Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:03:05 UTC
Update Date2022-08-31 17:43:38 UTC
Metabolite IDMMDBc0030315
Metabolite Identification
Common NameGlutathione disulfide
DescriptionGlutathione (GSH) is a tripeptide with a gamma peptide linkage between the amine group of cysteine (which is attached by normal peptide linkage to a glycine) and the carboxyl group of the glutamate side-chain. It is an antioxidant, preventing damage to important cellular components caused by reactive oxygen species such as free radicals and peroxides. Glutathione is a cofactor for the enzyme glutathione peroxidase. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate.; Glutathione disulfide (GSSG) is a disulfide derived from two glutathione molecules.
Structure
Synonyms
ValueSource
(2S)-2-Azaniumyl-4-{[(1R)-2-{[(2R)-2-[(4S)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoateHMDB
Glutathione disulfideHMDB
GSSGHMDB
L(-)-Glutathione(oxidized)HMDB
OxiglutationeHMDB
Molecular FormulaC20H32N6O12S2
Average Mass612.631
Monoisotopic Mass612.151961898
IUPAC Name2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
Traditional Nameoxiglutatione
CAS Registry Number27025-41-8
SMILES
NC(CCC(=O)NC(CSSCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)
InChI KeyYPZRWBKMTBYPTK-UHFFFAOYSA-N