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Record Information
Version1.0
Created at2020-04-17 18:38:34 UTC
Updated at2020-12-07 19:10:59 UTC
CannabisDB IDCDB004805
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Glutathione is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
Chemical FormulaC10H17N3O6S
Average Molecular Weight307.32
Monoisotopic Molecular Weight307.0838
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional Nameglutathione
CAS Registry Number70-18-8
SMILES
N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
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
InChI KeyRWSXRVCMGQZWBV-WDSKDSINSA-N
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point195 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility292.5 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-4.9ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area158.82 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity69.11 m³·mol⁻¹ChemAxon
Polarizability29.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Canalicular multispecific organic anion transporter 1ABCC210q24Q92887 details
Multidrug resistance-associated protein 1ABCC116p13.1P33527 details
Canalicular multispecific organic anion transporter 2ABCC317q22O15438 details
Multidrug resistance-associated protein 4ABCC413q32O15439 details
Multidrug resistance-associated protein 5ABCC53q27O15440 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
Hydroxyacylglutathione hydrolase, mitochondrialHAGH16p13.3Q16775 details
Hydroxyacylglutathione hydrolase-like proteinHAGHLQ6PII5 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
Glutathione peroxidase 3GPX35q23P22352 details
Concentrations Data
Not Available
HMDB IDHMDB0000125
DrugBank IDDB00143
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001498
KNApSAcK IDC00001518
Chemspider ID111188
KEGG Compound IDC00051
BioCyc IDGLUTATHIONE
BiGG ID33669
Wikipedia LinkGlutathione
METLIN ID44
PubChem Compound124886
PDB IDNot Available
ChEBI ID16856
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 60 proteins in total.

Enzymes

General function:
Involved in prostaglandin-E synthase activity
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
O14684
Molecular weight:
17102.135
General function:
Involved in oxidoreductase activity
Specific function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular weight:
56256.565
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
General function:
Involved in lactoylglutathione lyase activity
Specific function:
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B.
Gene Name:
GLO1
Uniprot ID:
Q04760
Molecular weight:
20777.515
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GSS
Uniprot ID:
P48637
Molecular weight:
52384.325
General function:
Involved in enzyme activator activity
Specific function:
Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:
LTC4S
Uniprot ID:
Q16873
Molecular weight:
16566.465
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular weight:
25744.395

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
May be an organic anion pump relevant to cellular detoxification
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular weight:
149525.3
General function:
Involved in ATP binding
Specific function:
Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:
ABCC5
Uniprot ID:
O15440
Molecular weight:
160658.8

Only showing the first 10 proteins. There are 60 proteins in total.