CAS 70-18-8|CAS 98726-08-0|(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid|glutathione|(2<i>S</i>)-2-Amino-5-[[(2<i>R</i>)-1-(carboxymethylamino)-1-oxo- 3-...

(2S)-2-Amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo- 3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acidγ-L-Glutamyl-L-cysteinylglycineGlutathioneγ-L-Glutamyl-L-cysteinyl-glycineL-还原型谷胱甘肽GSHL-Glutathione reduced5-L-谷氨酰-L-半胱氨酰甘氨酸5-L-Glutamyl-L-cysteinylglycinegamma-L-Glutamyl-L-cysteinyl-glycineGluthathioneN-(N-gamma-L-Glutamyl-L-cysteinyl)glycineL-GlutathioneCoprenBakezyme RXDeltathioneGlutathionGlutideAgifutol STathioneGlutinalNeuthionL-γ-Glutamyl-L-cysteinyl-glycineGlutathione-SHTathionReduced glutathioneTriptideL-GlutathioneIsethiongamma-L-Glutamyl-L-cysteinylglycineL-Glutathione, reducedL-谷胱甘肽, reducedglutathionegamma-L-Glutamyl-L-cysteinyl-glycineGSHReduced glutathione5-L-Glutamyl-L-cysteinylglycineN-(N-gamma-L-Glutamyl-L-cysteinyl)glycineGlutathione-SHGlutathionephytochelatinsphytochelatin

IUPAC Traditional name

glutathione

IUPAC name

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

Brand Name

IsethionNeuthionTathionLedacCopren

API Name

Glutathione

Names and Identifiers

Registration numbers

MDL Number

Beilstein Number

EC Number

CAS Number

PubChem SID

2489524124895261160963492465045982489516411533291104222367

MeSH Name

Chemspider ID

KEGG ID

PubChem CID

DrugBank ID

ATC CODE

CHEBI ID

60836CHEBI:12402CHEBI:5437CHEBI:24334CHEBI:43049CHEBI:42873CHEBI:14327CHEBI:16856CHEBI:60836

CHEMBL

1543CHEMBL1543

Unique Ingredient Identifier

GAN16C9B8O

Merck Index

144475

Wikipedia Title

GlutathionePhytochelatin

PubMed Citation Links

1958082316391576164044761678023782072091662173847456544200890149884351611241616877380136295617439666166503981631693110577998

BKMS React Database

3073530912294892282919169154427593537082294884494256

BRENDA Database

4.1.1.325.1.1.15.3.4.13.5.3.91.13.11.272.3.1.652.7.1.562.7.1.825.3.99.43.1.4.172.1.1.22.4.1.12.7.1.943.4.22.246.2.1.1

KNApSAcK Database

C00001518

BRENDA Ligand Database

593154427910479524693826537081061959169951673091449344312323394256

Protein Data Bank

1grx1hnl1qgj2imi4al05f066f662brq3zmk1m0u5aiv2pmt2wb93khq3m3m4kf9

MetaboLights Database

MTBLS530MTBLS1044MTBLS2870MTBLS4579MTBLS405MTBLS8MTBLS868MTBLS1040MTBLS1801MTBLS4495MTBLS2274MTBLS158MTBLS3038MTBLS3657MTBLS419

Reaxys Registry

1729812

MetaCyc Database

GLUTATHIONE

CompTox Database

DTXSID6023101

SABIO-RK Database

103291617061118721349833101187592695771078013721972118701210210291

UniProt Database

P14141Q3KJQ5P0C291Q9I4K6Q0I5A5Q61846O23264P48638Q5RBL6B7UHB1A9N563Q601Q3Q5QLR2C0Q0D3Q8XA20

Patent number

EP1961418EP1070710EP1829551WO2007103435EP1790238US2007191281US2008274888US2005130904WO2007109633EP1712220WO2007135242US2003207344EP1917969WO2007116428

Reactom Database

R-HSA-9035966R-HSA-1247915R-HSA-3323079R-HSA-3301943R-HSA-6799695R-HSA-3341397R-HSA-1500817R-HSA-1655879R-HSA-8943279R-HSA-5693724R-HSA-2161660R-HSA-9011595R-HSA-176059R-HSA-3323013

BioModels Database

BIOMD0000000450BIOMD0000000575BIOMD0000000674BIOMD0000000547BIOMD0000000609BIOMD0000000589BIOMD0000000353BIOMD0000000268BIOMD0000000070BIOMD0000000474BIOMD0000000624BIOMD0000001061

IntAct Database

EBI-21945658EBI-27072957EBI-21986471EBI-21945552EBI-27072995EBI-11301756EBI-11301741EBI-21945598EBI-27072856EBI-21981648

PDBeChem Database

GSH

EnzymePortal Database

P95806B0LDU5P83654P31663Q12068

FooDB Database

FDB001498

Drug Central Database

KEGG DRUG Database

SureChEMBL Database

HMDB Database

GeneOntology Database

GO:0071993GO:0046937GO:0046938GO:0071995GO:0044604GO:0071994

Registration numbers

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Glutathione

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.

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.

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.

TRC

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

ChEBI

CHEBI:16856

A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine.

CHEBI:60836

A family of peptides related to glutathione and composed of (gamma-Glu-Cys)n-Gly where n is in the range 2-11.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Witschi A, Reddy S, Stofer B, Lauterburg BH: The systemic availability of oral glutathione. Eur J Clin Pharmacol. 1992;43(6):667-9. 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

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:29