glutathione

Also known as (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid, glutathione-SH, glutathione reduced, gamma-L-glutamyl-L-cysteinylglycine, L-glutamyl-L-cysteinylglycine, L-gamma-glutamyl-L-cysteinyl-glycine, gamma-glutamylcysteinylglycine, L-glutathione

thumb|Glutathione (GSH) powder

OverviewAI-generated

Glutathione is a compound with the chemical formula C₁₀H₁₇N₃O₆S. It was discovered in 1921. The substance has a mass of 307.084 and a weight of 307.33. Its IUPAC name is (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid.

Chemical properties include an xlogp of -4.5 and a topological polar surface area of 160. The molecule features six hydrogen bond donors and eight hydrogen bond acceptors, with a charge of 0. It is associated with 204071 PubMed entries and is referenced by 897 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C10H17N3O6S
Molecular weight: 307.33 g/mol
IUPAC name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
SMILES: C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
InChIKey: RWSXRVCMGQZWBV-WDSKDSINSA-N
XLogP: -4.5
Polar surface area: 160 Å²
H-bond donors: 6
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: pancreatic carcinoma, ischemia reperfusion injury, persian gulf syndrome, peripheral neuropathy

via ChEMBL · EBI

Research

204,071 papers

Glutathione: subcellular distribution and membrane transport (1).Biochemistry and cell biology = Biochimie et biologie cellulaire · 2019
Detection of Protein-Protein Interactions Using Glutathione-S-Transferase (GST) Pull-Down Assay Technique.Methods in molecular biology (Clifton, N.J.) · 2023
Glutathione S-transferase π: a potential role in antitumor therapy.Drug design, development and therapy · 2018
Implications of glutathione-S transferase P1 in MAPK signaling as a CRAF chaperone: In memory of Dr. Irving Listowsky.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2022
Glutathione S-aralkyltransferase.The Biochemical journal · 1969

via PubMed

Wikidata facts

Subclass of: thiol
Has part: oxygen
Mass: 307.084
Image: Sample of glutathione.jpg
Has use: medication

Show 8 more facts

Commons category: Glutathione
chemical formula: C₁₀H₁₇N₃O₆S
canonical SMILES: C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
isomeric SMILES: C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
found in taxon: broad bean
subject has role: primary metabolite
discoverer or inventor: Frederick Hopkins
time of discovery or invention: 1921-00-00

Sources (7)

via Wikidata · CC0

~9 min read

Encyclopedic overview

14 sections

Contents

Biosynthesis and occurrence
Occurrence
Biochemical function
Roles
Antioxidant
Regulation
Metabolism
Conjugation
In plants
In degradation of drug delivery systems
Uses
Winemaking
See also
References

{{Chembox | Watchedfields = changed | verifiedrevid = 443838068 | Reference = | ImageFile = Glutathione-skeletal.svg | ImageClass = skin-invert-image | ImageFile2 = Glutathione-from-xtal-3D-balls.png | ImageClass2 = bg-transparent | ImageFile3 = Glutathione-3D-vdW.png | ImageClass3 = bg-transparent | IUPACName = γ-Glutamylcysteinylglycine | SystematicName = (2S)-2-Amino-5-({(2R)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanylpropan-2-yl}amino)-5-oxopentanoic acid | OtherNames = γ-L-Glutamyl-L-cysteinylglycine(2S)-2-Amino-4-({(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl}carbamoyl)butanoic acid |Section1= |Section2= |Section6= |Section7= }} thumb|Glutathione (GSH) powder

Glutathione (GSH, ) is a tripeptide made of the amino acids glutamate, cysteine, and glycine. It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, peroxides, lipid peroxides, and heavy metals.

Excerpted from Wikipedia’s “glutathione” article, available under the CC BY-SA 4.0 licence.