2.0 2012-05-31 09:56:47 -0600 2015-09-13 12:56:06 -0600 ECMDB00078 M2MDB000028 Cysteinylglycine Cysteinylglycine is a naturally occurring dipeptide. It is derived from the breakdown of glutathione (a tripeptide). Cys-Gly L-Cysteinyl-glycine L-Cysteinylglycine N-Cysteinyl Glycine N-Cysteinyl-Glycine N-L-Cysteinyl-Glycine N-L-Cysteinylglycine C5H10N2O3S 178.21 178.041212886 2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid Cys-Gly 19246-18-5 N[C@@H](CS)C(=O)NCC(O)=O InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1 ZUKPVRWZDMRIEO-VKHMYHEASA-N Solid Cytosol Extra-organism Periplasm logp -2.59 ALOGPS logs -1.46 ALOGPS solubility 6.25e+00 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 3.6 ChemAxon pka_strongest_basic 8.08 ChemAxon iupac 2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid ChemAxon average_mass 178.21 ChemAxon mono_mass 178.041212886 ChemAxon smiles N[C@@H](CS)C(=O)NCC(O)=O ChemAxon formula C5H10N2O3S ChemAxon inchi InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1 ChemAxon inchikey ZUKPVRWZDMRIEO-VKHMYHEASA-N ChemAxon polar_surface_area 92.42 ChemAxon refractivity 41.03 ChemAxon polarizability 16.97 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 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 Specdb::CMs 1758 Specdb::CMs 3141 Specdb::CMs 30838 Specdb::CMs 30986 Specdb::CMs 37284 Specdb::CMs 173841 Specdb::CMs 1049659 Specdb::CMs 1049661 Specdb::CMs 1049663 Specdb::CMs 1049664 Specdb::CMs 1049666 Specdb::CMs 1049668 Specdb::CMs 1049670 Specdb::NmrOneD 142050 Specdb::NmrOneD 142051 Specdb::NmrOneD 142052 Specdb::NmrOneD 142053 Specdb::NmrOneD 142054 Specdb::NmrOneD 142055 Specdb::NmrOneD 142056 Specdb::NmrOneD 142057 Specdb::NmrOneD 142058 Specdb::NmrOneD 142059 Specdb::NmrOneD 142060 Specdb::NmrOneD 142061 Specdb::NmrOneD 142062 Specdb::NmrOneD 142063 Specdb::NmrOneD 142064 Specdb::NmrOneD 142065 Specdb::NmrOneD 142066 Specdb::NmrOneD 142067 Specdb::NmrOneD 142068 Specdb::NmrOneD 142069 Specdb::MsMs 28400 Specdb::MsMs 28401 Specdb::MsMs 28402 Specdb::MsMs 34958 Specdb::MsMs 34959 Specdb::MsMs 34960 Specdb::MsMs 448164 Specdb::MsMs 2232172 Specdb::MsMs 2234361 Specdb::MsMs 2234563 Specdb::MsMs 2328903 Specdb::MsMs 2328904 Specdb::MsMs 2328905 Specdb::MsMs 2634131 Specdb::MsMs 2634132 Specdb::MsMs 2634133 HMDB00078 439498 388596 C01419 CYS-GLY Keseler, I. 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(1954), 238 1360-1. http://hmdb.ca/system/metabolites/msds/000/000/057/original/HMDB00078.pdf?1358463314 Aminopeptidase N P04825 AMPN_ECOLI pepN http://ecmdb.ca/proteins/P04825.xml Aminoacyl-histidine dipeptidase P15288 PEPD_ECOLI pepD http://ecmdb.ca/proteins/P15288.xml Gamma-glutamyltranspeptidase P18956 GGT_ECOLI ggt http://ecmdb.ca/proteins/P18956.xml Peptidase B P37095 PEPB_ECOLI pepB http://ecmdb.ca/proteins/P37095.xml Cytosol aminopeptidase P68767 AMPA_ECOLI pepA http://ecmdb.ca/proteins/P68767.xml Dipeptide transport system permease protein dppB P0AEF8 DPPB_ECOLI dppB http://ecmdb.ca/proteins/P0AEF8.xml Dipeptide transport system permease protein dppC P0AEG1 DPPC_ECOLI dppC http://ecmdb.ca/proteins/P0AEG1.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 Dipeptide transport ATP-binding protein dppD P0AAG0 DPPD_ECOLI dppD http://ecmdb.ca/proteins/P0AAG0.xml Dipeptide transport ATP-binding protein dppF P37313 DPPF_ECOLI dppF http://ecmdb.ca/proteins/P37313.xml Periplasmic dipeptide transport protein P23847 DPPA_ECOLI dppA http://ecmdb.ca/proteins/P23847.xml Aminopeptidase N P04825 AMPN_ECOLI pepN http://ecmdb.ca/proteins/P04825.xml Dipeptide transport system permease protein dppB P0AEF8 DPPB_ECOLI dppB http://ecmdb.ca/proteins/P0AEF8.xml Dipeptide transport system permease protein dppC P0AEG1 DPPC_ECOLI dppC http://ecmdb.ca/proteins/P0AEG1.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 Dipeptide permease D P75742 DTPD_ECOLI dtpD http://ecmdb.ca/proteins/P75742.xml Dipeptide and tripeptide permease A P77304 DTPA_ECOLI dtpA http://ecmdb.ca/proteins/P77304.xml Dipeptide transport ATP-binding protein dppD P0AAG0 DPPD_ECOLI dppD http://ecmdb.ca/proteins/P0AAG0.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Dipeptide transport ATP-binding protein dppF P37313 DPPF_ECOLI dppF http://ecmdb.ca/proteins/P37313.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Periplasmic dipeptide transport protein P23847 DPPA_ECOLI dppA http://ecmdb.ca/proteins/P23847.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Cysteinylglycine + Water > L-Cysteine + Glycine R00899 RXN-6622 Adenosine triphosphate + Water + Cysteinylglycine > ADP + Cysteinylglycine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Cysteinylglycine > ADP + Cysteinylglycine + Hydrogen ion + Phosphate Glutathione + Water > Cysteinylglycine + L-Glutamate R00494 Glutathione + Water <> Cysteinylglycine + L-Glutamate R00494 Cysteinylglycine + Water <> L-Cysteine + Glycine R00899 Glutathione + L-Amino acid <> Cysteinylglycine + (5-L-Glutamyl)-L-amino acid R01262 Glutathione + Water > Cysteinylglycine + L-Glutamate Cysteinylglycine + Water > L-Cysteine + Glycine Glutathione + Water > Cysteinylglycine + L-Glutamate