2.0 2012-05-31 13:03:49 -0600 2015-09-13 12:56:09 -0600 ECMDB01049 M2MDB000232 gamma-Glutamylcysteine G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG). &gamma;-glutamylcysteine &gamma;-L-glutamyl-L-cysteine (Des-Gly)-Glutathione 3GC 5-L-Glutamyl-L-cysteine 5-L-Glutamylcysteine g-Glu-cys G-Glutamylcysteine G-L-Glutamyl-L-cysteine Gamma-Glu-cys Gamma-Glutamylcysteine Gamma-L-Glutamyl-L-cysteine H-g-Glu-cys-OH H-gamma-Glu-Cys-OH H-Glu(Cys-OH)-OH H-γ-Glu-cys-OH L-g-Glutamyl-L-cysteine L-g-Glutamylcysteine L-gamma-Glutamyl-L-cysteine L-gamma-Glutamylcysteine L-γ-Glutamyl-L-cysteine L-γ-Glutamylcysteine N-(1-Carboxy-2-mercaptoethyl)-L-Glutamine N-L-g-Glutamyl-L-cysteine N-L-gamma-Glutamyl-L-Cysteine N-L-γ-Glutamyl-L-cysteine XN-L-g-glutamyl-Glutamine XN-L-gamma-glutamyl-Glutamine XN-L-γ-Glutamyl-glutamine γ-Glu-cys γ-Glutamylcysteine γ-L-Glutamyl-L-cysteine C8H14N2O5S 250.272 250.062342258 (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid gamma-glutamylcysteine 636-58-8 N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 RITKHVBHSGLULN-WHFBIAKZSA-N Solid Cytosol logp -2.53 ALOGPS logs -1.98 ALOGPS solubility 2.62e+00 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 1.91 ChemAxon pka_strongest_basic 9.24 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid ChemAxon average_mass 250.272 ChemAxon mono_mass 250.062342258 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O ChemAxon formula C8H14N2O5S ChemAxon inchi InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 ChemAxon inchikey RITKHVBHSGLULN-WHFBIAKZSA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 56.31 ChemAxon polarizability 23.36 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 5 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 Metabolic pathways eco01100 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 Specdb::CMs 698 Specdb::CMs 3015 Specdb::CMs 30722 Specdb::CMs 37904 Specdb::CMs 172234 Specdb::NmrOneD 1636 Specdb::NmrOneD 8382 Specdb::NmrOneD 8383 Specdb::NmrOneD 8384 Specdb::NmrOneD 8385 Specdb::NmrOneD 8386 Specdb::NmrOneD 8387 Specdb::NmrOneD 8388 Specdb::NmrOneD 8389 Specdb::NmrOneD 8390 Specdb::NmrOneD 8391 Specdb::NmrOneD 8392 Specdb::NmrOneD 8393 Specdb::NmrOneD 8394 Specdb::NmrOneD 8395 Specdb::NmrOneD 8396 Specdb::NmrOneD 8397 Specdb::NmrOneD 8398 Specdb::NmrOneD 8399 Specdb::NmrOneD 8400 Specdb::NmrOneD 8401 Specdb::MsMs 1400 Specdb::MsMs 1401 Specdb::MsMs 1402 Specdb::MsMs 5038 Specdb::MsMs 179316 Specdb::MsMs 179317 Specdb::MsMs 179318 Specdb::MsMs 181641 Specdb::MsMs 181642 Specdb::MsMs 181643 Specdb::MsMs 448145 Specdb::MsMs 2252663 Specdb::MsMs 2253828 Specdb::MsMs 2254673 Specdb::MsMs 2255888 Specdb::MsMs 2378503 Specdb::MsMs 2378504 Specdb::MsMs 2378505 Specdb::MsMs 2557701 Specdb::MsMs 2557702 Specdb::MsMs 2557703 Specdb::NmrTwoD 1577 HMDB01049 123938 110467 C00669 17515 L-GAMMA-GLUTAMYLCYSTEINE 3GC Keseler, I. 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(2006), 76pp. http://hmdb.ca/system/metabolites/msds/000/000/943/original/HMDB01049.pdf?1358462188 Glutathione synthetase P04425 GSHB_ECOLI gshB http://ecmdb.ca/proteins/P04425.xml Glutamate--cysteine ligase P0A6W9 GSH1_ECOLI gshA http://ecmdb.ca/proteins/P0A6W9.xml Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate R00894 GLUTCYSLIG-RXN Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate R00497 GLUTATHIONE-SYN-RXN Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Phosphate + Glutathione R00497 Adenosine triphosphate + L-Glutamate + L-Cysteine <> ADP + Phosphate + gamma-Glutamylcysteine R00894 Glycine + gamma-Glutamylcysteine + Adenosine triphosphate > Hydrogen ion + Glutathione + Phosphate + ADP GLUTATHIONE-SYN-RXN L-Cysteine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamylcysteine + Phosphate + ADP GLUTCYSLIG-RXN Adenosine triphosphate + L-Glutamate + L-Cysteine > ADP + Inorganic phosphate + gamma-Glutamylcysteine Adenosine triphosphate + gamma-Glutamylcysteine + Glycine > ADP + Inorganic phosphate + Glutathione L-Glutamic acid + Adenosine triphosphate + L-Cysteine + L-Glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + gamma-Glutamylcysteine + ADP PW_R003052 gamma-Glutamylcysteine + Glycine + Adenosine triphosphate > Hydrogen ion + Phosphate + Adenosine diphosphate + Glutathione + ADP PW_R003053 Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate Adenosine triphosphate + L-Cysteine + L-Glutamate <> ADP + gamma-Glutamylcysteine + Hydrogen ion + Phosphate