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
ValueSource
5-L-Glutamyl-L-cysteinylglycineChEBI
gamma-L-Glutamyl-L-cysteinyl-glycineChEBI
Glutathione-SHChEBI
GSHChEBI
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycineChEBI
Reduced glutathioneChEBI
Poly(gamma-glutamylcysteine)glycineKegg
(gamma-Glutamylcysteine)N-glycineKegg
TathionKegg
g-L-Glutamyl-L-cysteinyl-glycineGenerator
Γ-L-glutamyl-L-cysteinyl-glycineGenerator
N-(N-g-L-Glutamyl-L-cysteinyl)glycineGenerator
N-(N-Γ-L-glutamyl-L-cysteinyl)glycineGenerator
Poly(g-glutamylcysteine)glycineGenerator
Poly(γ-glutamylcysteine)glycineGenerator
(g-Glutamylcysteine)N-glycineGenerator
(Γ-glutamylcysteine)N-glycineGenerator
Agifutol SHMDB
Bakezyme RXHMDB
CoprenHMDB
DeltathioneHMDB
gamma-GlutamylcysteinylglycineHMDB
gamma-L-Glutamyl-L-cysteinylglycineHMDB
GlutathionHMDB
Glutathione redHMDB
Glutathione reducedHMDB
GlutatiolHMDB
GlutationeHMDB
GlutideHMDB
GlutinalHMDB
IsethionHMDB
L-g-Glutamyl-L-cysteinyl-glycineHMDB
L-gamma-Glutamyl-L-cysteinyl-glycineHMDB
L-gamma-Glutamyl-L-cysteinylglycineHMDB
L-Glutamyl-L-cysteinylglycineHMDB
L-GlutathioneHMDB
L-Glutathione reduceHMDB
LedacHMDB
NeuthionHMDB
Red. glutathioneHMDB
TathioneHMDB
TriptideHMDB
Glutathione, reducedHMDB
gamma L Glu L cys glyHMDB
gamma-L-Glu-L-cys-glyHMDB
gamma L Glutamyl L cysteinylglycineHMDB
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
TypeDescriptionSplash KeyView
GC-MSGlutathione, x TMS, GC-MS Spectrumsplash10-0a4i-0900000000-5841845f736f9a667622Spectrum
GC-MSGlutathione, x TMS, GC-MS Spectrumsplash10-0a4i-0900000000-bdecde153761cb67852eSpectrum
GC-MSGlutathione, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-5841845f736f9a667622Spectrum
GC-MSGlutathione, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-bdecde153761cb67852eSpectrum
GC-MSGlutathione, non-derivatized, GC-MS Spectrumsplash10-0a4i-1910000000-52bc43dd913b68d74f84Spectrum
GC-MSGlutathione, non-derivatized, GC-MS Spectrumsplash10-08fs-3960000000-63ce34def2ae94b95515Spectrum
GC-MSGlutathione, non-derivatized, GC-MS Spectrumsplash10-0pb9-0921000000-88168b0a9f5fc5fead3fSpectrum
Predicted GC-MSGlutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7890000000-5853006f66d946dd3d2eSpectrum
Predicted GC-MSGlutathione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-9112300000-e82cf72540c283d8e323Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-3795000000-d019cd7dcbad1f8a9e78Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9400000000-a83bf6292d41988256e3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-305a92f8a9ffea58fa0eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009000000-e950bfc5867b391c6960Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0910000000-83f6c079d1112e74ecf4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-003r-0910000000-5b243cf8bd357ab270b1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009000000-29ef335479f56b620d88Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009001000-d1f5986166efa523d024Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-056s-0495300000-dba7be381fd1ef776527Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0920000000-de5b8a5a377324599b39Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-053r-0007920000-7500cef211e48c8ea244Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0119003000-4eb7ed4e2a4cf6a83c66Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0290000000-6893386899c6eed6a1a6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-05g0-0190000000-cacc2de4ab18ed59798bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0009000000-6b4268add43ab66ef015Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-08fr-0015009000-a01bdc13a34d6ce8416fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0290000000-ea94ec8247b4e025adbeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0039210000-e1f721157a9ea89959d6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a59-0039210000-35ce450ea95922abf0e1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0009000000-9b01fba547d1fcde113aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0952000000-4a2a42699cf4aab2c559Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002f-2900000000-bd9ba27b48b1322b7618Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004m-5900000000-cc7184d5bba50e6e49d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-aecd0eb18a10c3ffb7abSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0729-4492000000-78a928563adf9038ba59Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin E synthasePTGES9q34.3O14684 details
Glutathione reductase, mitochondrialGSR8p21.1P00390 details
Peroxiredoxin-6PRDX61q25.1P30041 details
Lactoylglutathione lyaseGLO16p21.3-p21.1Q04760 details
S-formylglutathione hydrolaseESD13q14.1-q14.2P10768 details
Gamma-glutamyltranspeptidase 1GGT122q11.23P19440 details
Gamma-glutamyltransferase 7GGT720q11.22Q9UJ14 details
Glutathione synthetaseGSS20q11.2P48637 details
Leukotriene C4 synthaseLTC4S5q35Q16873 details
Glutathione S-transferase Mu 2GSTM21p13.3P28161 details
Glutathione peroxidase 7GPX71p32Q96SL4 details
Epididymal secretory glutathione peroxidaseGPX56p22.1O75715 details
Glutathione S-transferase Mu 1GSTM11p13.3P09488 details
Hydroxyacylglutathione hydrolase, mitochondrialHAGH16p13.3Q16775 details
Glutathione S-transferase kappa 1GSTK17q34Q9Y2Q3 details
Microsomal glutathione S-transferase 3MGST31q23O14880 details
Glutathione S-transferase Mu 3GSTM31p13.3P21266 details
Glutathione S-transferase A1GSTA16p12.1P08263 details
Maleylacetoacetate isomeraseGSTZ114q24.3O43708 details
Microsomal glutathione S-transferase 1MGST112p12.3-p12.1P10620 details
Glutathione S-transferase Mu 4GSTM41p13.3Q03013 details
Glutathione S-transferase Mu 5GSTM51p13.3P46439 details
Microsomal glutathione S-transferase 2MGST24q28.3Q99735 details
Glutathione S-transferase omega-1GSTO110q25.1P78417 details
Glutathione S-transferase A5GSTA56p12.2Q7RTV2 details
Glutathione S-transferase A2GSTA26p12.1P09210 details
Glutathione peroxidase 6GPX66p22.1P59796 details
Glutathione S-transferase A3GSTA36p12.1Q16772 details
Glutathione S-transferase A4GSTA46p12.1O15217 details
Glutathione peroxidase 1GPX13p21.3P07203 details
Phospholipid hydroperoxide glutathione peroxidase, mitochondrialGPX419p13.3P36969 details
Glutathione peroxidase 3GPX35q23P22352 details
Glutathione S-transferase omega-2GSTO210q25.1Q9H4Y5 details
Glutathione S-transferase theta-1GSTT122q11.23P30711 details
Glutathione peroxidase 2GPX214q24.1P18283 details
Glutathione S-transferase PGSTP111q13P09211 details
Hematopoietic prostaglandin D synthaseHPGDS4q22.3O60760 details
Glutaredoxin-1GLRX5q14P35754 details
Glutaredoxin-2, mitochondrialGLRX21q31.2-q31.3Q9NS18 details
Hydroxyacylglutathione hydrolase-like proteinHAGHLQ6PII5 details
Gamma-glutamyltransferase 6GGT617p13.2Q6P531 details
Thioredoxin domain-containing protein 12TXNDC121p32.3O95881 details
GGT7 proteinGGT720q11.22A0PJJ9 details
Gamma-glutamyltransferase 5GGT522q11.23P36269 details
Glutathione S-transferase theta-2GSTT2P0CG29 details
Gamma-glutamyltranspeptidase 2GGT2P36268 details
Putative gamma-glutamyltranspeptidase 3GGT3PA6NGU5 details
Probable glutathione peroxidase 8GPX85q11.2Q8TED1 details
Glutathione S-transferase theta-2BGSTT2B22q11.23P0CG30 details
Glutathione S-transferase theta-4GSTT4A8MPT4 details
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.