Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2018-01-23 18:49:32 UTC
Primary IDFDB001498
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlutathione
DescriptionGlutathione (GSH) - reduced glutathione - 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. [Wikipedia]. Glutathione is found in many foods, some of which are cashew nut, epazote, ucuhuba, and canada blueberry.
CAS Number70-18-8
Structure
Thumb
Synonyms
SynonymSource
5-L-Glutamyl-L-cysteinylglycineChEBI
gamma-L-Glutamyl-L-cysteinyl-glycineChEBI
Glutathione-SHChEBI
GSHChEBI
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycineChEBI
Reduced glutathioneChEBI
TathionKegg
Poly(gamma-glutamylcysteine)glycineKegg
(gamma-Glutamylcysteine)N-glycineKegg
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
Bakezyme rxHMDB
Glutathionebiospider
Glutathione (reduced)biospider
Glutathione, reduced formbiospider
L-Glutathione reducedbiospider
N-(N-L-gamma-Glutamyl-L-cysteinyl)glycinebiospider
N-(N-γ-L-glutamyl-L-cysteinyl)glycineGenerator
γ-L-glutamyl-L-cysteinyl-glycineGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H17N3O6S
IUPAC name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
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
Classification
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point195 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-0a4i-0900000000-5841845f736f9a667622View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-0a4i-0900000000-bdecde153761cb67852eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-5841845f736f9a667622View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-bdecde153761cb67852eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-1910000000-52bc43dd913b68d74f84View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-08fs-3960000000-63ce34def2ae94b95515View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pb9-0921000000-88168b0a9f5fc5fead3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7890000000-5853006f66d946dd3d2eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0596-9112300000-e82cf72540c283d8e323View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-3795000000-d019cd7dcbad1f8a9e78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9400000000-a83bf6292d41988256e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-305a92f8a9ffea58fa0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009000000-e950bfc5867b391c6960View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0910000000-83f6c079d1112e74ecf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-003r-0910000000-5b243cf8bd357ab270b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009000000-29ef335479f56b620d88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0009001000-d1f5986166efa523d024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-056s-0495300000-dba7be381fd1ef776527View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0920000000-de5b8a5a377324599b39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-053r-0007920000-7500cef211e48c8ea244View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0119003000-4eb7ed4e2a4cf6a83c66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0290000000-6893386899c6eed6a1a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-05g0-0190000000-cacc2de4ab18ed59798bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0009000000-6b4268add43ab66ef015View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-08fr-0015009000-a01bdc13a34d6ce8416fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0290000000-ea94ec8247b4e025adbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0039210000-e1f721157a9ea89959d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a59-0039210000-35ce450ea95922abf0e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0009000000-9b01fba547d1fcde113aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0952000000-4a2a42699cf4aab2c559View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002f-2900000000-bd9ba27b48b1322b7618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004m-5900000000-cc7184d5bba50e6e49d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-aecd0eb18a10c3ffb7abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0729-4492000000-78a928563adf9038ba59View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID111188
ChEMBL IDCHEMBL1543
KEGG Compound IDC02471
Pubchem Compound ID124886
Pubchem Substance IDNot Available
ChEBI ID16856
Phenol-Explorer IDNot Available
DrugBank IDDB00143
HMDB IDHMDB00125
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGLUTATHIONE
BIGG ID33669
KNApSAcK IDC00001518
HET IDGSH
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlutathione
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
anti cytotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatitic62868 Any compound that is able to prevent damage to the liver.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Enzymes
NameGene NameUniProt ID
Glutathione synthetaseGSSP48637
Glutathione S-transferase Mu 3GSTM3P21266
Glutathione S-transferase omega-1GSTO1P78417
Glutathione S-transferase A2GSTA2P09210
Glutathione S-transferase PGSTP1P09211
Glutathione S-transferase Mu 2GSTM2P28161
Glutathione S-transferase Mu 1GSTM1P09488
Glutathione S-transferase kappa 1GSTK1Q9Y2Q3
Microsomal glutathione S-transferase 3MGST3O14880
Glutathione S-transferase A1GSTA1P08263
Microsomal glutathione S-transferase 1MGST1P10620
Glutathione S-transferase Mu 4GSTM4Q03013
Glutathione S-transferase Mu 5GSTM5P46439
Microsomal glutathione S-transferase 2MGST2Q99735
Glutathione S-transferase A5GSTA5Q7RTV2
Glutathione S-transferase A3GSTA3Q16772
Glutathione S-transferase A4GSTA4O15217
Glutathione S-transferase omega-2GSTO2Q9H4Y5
Hematopoietic prostaglandin D synthaseHPGDSO60760
Glutathione peroxidase 7GPX7Q96SL4
Epididymal secretory glutathione peroxidaseGPX5O75715
Glutathione peroxidase 6GPX6P59796
Glutathione peroxidase 1GPX1P07203
Phospholipid hydroperoxide glutathione peroxidase, mitochondrialGPX4P36969
Glutathione peroxidase 3GPX3P22352
Glutathione peroxidase 2GPX2P18283
Prostaglandin E synthasePTGESO14684
Peroxiredoxin-6PRDX6P30041
S-formylglutathione hydrolaseESDP10768
Gamma-glutamyltranspeptidase 1GGT1P19440
Gamma-glutamyltransferase 7GGT7Q9UJ14
Leukotriene C4 synthaseLTC4SQ16873
Maleylacetoacetate isomeraseGSTZ1O43708
Glutaredoxin-1GLRXP35754
Glutaredoxin-2, mitochondrialGLRX2Q9NS18
Gamma-glutamyltransferase 6GGT6Q6P531
Thioredoxin domain-containing protein 12TXNDC12O95881
Gamma-glutamyltransferase 5GGT5P36269
Glutathione S-transferase theta-2GSTT2P0CG29
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.