2.0 2012-05-31 10:21:27 -0600 2015-09-13 12:56:06 -0600 ECMDB00125 M2MDB000048 Glutathione Glutathione (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. &gamma;-L-glutamyl-L-cysteinyl-glycine 5-L-Glutamyl-L-cysteinylglycine Agifutol S Bakezyme RX Copren Deltathione g-Glutamylcysteinylglycine g-L-Glutamyl-L-cysteinyl-glycine g-L-Glutamyl-L-cysteinylglycine Gamma-Glutamylcysteinylglycine Gamma-L-Glutamyl-L-cysteinyl-glycine Gamma-L-Glutamyl-L-cysteinylglycine Glutathion Glutathionate Glutathione Glutathione red Glutathione reduced Glutathione-SH Glutathionic acid Glutatiol Glutatione Glutide Glutinal GSH Isethion L-g-Glutamyl-L-cysteinyl-glycine L-g-Glutamyl-L-cysteinylglycine L-gamma-Glutamyl-L-cysteinyl-glycine L-gamma-Glutamyl-L-cysteinylglycine L-Glutamyl-L-cysteinylglycine L-Glutathione L-Glutathione reduce L-γ-Glutamyl-L-cysteinyl-glycine L-γ-Glutamyl-L-cysteinylglycine Ledac Neuthion Red. glutathione Reduced glutathione Tathion Tathione Triptide γ-Glutamylcysteinylglycine γ-L-Glutamyl-L-cysteinyl-glycine γ-L-Glutamyl-L-cysteinylglycine C10H17N3O6S 307.323 307.083805981 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid glutathione 70-18-8 N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O 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 RWSXRVCMGQZWBV-WDSKDSINSA-N Solid Cytosol Extra-organism Periplasm logp -2.74 ALOGPS logs -2.54 ALOGPS solubility 8.79e-01 g/l ALOGPS melting_point 195 oC logp -4.9 ChemAxon pka_strongest_acidic 1.94 ChemAxon pka_strongest_basic 9.22 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid ChemAxon average_mass 307.323 ChemAxon mono_mass 307.083805981 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C10H17N3O6S ChemAxon inchi 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 ChemAxon inchikey RWSXRVCMGQZWBV-WDSKDSINSA-N ChemAxon polar_surface_area 158.82 ChemAxon refractivity 69.11 ChemAxon polarizability 29.11 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The 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. PW000833 ec00480 Metabolic Cysteine and methionine metabolism ec00270 Pyruvate metabolism ec00620 Methane metabolism ec00680 Metabolism of xenobiotics by cytochrome P450 ec00980 Drug metabolism - cytochrome P450 ec00982 Arachidonic acid metabolism Delete 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 A1 PW000759 ec00590 Metabolic Microbial metabolism in diverse environments ec01120 ABC transporters ec02010 Metabolic pathways eco01100 Selenium metabolism The 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. PW001894 Metabolic glutathione metabolism II The 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 PW001927 Metabolic glutathione metabolism III The 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. PW002018 Metabolic glutathione biosynthesis GLUTATHIONESYN-PWY glutathione redox reactions II GLUT-REDOX-PWY methylglyoxal degradation I PWY-5386 formaldehyde oxidation II (glutathione-dependent) PWY-1801 Specdb::CMs 348 Specdb::CMs 349 Specdb::CMs 3305 Specdb::CMs 30368 Specdb::CMs 30369 Specdb::CMs 32175 Specdb::CMs 32176 Specdb::CMs 32177 Specdb::CMs 37307 Specdb::CMs 155109 Specdb::CMs 1050923 Specdb::CMs 1050925 Specdb::CMs 1050927 Specdb::CMs 1050929 Specdb::CMs 1050930 Specdb::CMs 1050932 Specdb::CMs 1050934 Specdb::CMs 1050936 Specdb::CMs 1050938 Specdb::CMs 1050940 Specdb::CMs 1050942 Specdb::CMs 1050944 Specdb::CMs 1050946 Specdb::CMs 1050947 Specdb::CMs 1050949 Specdb::NmrOneD 1096 Specdb::NmrOneD 1155 Specdb::NmrOneD 142370 Specdb::NmrOneD 142371 Specdb::NmrOneD 142372 Specdb::NmrOneD 142373 Specdb::NmrOneD 142374 Specdb::NmrOneD 142375 Specdb::NmrOneD 142376 Specdb::NmrOneD 142377 Specdb::NmrOneD 142378 Specdb::NmrOneD 142379 Specdb::NmrOneD 142380 Specdb::NmrOneD 142381 Specdb::NmrOneD 142382 Specdb::NmrOneD 142383 Specdb::NmrOneD 142384 Specdb::NmrOneD 142385 Specdb::NmrOneD 142386 Specdb::NmrOneD 142387 Specdb::NmrOneD 142388 Specdb::NmrOneD 142389 Specdb::NmrOneD 166513 Specdb::MsMs 186 Specdb::MsMs 187 Specdb::MsMs 188 Specdb::MsMs 2947 Specdb::MsMs 2948 Specdb::MsMs 2949 Specdb::MsMs 2950 Specdb::MsMs 2951 Specdb::MsMs 2952 Specdb::MsMs 2953 Specdb::MsMs 2954 Specdb::MsMs 2955 Specdb::MsMs 2956 Specdb::MsMs 2957 Specdb::MsMs 2958 Specdb::MsMs 2959 Specdb::MsMs 2960 Specdb::MsMs 2961 Specdb::MsMs 2962 Specdb::MsMs 2963 Specdb::MsMs 2964 Specdb::MsMs 2965 Specdb::MsMs 2966 Specdb::MsMs 2967 Specdb::MsMs 179877 Specdb::NmrTwoD 1154 HMDB00125 124886 111188 C00051 16856 GLUTATHIONE GTT Glutathione Keseler, I. 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Epub 2006 Jan 19. 16427183 http://hmdb.ca/system/metabolites/msds/000/000/086/original/HMDB00125.pdf?1358894424 Glutathione synthetase P04425 GSHB_ECOLI gshB http://ecmdb.ca/proteins/P04425.xml Vitamin B12 transport periplasmic protein BtuE P06610 BTUE_ECOLI btuE http://ecmdb.ca/proteins/P06610.xml Glutathione reductase P06715 GSHR_ECOLI gor http://ecmdb.ca/proteins/P06715.xml Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml Arsenate reductase P0AB96 ARSC_ECOLI arsC http://ecmdb.ca/proteins/P0AB96.xml Lactoylglutathione lyase P0AC81 LGUL_ECOLI gloA http://ecmdb.ca/proteins/P0AC81.xml Hydroxyacylglutathione hydrolase P0AC84 GLO2_ECOLI gloB http://ecmdb.ca/proteins/P0AC84.xml Bifunctional glutathionylspermidine synthetase/amidase P0AES0 GSP_ECOLI gsp http://ecmdb.ca/proteins/P0AES0.xml Gamma-glutamyltranspeptidase P18956 GGT_ECOLI ggt http://ecmdb.ca/proteins/P18956.xml S-formylglutathione hydrolase yeiG P33018 SFGH2_ECOLI yeiG http://ecmdb.ca/proteins/P33018.xml S-formylglutathione hydrolase frmB P51025 SFGH1_ECOLI frmB http://ecmdb.ca/proteins/P51025.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml ATP-binding/permease protein cydC P23886 CYDC_ECOLI cydC http://ecmdb.ca/proteins/P23886.xml ATP-binding/permease protein cydD P29018 CYDD_ECOLI cydD http://ecmdb.ca/proteins/P29018.xml Glutathione transport system permease protein gsiC P75798 GSIC_ECOLI gsiC http://ecmdb.ca/proteins/P75798.xml Glutathione transport system permease protein gsiD P75799 GSID_ECOLI gsiD http://ecmdb.ca/proteins/P75799.xml Glutathione import ATP-binding protein gsiA P75796 GSIA_ECOLI gsiA http://ecmdb.ca/proteins/P75796.xml Thiol:disulfide interchange protein DsbG P77202 DSBG_ECOLI dsbG http://ecmdb.ca/proteins/P77202.xml Glutaredoxin-4 P0AC69 GLRX4_ECOLI grxD http://ecmdb.ca/proteins/P0AC69.xml Thiol:disulfide interchange protein DsbC P0AEG6 DSBC_ECOLI dsbC http://ecmdb.ca/proteins/P0AEG6.xml Glutaredoxin-3 P0AC62 GLRX3_ECOLI grxC http://ecmdb.ca/proteins/P0AC62.xml Glutaredoxin-2 P0AC59 GLRX2_ECOLI grxB http://ecmdb.ca/proteins/P0AC59.xml Glutathione-binding protein gsiB P75797 GSIB_ECOLI gsiB http://ecmdb.ca/proteins/P75797.xml Glutaredoxin-1 P68688 GLRX1_ECOLI grxA http://ecmdb.ca/proteins/P68688.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml Peptide transport system permease protein sapB P0AGH3 SAPB_ECOLI sapB http://ecmdb.ca/proteins/P0AGH3.xml Peptide transport system permease protein sapC P0AGH5 SAPC_ECOLI sapC http://ecmdb.ca/proteins/P0AGH5.xml Dipeptide and tripeptide permease B P36837 DTPB_ECOLI dtpB http://ecmdb.ca/proteins/P36837.xml Probable dipeptide and tripeptide permease YjdL P39276 YJDL_ECOLI yjdL http://ecmdb.ca/proteins/P39276.xml Glutathione transport system permease protein gsiC P75798 GSIC_ECOLI gsiC http://ecmdb.ca/proteins/P75798.xml Glutathione transport system permease protein gsiD P75799 GSID_ECOLI gsiD http://ecmdb.ca/proteins/P75799.xml Dipeptide and tripeptide permease A P77304 DTPA_ECOLI dtpA http://ecmdb.ca/proteins/P77304.xml Glutathione import ATP-binding protein gsiA P75796 GSIA_ECOLI gsiA http://ecmdb.ca/proteins/P75796.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Glutathione-binding protein gsiB P75797 GSIB_ECOLI gsiB http://ecmdb.ca/proteins/P75797.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Glutathione > ADP + Glutathione + Hydrogen ion + Phosphate RXN0-11 Adenosine triphosphate + Water + Glutathione > ADP + Glutathione + Hydrogen ion + Phosphate RXN0-11 glutaredoxin + 2 Glutathione > glutaredoxin + Glutathione disulfide S-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ion R00527 S-FORMYLGLUTATHIONE-HYDROLASE-RXN Arsenate + 2 Glutathione > Arsenite + Glutathione disulfide + Water Water + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acid R01736 GLYOXII-RXN periplasmic disulfide isomerase/thiol-disulphide oxidase (oxidized) + 2 Glutathione > periplasmic disulfide isomerase/thiol-disulphide oxidase (reduced) + Glutathione disulfide Glutathione + Pyruvaldehyde <> S-Lactoylglutathione R02530 GLYOXI-RXN 2 Glutathione + Hydrogen peroxide <> Glutathione disulfide +2 Water R00274 GLUTATHIONE-PEROXIDASE-RXN protein disulfide isomerase II (oxidized) + 2 Glutathione > protein disulfide isomerase II (reduced) + Glutathione disulfide Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate R00497 GLUTATHIONE-SYN-RXN Adenosine triphosphate + Glutathione + Spermidine <> ADP + Glutathionylspermidine + Hydrogen ion + Phosphate R01917 GSPSYN-RXN Glutathionylspermidine + Water <> Glutathione + Spermidine R01918 GSPAMID-RXN Glutathione + Water > Cysteinylglycine + L-Glutamate R00494 Glutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADP R00115 GLUTATHIONE-REDUCT-NADPH-RXN Formaldehyde + Glutathione <> S-(Hydroxymethyl)glutathione RXN-2961 2 Glutathione + NAD <> Glutathione disulfide + NADH + Hydrogen ion R00094 2 Glutathione + NADP <> Glutathione disulfide + NADPH + Hydrogen ion R00115 Glutathione + Water <> Cysteinylglycine + L-Glutamate R00494 Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Phosphate + Glutathione R00497 S-Formylglutathione + Water <> Formic acid + Glutathione R00527 Glutathione + L-Amino acid <> Cysteinylglycine + (5-L-Glutamyl)-L-amino acid R01262 S-Lactoylglutathione + Water <> Glutathione + D-Lactic acid R01736 GLYOXII-RXN Adenosine triphosphate + Glutathione + Spermidine <> ADP + Phosphate + Glutathionylspermidine R01917 S-Lactoylglutathione <> Glutathione + Pyruvaldehyde R02530 GLYOXI-RXN RX + Glutathione <> Halide + R-S-Glutathione R03522 (1R,2S)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene R07002 (1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene R07003 (1S,2R)-Naphthalene 1,2-oxide + Glutathione <> (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene R07004 1-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthalene R07023 1-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene R07024 1-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene R07025 1-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene R07026 2 Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid <> Glutathione disulfide + 5-HETE + Water R07034 2 Glutathione + 15(S)-HPETE <> Glutathione disulfide + 15(S)-HETE + Water R07035 Bromobenzene-3,4-oxide + Glutathione <> 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene R07069 Bromobenzene-2,3-oxide + Glutathione <> 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene R07070 Benzo[a]pyrene-4,5-oxide + Glutathione <> 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene R07083 Benzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Water R07084 2,2-Dichloroacetaldehyde + Glutathione <> S-(2,2-Dichloro-1-hydroxy)ethyl glutathione R07091 1,1-Dichloroethylene epoxide + Glutathione <> 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid R07092 2,2-Dichloroacetaldehyde + Glutathione <> S-(2-Chloroacetyl)glutathione + Hydrochloric acid R07093 2-(S-Glutathionyl)acetyl chloride + Glutathione <> 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid R07094 Trichloroethene + Glutathione <> S-(1,2-Dichlorovinyl)glutathione + Hydrochloric acid R07100 1,2-Dibromoethane + Glutathione + Hydrogen ion <> Glutathione episulfonium ion +2 Hydrobromic acid R07113 2-Bromoacetaldehyde + Glutathione <> S-(Formylmethyl)glutathione + Hydrobromic acid R07116 Aldophosphamide + Glutathione <> 4-Glutathionyl cyclophosphamide + Water R08280 Aflatoxin B1-exo-8,9-epoxide + Glutathione <> Aflatoxin B1exo-8,9-epoxide-GSH R09409 Selenite + Glutathione + Hydrogen ion > Selenodiglutathione + Glutathione disulfide + Water RXN-12864 Glutathione + Adenosine triphosphate + Water > Glutathione + ADP + Phosphate + Hydrogen ion RXN0-21 Glutathione + Adenosine triphosphate + Water > Glutathione + ADP + Phosphate + Hydrogen ion RXN0-21 2-hydroxyethyldisulfide + Glutathione 2-mercaptoethanol + Glutathione disulfide RXN0-6256 bromoacetate + Glutathione Hydrogen ion + glutathione-S-acetate + Br<SUP>-</SUP> RXN0-6549 Hydrogen peroxide + Glutathione > Glutathione disulfide + Water GLUTATHIONE-PEROXIDASE-RXN Glutathione + NADP < Glutathione disulfide + NADPH + Hydrogen ion GLUTATHIONE-REDUCT-NADPH-RXN Glycine + gamma-Glutamylcysteine + Adenosine triphosphate > Hydrogen ion + Glutathione + Phosphate + ADP GLUTATHIONE-SYN-RXN S-Lactoylglutathione < Pyruvaldehyde + Glutathione GLYOXI-RXN Glutathionylspermidine + Water > Glutathione + Spermidine GSPAMID-RXN Spermidine + Glutathione + Adenosine triphosphate > Hydrogen ion + Glutathionylspermidine + ADP + Phosphate GSPSYN-RXN 1-chloro-2,4-dinitrobenzene + Glutathione <> Hydrogen ion + 2,4-dinitrophenyl-S-glutathione + Chloride GST-RXN S-(Hydroxymethyl)glutathione <> Formaldehyde + Glutathione RXN-2961 S-Formylglutathione + Water > Hydrogen ion + Formic acid + Glutathione S-FORMYLGLUTATHIONE-HYDROLASE-RXN S-(2-hydroxyacyl)glutathione + Water > Glutathione + a 2-hydroxy carboxylate Adenosine triphosphate + gamma-Glutamylcysteine + Glycine > ADP + Inorganic phosphate + Glutathione 2 Glutathione + NADP > Glutathione disulfide + NADPH Glutathione + Spermidine + Adenosine triphosphate > Glutathionylspermidine + ADP + Inorganic phosphate RX + Glutathione > HX + R-S-glutathione S-Lactoylglutathione > Glutathione + Pyruvaldehyde S-Formylglutathione + Water > Glutathione + Formic acid RX + Glutathione <> Halide + R-S-Glutathione R03522 R08511 R08512 S-(2-Hydroxyacyl)glutathione + Water <> Glutathione + 2-Hydroxy carboxylate R04090 gamma-Glutamylcysteine + Glycine + Adenosine triphosphate > Hydrogen ion + Phosphate + Adenosine diphosphate + Glutathione + ADP PW_R003053 Oxidized glutathione + Hydrogen ion + NADPH + Glutathione disulfide + NADPH > NADP +2 Glutathione PW_R003055 Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Glutathionyl-(2R)-hydroxy-1,2-dihydronaphthalene PW_R005206 Naphthalene epoxide + Glutathione + (1R,2S)-Naphthalene 1,2-oxide > (1R)-Hydroxy-(2R)-glutathionyl-1,2-dihydronaphthalene PW_R005207 Glutathione + Naphthalene epoxide + (1R,2S)-Naphthalene 1,2-oxide > (1S)-Hydroxy-(2S)-glutathionyl-1,2-dihydronaphthalene PW_R005246 Glutathione + 1-Nitronaphthalene-5,6-oxide > 1-Nitro-5-glutathionyl-6-hydroxy-5,6-dihydronaphthalene PW_R005406 1-Nitronaphthalene-5,6-oxide + Glutathione > 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene PW_R005409 Glutathione + 1-Nitronaphthalene-7,8-oxide > 1-Nitro-7-glutathionyl-8-hydroxy-7,8-dihydronaphthalene PW_R005412 1-Nitronaphthalene-7,8-oxide + Glutathione > 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthalene PW_R005415 Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathione PW_R005505 Glutathione + Bromobenzene-2,3-oxide > 2,3-Dihydro-2-S-glutathionyl-3-hydroxy bromobenzene PW_R005512 Glutathione + 2-(S-Glutathionyl)acetyl chloride > 2-(S-Glutathionyl)acetyl glutathione + Hydrochloric acid PW_R005816 Bromobenzene-3,4-oxide + Glutathione < 3,4-Dihydro-3-hydroxy-4-S-glutathionyl bromobenzene PW_R005900 Pyruvaldehyde + Glutathione > S-Lactoylglutathione PW_R006149 S-Lactoylglutathione + Water > Glutathione + Hydrogen ion + L-Lactic acid PW_R006150 Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate RX + Glutathione <> Halide + R-S-Glutathione 1-Nitronaphthalene-7,8-oxide + Glutathione <> 1-Nitro-7-hydroxy-8-glutathionyl-7,8-dihydronaphthalene Glutathione + Water > Cysteinylglycine + L-Glutamate Glutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADP Glutathione + Pyruvaldehyde <> S-Lactoylglutathione S-Formylglutathione + Water <> Formic acid + Glutathione + Hydrogen ion Glutathione disulfide + Hydrogen ion + NADPH <>2 Glutathione + NADP Glutathione + Water > Cysteinylglycine + L-Glutamate Gutnick 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 glucose Shake flask and filter culture 16600.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 66400000 0 Bennett, 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. 19561621 Gutnick 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 glycerol Shake flask and filter culture 17600.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 70400000 0 Bennett, 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. 19561621 Gutnick 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 acetate Shake flask and filter culture 7970.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 31880000 0 Bennett, 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. 19561621 48 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 Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 50.6 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 202400 0 Ishii, 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." 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