2.02012-05-31 10:21:27 -06002015-09-13 12:56:06 -0600ECMDB00125M2MDB000048GlutathioneGlutathione (GSH) is a compound synthesized from cysteine. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. Glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione binds with toxic chemicals in order to detoxify them. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in the bacterial cytosol. γ-L-glutamyl-L-cysteinyl-glycine5-L-Glutamyl-L-cysteinylglycineAgifutol SBakezyme RXCoprenDeltathioneg-Glutamylcysteinylglycineg-L-Glutamyl-L-cysteinyl-glycineg-L-Glutamyl-L-cysteinylglycineGamma-GlutamylcysteinylglycineGamma-L-Glutamyl-L-cysteinyl-glycineGamma-L-Glutamyl-L-cysteinylglycineGlutathionGlutathionateGlutathioneGlutathione redGlutathione reducedGlutathione-SHGlutathionic acidGlutatiolGlutationeGlutideGlutinalGSHIsethionL-g-Glutamyl-L-cysteinyl-glycineL-g-Glutamyl-L-cysteinylglycineL-gamma-Glutamyl-L-cysteinyl-glycineL-gamma-Glutamyl-L-cysteinylglycineL-Glutamyl-L-cysteinylglycineL-GlutathioneL-Glutathione reduceL-γ-Glutamyl-L-cysteinyl-glycineL-γ-Glutamyl-L-cysteinylglycineLedacNeuthionRed. glutathioneReduced glutathioneTathionTathioneTriptideγ-Glutamylcysteinylglycineγ-L-Glutamyl-L-cysteinyl-glycineγ-L-Glutamyl-L-cysteinylglycineC10H17N3O6S307.323307.083805981(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acidglutathione70-18-8N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=OInChI=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/s1RWSXRVCMGQZWBV-WDSKDSINSA-NSolidCytosolExtra-organismPeriplasmlogp-2.74logs-2.54solubility8.79e-01 g/lmelting_point195 oClogp-4.9pka_strongest_acidic1.94pka_strongest_basic9.22iupac(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acidaverage_mass307.323mono_mass307.083805981smilesN[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=OformulaC10H17N3O6SinchiInChI=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/s1inchikeyRWSXRVCMGQZWBV-WDSKDSINSA-Npolar_surface_area158.82refractivity69.11polarizability29.11rotatable_bond_count9acceptor_count7donor_count6physiological_charge-1formal_charge0Glutathione metabolismThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW000833ec00480MetabolicCysteine and methionine metabolismec00270Pyruvate metabolismec00620Methane metabolismec00680Metabolism of xenobiotics by cytochrome P450ec00980Drug metabolism - cytochrome P450ec00982Arachidonic acid metabolismDelete Pathway
Arachidonate (arachidonic acid) is a polyunsaturated ω-6 fatty acid with a 20-carbon chain and four cis-double bonds. It is produced at high levels by mosses, some plants, and by some marine bacteria.
Mammals cannot synthesize arachidonate de novo, but most mammals are able to synthesize it from simpler unsaturated fatty acids.
In addition to being involved in cellular signaling as a lipid second messenger, arachidonate is also a key inflammatory intermediate and can also act as a vasodilator.
Like other fatty acids, arachidonate is rarely found in its free form. It is usually found either as arachidonoyl-CoA or incorporated into a lipid.
It is produced from phosphatidylcholine through a phospholipase A1PW000759ec00590MetabolicMicrobial metabolism in diverse environmentsec01120ABC transportersec02010Metabolic pathwayseco01100Selenium metabolismThe selenium metabolism begins with the introduction of selenate and selenite to the cytosol through a sulphate permease system. Once in the cell, selenate can be reduced to selenite through nitrate reductases A and Z. Selenite then interacts with glutathione and 2 hydrogen ions resulting in the release of 2 water molecules, a hydroxide molecule, a glutathione disulfide and a selenodiglutathione. The latter compound then reacts with NADPH+H resulting in the release of a NADP, a glutathione and a glutathioselenol.
Glutathiolselenol can then be oxidize resulting in a a glutathiolselenol ion which can then interact with a water molecule resulting in a release of glutathion and selenium
Glutathiolselenol can also react with NADPH and hydrogen ion resulting in a release of glutathione, NADP, a hydroxide molecule and a hydrogen selenide. This compound can react in a reversible reaction by being oxidized resulting in a hydrogen selenide ion . This compound can then be phosphorylated by interacting with an ATP and releasing a AMP, a phosphate and a selenophosphate.PW001894Metabolicglutathione metabolism IIThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene through a glutathione S-transferase
PW001927Metabolicglutathione metabolism IIIThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW002018Metabolicglutathione biosynthesisGLUTATHIONESYN-PWYglutathione redox reactions IIGLUT-REDOX-PWYmethylglyoxal degradation IPWY-5386formaldehyde oxidation II (glutathione-dependent)PWY-1801Specdb::CMs348Specdb::CMs349Specdb::CMs3305Specdb::CMs30368Specdb::CMs30369Specdb::CMs32175Specdb::CMs32176Specdb::CMs32177Specdb::CMs37307Specdb::CMs155109Specdb::CMs1050923Specdb::CMs1050925Specdb::CMs1050927Specdb::CMs1050929Specdb::CMs1050930Specdb::CMs1050932Specdb::CMs1050934Specdb::CMs1050936Specdb::CMs1050938Specdb::CMs1050940Specdb::CMs1050942Specdb::CMs1050944Specdb::CMs1050946Specdb::CMs1050947Specdb::CMs1050949Specdb::NmrOneD1096Specdb::NmrOneD1155Specdb::NmrOneD142370Specdb::NmrOneD142371Specdb::NmrOneD142372Specdb::NmrOneD142373Specdb::NmrOneD142374Specdb::NmrOneD142375Specdb::NmrOneD142376Specdb::NmrOneD142377Specdb::NmrOneD142378Specdb::NmrOneD142379Specdb::NmrOneD142380Specdb::NmrOneD142381Specdb::NmrOneD142382Specdb::NmrOneD142383Specdb::NmrOneD142384Specdb::NmrOneD142385Specdb::NmrOneD142386Specdb::NmrOneD142387Specdb::NmrOneD142388Specdb::NmrOneD142389Specdb::NmrOneD166513Specdb::MsMs186Specdb::MsMs187Specdb::MsMs188Specdb::MsMs2947Specdb::MsMs2948Specdb::MsMs2949Specdb::MsMs2950Specdb::MsMs2951Specdb::MsMs2952Specdb::MsMs2953Specdb::MsMs2954Specdb::MsMs2955Specdb::MsMs2956Specdb::MsMs2957Specdb::MsMs2958Specdb::MsMs2959Specdb::MsMs2960Specdb::MsMs2961Specdb::MsMs2962Specdb::MsMs2963Specdb::MsMs2964Specdb::MsMs2965Specdb::MsMs2966Specdb::MsMs2967Specdb::MsMs179877Specdb::NmrTwoD1154HMDB00125124886111188C0005116856GLUTATHIONEGTTGlutathioneKeseler, I. 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Curr Drug Targets Immune Endocr Metabol Disord. 2005 Jun;5(2):153-61.16089347Calvo-Marzal P, Chumbimuni-Torres KY, Hoehr NF, Kubota LT: Determination of glutathione in hemolysed erythrocyte with amperometric sensor based on TTF-TCNQ. Clin Chim Acta. 2006 Sep;371(1-2):152-8. Epub 2006 May 2.16650398Calabrese V, Scapagnini G, Ravagna A, Bella R, Butterfield DA, Calvani M, Pennisi G, Giuffrida Stella AM: Disruption of thiol homeostasis and nitrosative stress in the cerebrospinal fluid of patients with active multiple sclerosis: evidence for a protective role of acetylcarnitine. Neurochem Res. 2003 Sep;28(9):1321-8.12938853Sohlenius-Sternbeck AK, Schmidt S: Impaired glutathione-conjugating capacity by cryopreserved human and rat hepatocytes. Xenobiotica. 2005 Jul;35(7):727-36.16316931Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. 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Epub 2006 Jan 19.16427183http://hmdb.ca/system/metabolites/msds/000/000/086/original/HMDB00125.pdf?1358894424Glutathione synthetaseP04425GSHB_ECOLIgshBhttp://ecmdb.ca/proteins/P04425.xmlVitamin B12 transport periplasmic protein BtuEP06610BTUE_ECOLIbtuEhttp://ecmdb.ca/proteins/P06610.xmlGlutathione reductaseP06715GSHR_ECOLIgorhttp://ecmdb.ca/proteins/P06715.xmlGlutathione S-transferaseP0A9D2GST_ECOLIgsthttp://ecmdb.ca/proteins/P0A9D2.xmlArsenate reductaseP0AB96ARSC_ECOLIarsChttp://ecmdb.ca/proteins/P0AB96.xmlLactoylglutathione lyaseP0AC81LGUL_ECOLIgloAhttp://ecmdb.ca/proteins/P0AC81.xmlHydroxyacylglutathione hydrolaseP0AC84GLO2_ECOLIgloBhttp://ecmdb.ca/proteins/P0AC84.xmlBifunctional glutathionylspermidine synthetase/amidaseP0AES0GSP_ECOLIgsphttp://ecmdb.ca/proteins/P0AES0.xmlGamma-glutamyltranspeptidaseP18956GGT_ECOLIggthttp://ecmdb.ca/proteins/P18956.xmlS-formylglutathione hydrolase yeiGP33018SFGH2_ECOLIyeiGhttp://ecmdb.ca/proteins/P33018.xmlS-formylglutathione hydrolase frmBP51025SFGH1_ECOLIfrmBhttp://ecmdb.ca/proteins/P51025.xmlOligopeptide transport system permease protein oppBP0AFH2OPPB_ECOLIoppBhttp://ecmdb.ca/proteins/P0AFH2.xmlOligopeptide transport system permease protein oppCP0AFH6OPPC_ECOLIoppChttp://ecmdb.ca/proteins/P0AFH6.xmlATP-binding/permease protein cydCP23886CYDC_ECOLIcydChttp://ecmdb.ca/proteins/P23886.xmlATP-binding/permease protein cydDP29018CYDD_ECOLIcydDhttp://ecmdb.ca/proteins/P29018.xmlGlutathione transport system permease protein gsiCP75798GSIC_ECOLIgsiChttp://ecmdb.ca/proteins/P75798.xmlGlutathione transport system permease protein gsiDP75799GSID_ECOLIgsiDhttp://ecmdb.ca/proteins/P75799.xmlGlutathione import ATP-binding protein gsiAP75796GSIA_ECOLIgsiAhttp://ecmdb.ca/proteins/P75796.xmlThiol:disulfide interchange protein DsbGP77202DSBG_ECOLIdsbGhttp://ecmdb.ca/proteins/P77202.xmlGlutaredoxin-4P0AC69GLRX4_ECOLIgrxDhttp://ecmdb.ca/proteins/P0AC69.xmlThiol:disulfide interchange protein DsbCP0AEG6DSBC_ECOLIdsbChttp://ecmdb.ca/proteins/P0AEG6.xmlGlutaredoxin-3P0AC62GLRX3_ECOLIgrxChttp://ecmdb.ca/proteins/P0AC62.xmlGlutaredoxin-2P0AC59GLRX2_ECOLIgrxBhttp://ecmdb.ca/proteins/P0AC59.xmlGlutathione-binding protein gsiBP75797GSIB_ECOLIgsiBhttp://ecmdb.ca/proteins/P75797.xmlGlutaredoxin-1P68688GLRX1_ECOLIgrxAhttp://ecmdb.ca/proteins/P68688.xmlGSH-dependent disulfide bond oxidoreductaseP77526yfcGhttp://ecmdb.ca/proteins/P77526.xmlOligopeptide transport system permease protein oppBP0AFH2OPPB_ECOLIoppBhttp://ecmdb.ca/proteins/P0AFH2.xmlOligopeptide transport system permease protein oppCP0AFH6OPPC_ECOLIoppChttp://ecmdb.ca/proteins/P0AFH6.xmlPeptide transport system permease protein sapBP0AGH3SAPB_ECOLIsapBhttp://ecmdb.ca/proteins/P0AGH3.xmlPeptide transport system permease protein sapCP0AGH5SAPC_ECOLIsapChttp://ecmdb.ca/proteins/P0AGH5.xmlDipeptide and tripeptide permease BP36837DTPB_ECOLIdtpBhttp://ecmdb.ca/proteins/P36837.xmlProbable dipeptide and tripeptide permease YjdLP39276YJDL_ECOLIyjdLhttp://ecmdb.ca/proteins/P39276.xmlGlutathione transport system permease protein gsiCP75798GSIC_ECOLIgsiChttp://ecmdb.ca/proteins/P75798.xmlGlutathione transport system permease protein gsiDP75799GSID_ECOLIgsiDhttp://ecmdb.ca/proteins/P75799.xmlDipeptide and tripeptide permease AP77304DTPA_ECOLIdtpAhttp://ecmdb.ca/proteins/P77304.xmlGlutathione import ATP-binding protein gsiAP75796GSIA_ECOLIgsiAhttp://ecmdb.ca/proteins/P75796.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlGlutathione-binding protein gsiBP75797GSIB_ECOLIgsiBhttp://ecmdb.ca/proteins/P75797.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAdenosine triphosphate + Water + Glutathione > ADP + Glutathione + Hydrogen ion + PhosphateRXN0-11Adenosine triphosphate + Water + Glutathione > ADP + Glutathione + Hydrogen ion + PhosphateRXN0-11glutaredoxin + 2 Glutathione > glutaredoxin + Glutathione disulfideS-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ionR00527S-FORMYLGLUTATHIONE-HYDROLASE-RXNArsenate + 2 Glutathione > Arsenite + Glutathione disulfide + WaterWater + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acidR01736GLYOXII-RXNperiplasmic disulfide isomerase/thiol-disulphide oxidase (oxidized) + 2 Glutathione > periplasmic disulfide isomerase/thiol-disulphide oxidase (reduced) + Glutathione disulfideGlutathione + Pyruvaldehyde <> S-LactoylglutathioneR02530GLYOXI-RXN2 Glutathione + Hydrogen peroxide <> Glutathione disulfide +2 WaterR00274GLUTATHIONE-PEROXIDASE-RXNprotein disulfide isomerase II (oxidized) + 2 Glutathione > protein disulfide isomerase II (reduced) + Glutathione disulfideAdenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + PhosphateR00497GLUTATHIONE-SYN-RXNAdenosine triphosphate + Glutathione + Spermidine <> ADP + Glutathionylspermidine + Hydrogen ion + PhosphateR01917GSPSYN-RXNGlutathionylspermidine + Water <> Glutathione + SpermidineR01918GSPAMID-RXNGlutathione + Water > Cysteinylglycine + L-GlutamateR00494Glutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADPR00115GLUTATHIONE-REDUCT-NADPH-RXNFormaldehyde + Glutathione <> S-(Hydroxymethyl)glutathioneRXN-29612 Glutathione + NAD <> Glutathione disulfide + NADH + Hydrogen ionR000942 Glutathione + NADP <> Glutathione disulfide + NADPH + Hydrogen ionR00115Glutathione + Water <> Cysteinylglycine + L-GlutamateR00494Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Phosphate + GlutathioneR00497S-Formylglutathione + Water <> Formic acid + GlutathioneR00527Glutathione + L-Amino acid <> Cysteinylglycine + (5-L-Glutamyl)-L-amino acidR01262S-Lactoylglutathione + Water <> Glutathione + D-Lactic acidR01736GLYOXII-RXNAdenosine triphosphate + Glutathione + Spermidine <> ADP + Phosphate + GlutathionylspermidineR01917S-Lactoylglutathione <> Glutathione + PyruvaldehydeR02530GLYOXI-RXNRX + Glutathione <> Halide + R-S-GlutathioneR03522(1R,2S)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthaleneR07002(1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthaleneR07003(1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthaleneR070041-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthaleneR070231-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthaleneR070241-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthaleneR070251-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthaleneR070262 Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid <> Glutathione disulfide + 5-HETE + WaterR070342 Glutathione + 15(S)-HPETE <> Glutathione disulfide + 15(S)-HETE + WaterR07035Bromobenzene-3,4-oxide + Glutathione <> 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzeneR07069Bromobenzene-2,3-oxide + Glutathione <> 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzeneR07070Benzo[a]pyrene-4,5-oxide + Glutathione <> 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyreneR07083Benzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + WaterR070842,2-Dichloroacetaldehyde + Glutathione <> S-(2,2-Dichloro-1-hydroxy)ethyl glutathioneR070911,1-Dichloroethylene epoxide + Glutathione <> 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acidR070922,2-Dichloroacetaldehyde + Glutathione <> S-(2-Chloroacetyl)glutathione + Hydrochloric acidR070932-(S-Glutathionyl)acetyl chloride + Glutathione <> 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acidR07094Trichloroethene + Glutathione <> S-(1,2-Dichlorovinyl)glutathione + Hydrochloric acidR071001,2-Dibromoethane + Glutathione + Hydrogen ion <> Glutathione episulfonium ion +2 Hydrobromic acidR071132-Bromoacetaldehyde + Glutathione <> S-(Formylmethyl)glutathione + Hydrobromic acidR07116Aldophosphamide + Glutathione <> 4-Glutathionyl cyclophosphamide + WaterR08280Aflatoxin B1-exo-8,9-epoxide + Glutathione <> Aflatoxin B1exo-8,9-epoxide-GSHR09409Selenite + Glutathione + Hydrogen ion > Selenodiglutathione + Glutathione disulfide + WaterRXN-12864Glutathione + Adenosine triphosphate + Water > Glutathione + ADP + Phosphate + Hydrogen ionRXN0-21Glutathione + Adenosine triphosphate + Water > Glutathione + ADP + Phosphate + Hydrogen ionRXN0-212-hydroxyethyldisulfide + Glutathione 2-mercaptoethanol + Glutathione disulfideRXN0-6256bromoacetate + Glutathione Hydrogen ion + glutathione-S-acetate + Br<SUP>-</SUP>RXN0-6549Hydrogen peroxide + Glutathione > Glutathione disulfide + WaterGLUTATHIONE-PEROXIDASE-RXNGlutathione + NADP < Glutathione disulfide + NADPH + Hydrogen ionGLUTATHIONE-REDUCT-NADPH-RXNGlycine + gamma-Glutamylcysteine + Adenosine triphosphate > Hydrogen ion + Glutathione + Phosphate + ADPGLUTATHIONE-SYN-RXNS-Lactoylglutathione < Pyruvaldehyde + GlutathioneGLYOXI-RXNGlutathionylspermidine + Water > Glutathione + SpermidineGSPAMID-RXNSpermidine + Glutathione + Adenosine triphosphate > Hydrogen ion + Glutathionylspermidine + ADP + PhosphateGSPSYN-RXN1-chloro-2,4-dinitrobenzene + Glutathione <> Hydrogen ion + 2,4-dinitrophenyl-S-glutathione + ChlorideGST-RXNS-(Hydroxymethyl)glutathione <> Formaldehyde + GlutathioneRXN-2961S-Formylglutathione + Water > Hydrogen ion + Formic acid + GlutathioneS-FORMYLGLUTATHIONE-HYDROLASE-RXNS-(2-hydroxyacyl)glutathione + Water > Glutathione + a 2-hydroxy carboxylateAdenosine triphosphate + gamma-Glutamylcysteine + Glycine > ADP + Inorganic phosphate + Glutathione2 Glutathione + NADP > Glutathione disulfide + NADPHGlutathione + Spermidine + Adenosine triphosphate > Glutathionylspermidine + ADP + Inorganic phosphateRX + Glutathione > HX + R-S-glutathioneS-Lactoylglutathione > Glutathione + PyruvaldehydeS-Formylglutathione + Water > Glutathione + Formic acidRX + Glutathione <> Halide + R-S-GlutathioneR03522 R08511 R08512 S-(2-Hydroxyacyl)glutathione + Water <> Glutathione + 2-Hydroxy carboxylateR04090 gamma-Glutamylcysteine + Glycine + Adenosine triphosphate > Hydrogen ion + Phosphate + Adenosine diphosphate + Glutathione + ADPPW_R003053Oxidized glutathione + Hydrogen ion + NADPH + Glutathione disulfide + NADPH > NADP +2 GlutathionePW_R003055Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalenePW_R005206Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalenePW_R005207Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalenePW_R005246Glutathione + 1-Nitronaphthalene-5,6-oxide > 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalenePW_R0054061-Nitronaphthalene-5,6-oxide + Glutathione > 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalenePW_R005409Glutathione + 1-Nitronaphthalene-7,8-oxide > 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalenePW_R0054121-Nitronaphthalene-7,8-oxide + Glutathione > 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthalenePW_R005415Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathionePW_R005505Glutathione + Bromobenzene-2,3-oxide > 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzenePW_R005512Glutathione + 2-(S-Glutathionyl)acetyl chloride > 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acidPW_R005816Bromobenzene-3,4-oxide + Glutathione < 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzenePW_R005900Pyruvaldehyde + Glutathione > S-LactoylglutathionePW_R006149S-Lactoylglutathione + Water > Glutathione + Hydrogen ion + L-Lactic acidPW_R006150Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + PhosphateRX + Glutathione <> Halide + R-S-Glutathione1-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthaleneGlutathione + Water > Cysteinylglycine + L-GlutamateGlutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADPGlutathione + Pyruvaldehyde <> S-LactoylglutathioneS-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ionGlutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADPGlutathione + Water > Cysteinylglycine + L-GlutamateGutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture16600.0uM0.037 oCK12 NCM3722Mid-Log Phase664000000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolShake flask and filter culture17600.0uM0.037 oCK12 NCM3722Mid-Log Phase704000000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateShake flask and filter culture7970.0uM0.037 oCK12 NCM3722Mid-Log Phase318800000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.1956162148 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h50.6uM0.037 oCBW25113Stationary Phase, glucose limited2024000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776