Glutathione

Glutathione
Names


IUPAC name (2S)-2-Amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
Other names γ-L-Glutamyl-L-cysteinylglycine (2S)-2-Amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
Identifiers
CAS Number	70-18-8^Y
3D model (Jmol)	Interactive image
Abbreviations	GSH
ChEBI	CHEBI:60836^Y
ChEMBL	ChEMBL1543^Y
ChemSpider	111188^Y
DrugBank	DB00143^Y
ECHA InfoCard	100.000.660
IUPHAR/BPS	6737
KEGG	C00051^Y
MeSH	Glutathione
PubChem	124886
UNII	GAN16C9B8O^Y
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^Y Key: RWSXRVCMGQZWBV-WDSKDSINSA-N^Y InChI=1/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 Key: RWSXRVCMGQZWBV-WDSKDSINBK
SMILES C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
Properties
Chemical formula	C₁₀H₁₇N₃O₆S
Molar mass	307.32 g·mol⁻¹
Melting point	195 °C (383 °F; 468 K)
Solubility in water	Freely soluble
Solubility in methanol, diethyl ether	Insoluble
Pharmacology
ATC code	V03AB32 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Glutathione (GSH) is an important antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by reactive oxygen species such as free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and the amine group of cysteine, and the carboxyl group of cysteine is attached by normal peptide linkage to a glycine.

Thiol groups are reducing agents, existing at a concentration around 5 mM in animal cells. Glutathione reduces disulfide bonds formed within cytoplasmic proteins to cysteines by serving as an electron donor. In the process, glutathione is converted to its oxidized form, glutathione disulfide (GSSG), also called L-(–)-glutathione.

Once oxidized, glutathione can be reduced back by glutathione reductase, using NADPH as an electron donor. The ratio of reduced glutathione to oxidized glutathione within cells is often used as a measure of cellular oxidative stress.

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Wikipedia