Record Information
Version1.0
Creation date2015-10-09 22:28:07 UTC
Update date2017-01-19 02:36:12 UTC
FoodComEx IDPC000085
FoodDB RecordFDB001498
Chemical Information
NameGlutathione
DescriptionGlutathione, also known as GSH or agifutol S, 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 formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Glutathione is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Glutathione is a very strong basic compound (based on its pKa). A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine. Glutathione exists in all living species, ranging from bacteria to humans. Within humans, glutathione participates in a number of enzymatic reactions. In particular, leukotriene A4 and glutathione can be converted into leukotriene C4 through its interaction with the enzyme leukotriene C4 synthase. In addition, 15(S)-hpete and glutathione can be converted into 15(S)-hete and oxidized glutathione through its interaction with the enzyme glutathione peroxidase 1. In humans, glutathione is involved in mefenamic acid action pathway. Outside of the human body, Glutathione is found, on average, in the highest concentration within a few different foods, such as purslanes, spinachs, and corns. Glutathione has also been detected, but not quantified in, several different foods, such as yautia, coconuts, common salsifies, pigeon pea, and ohelo berries. This could make glutathione a potential biomarker for the consumption of these foods. Glutathione is a potentially toxic compound.
CAS Number70-18-8
Structure
Thumb
Synonyms
SynonymSource
5-L-Glutamyl-L-cysteinylglycinebiospider
Agifutol SHMDB
Bakezyme rxHMDB
CoprenHMDB
DeltathioneHMDB
g-L-Glutamyl-L-cysteinyl-glycineGenerator
gamma-Glutamylcysteinylglycinebiospider
gamma-L-Glutamyl-L-cysteinyl-glycinebiospider
gamma-L-Glutamyl-L-cysteinylglycineHMDB
GlutathionHMDB
Glutathionebiospider
Glutathione (reduced)biospider
Glutathione redHMDB
Glutathione reducedHMDB
Glutathione-SHbiospider
Glutathione, reduced formbiospider
GlutatiolHMDB
GlutationeHMDB
GlutideHMDB
GlutinalHMDB
GSHmanual
IsethionHMDB
L-g-Glutamyl-L-cysteinyl-glycinebiospider
L-gamma-Glutamyl-L-cysteinyl-glycinebiospider
L-gamma-Glutamyl-L-cysteinylglycineHMDB
L-Glutamyl-L-cysteinylglycineHMDB
L-Glutathionedb_source
L-Glutathione reduceHMDB
L-Glutathione reducedbiospider
LedacHMDB
N-(N-g-L-Glutamyl-L-cysteinyl)glycineGenerator
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycinebiospider
N-(N-L-gamma-Glutamyl-L-cysteinyl)glycinebiospider
N-(N-γ-L-glutamyl-L-cysteinyl)glycineGenerator
NeuthionHMDB
Red. glutathioneHMDB
Reduced glutathionebiospider
TathionHMDB
TathioneHMDB
TriptideHMDB
γ-L-glutamyl-L-cysteinyl-glycineGenerator
Chemical FormulaNot Available
IUPAC nameNot Available
InChI IdentifierInChI=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
InChI KeyRWSXRVCMGQZWBV-WDSKDSINSA-N
Isomeric SMILESN[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
Average Molecular Weight307.323
Monoisotopic Molecular Weight307.083805981
Chemical Taxonomy
Description 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 formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid or derivatives
  • Amino acid
  • Alkylthiol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting Point195 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 4 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci J10806
AKSci J91462
AKSci X7257
AKSci HMDB0000125
Cayman Chemical 10007461
Glentham GE1520
MetaSci HMDB0000125
Toronto Research Chemicals G597951