Show data source
Quality Level
PREMIUM expand Show data source
Product Line
BioReagent expand Show data source
BioXtra expand Show data source
Linear Formula
H2NCH(CO2H)CH2CH2CONHCH(CH2SH)CONHCH2CO2H expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich DrugBank DrugBank Wikipedia Wikipedia TRC TRC
Sigma Aldrich - G6013 external link
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 - G6529 external link
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 external link
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 external link
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 - G4251 external link
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
DrugBank - DB00143 external link
Item Information
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
Toronto Research Chemicals - G597951 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
  • • 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
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PATENTS

PATENTS

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