Showing Metabocard for glutathione disulfide (BASm0003352)

Common NameGlutathione disulfide
DescriptionOxidized glutathione, also known as glutathione disulfide or GSSG, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by the formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. In humans, oxidized glutathione is involved in the metabolic disorder called leukotriene C4 synthesis deficiency pathway. Outside of the human body, oxidized glutathione has been detected, but not quantified in several different foods, such as leeks, star anises, mamey sapotes, climbing beans, and common persimmons. Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. Glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. 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 I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione into S-D-lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-lactoyl-glutathione into glutathione and D-lactate.
Structure
Molecular FormulaC20H32N6O12S2
Average Mass612.63100
Monoisotopic Mass612.15196
IUPAC Name2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid
Traditional Name2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-(carboxymethylcarbamoyl)ethyl]disulfanyl}-1-(carboxymethylcarbamoyl)ethyl)carbamoyl]butanoic acid
CAS Registry Number27025-41-8
SMILES[NH3+][C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H]([NH3+])C(=O)[O-])C(=O)NCC(=O)[O-])C(=O)NCC(=O)[O-])C(=O)[O-]
InChI IdentifierInChI=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)/t9-,10-,11-,12-/m0/s1
InChI KeyYPZRWBKMTBYPTK-BJDJZHNGSA-N
CHEBI IDCHEBI:58297
HMDB IDHMDB0003337
Pathways
NameSMPDB/PathBank
Glutathione metabolism
Glutamate Metabolism
Arachidonic Acid Metabolism
Piroxicam Action Pathway
Acetylsalicylic Acid Action Pathway
Etodolac Action Pathway
Ketoprofen Action Pathway
Ibuprofen Action Pathway
Rofecoxib Action Pathway
Diclofenac Action Pathway
Sulindac Action Pathway
Celecoxib Action Pathway
Ketorolac Action Pathway
Suprofen Action Pathway
Bromfenac Action Pathway
Indomethacin Action Pathway
Meloxicam Action Pathway
Mefenamic Acid Action Pathway
Oxaprozin Action Pathway
Nabumetone Action Pathway
Valdecoxib Action Pathway
Naproxen Action Pathway
2-Hydroxyglutric Aciduria (D And L Form)
5-Oxoprolinuria
Gamma-Glutamyltransferase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Diflunisal Action Pathway
Glutathione Synthetase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Leukotriene C4 Synthesis Deficiency
Homocarnosinosis
5-oxoprolinase deficiency
Gamma-glutamyl-transpeptidase deficiency
Succinic semialdehyde dehydrogenase deficiency
Antipyrine Action Pathway
Antrafenine Action Pathway
Carprofen Action Pathway
Etoricoxib Action Pathway
Fenoprofen Action Pathway
Flurbiprofen Action Pathway
Magnesium salicylate Action Pathway
Lumiracoxib Action Pathway
Lornoxicam Action Pathway
Phenylbutazone Action Pathway
Nepafenac Action Pathway
Trisalicylate-choline Action Pathway
Tolmetin Action Pathway
Tiaprofenic Acid Action Pathway
Tenoxicam Action Pathway
Salsalate Action Pathway
Salicylate-sodium Action Pathway
Salicylic Acid Action Pathway
Acetaminophen Action Pathway
StateSolid
Water Solubility4.06e-01 g/l
logP-3.60
logS-3.18
pKa (Strongest Acidic)1.44
pKa (Strongest Basic)9.61
Hydrogen Acceptor Count14
Hydrogen Donor Count10
Polar Surface Area317.64 Ų
Rotatable Bond Count21
Physiological Charge-2
Formal Charge0
Refractivity136.65 m³·mol⁻¹
Polarizability58.41

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