2.02012-05-31 09:56:47 -06002015-09-13 12:56:06 -0600ECMDB00078M2MDB000028CysteinylglycineCysteinylglycine is a naturally occurring dipeptide. It is derived from the breakdown of glutathione (a tripeptide).Cys-GlyL-Cysteinyl-glycineL-CysteinylglycineN-Cysteinyl GlycineN-Cysteinyl-GlycineN-L-Cysteinyl-GlycineN-L-CysteinylglycineC5H10N2O3S178.21178.0412128862-[(2R)-2-amino-3-sulfanylpropanamido]acetic acidCys-Gly19246-18-5N[C@@H](CS)C(=O)NCC(O)=OInChI=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/s1ZUKPVRWZDMRIEO-VKHMYHEASA-NSolidCytosolExtra-organismPeriplasmlogp-2.59logs-1.46solubility6.25e+00 g/llogp-3.9pka_strongest_acidic3.6pka_strongest_basic8.08iupac2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acidaverage_mass178.21mono_mass178.041212886smilesN[C@@H](CS)C(=O)NCC(O)=OformulaC5H10N2O3SinchiInChI=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/s1inchikeyZUKPVRWZDMRIEO-VKHMYHEASA-Npolar_surface_area92.42refractivity41.03polarizability16.97rotatable_bond_count4acceptor_count4donor_count4physiological_charge0formal_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.
PW000833ec00480MetabolicSpecdb::CMs1758Specdb::CMs3141Specdb::CMs30838Specdb::CMs30986Specdb::CMs37284Specdb::CMs173841Specdb::CMs1049659Specdb::CMs1049661Specdb::CMs1049663Specdb::CMs1049664Specdb::CMs1049666Specdb::CMs1049668Specdb::CMs1049670Specdb::NmrOneD142050Specdb::NmrOneD142051Specdb::NmrOneD142052Specdb::NmrOneD142053Specdb::NmrOneD142054Specdb::NmrOneD142055Specdb::NmrOneD142056Specdb::NmrOneD142057Specdb::NmrOneD142058Specdb::NmrOneD142059Specdb::NmrOneD142060Specdb::NmrOneD142061Specdb::NmrOneD142062Specdb::NmrOneD142063Specdb::NmrOneD142064Specdb::NmrOneD142065Specdb::NmrOneD142066Specdb::NmrOneD142067Specdb::NmrOneD142068Specdb::NmrOneD142069Specdb::MsMs28400Specdb::MsMs28401Specdb::MsMs28402Specdb::MsMs34958Specdb::MsMs34959Specdb::MsMs34960Specdb::MsMs448164Specdb::MsMs2232172Specdb::MsMs2234361Specdb::MsMs2234563Specdb::MsMs2328903Specdb::MsMs2328904Specdb::MsMs2328905Specdb::MsMs2634131Specdb::MsMs2634132Specdb::MsMs2634133HMDB00078439498388596C01419CYS-GLYKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Perry TL, Hansen S: Cystinylglycine in plasma: diagnostic relevance for pyroglutamic acidemia, homocystinuria, and phenylketonuria. Clin Chim Acta. 1981 Nov 25;117(1):7-12.7333014Bald E, Glowacki R: Analysis of saliva for glutathione and metabolically related thiols by liquid chromatography with ultraviolet detection. Amino Acids. 2005 Jun;28(4):431-3. 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(1954), 238 1360-1. http://hmdb.ca/system/metabolites/msds/000/000/057/original/HMDB00078.pdf?1358463314Aminopeptidase NP04825AMPN_ECOLIpepNhttp://ecmdb.ca/proteins/P04825.xmlAminoacyl-histidine dipeptidaseP15288PEPD_ECOLIpepDhttp://ecmdb.ca/proteins/P15288.xmlGamma-glutamyltranspeptidaseP18956GGT_ECOLIggthttp://ecmdb.ca/proteins/P18956.xmlPeptidase BP37095PEPB_ECOLIpepBhttp://ecmdb.ca/proteins/P37095.xmlCytosol aminopeptidaseP68767AMPA_ECOLIpepAhttp://ecmdb.ca/proteins/P68767.xmlDipeptide transport system permease protein dppBP0AEF8DPPB_ECOLIdppBhttp://ecmdb.ca/proteins/P0AEF8.xmlDipeptide transport system permease protein dppCP0AEG1DPPC_ECOLIdppChttp://ecmdb.ca/proteins/P0AEG1.xmlOligopeptide transport system permease protein oppBP0AFH2OPPB_ECOLIoppBhttp://ecmdb.ca/proteins/P0AFH2.xmlOligopeptide transport system permease protein oppCP0AFH6OPPC_ECOLIoppChttp://ecmdb.ca/proteins/P0AFH6.xmlDipeptide transport ATP-binding protein dppDP0AAG0DPPD_ECOLIdppDhttp://ecmdb.ca/proteins/P0AAG0.xmlDipeptide transport ATP-binding protein dppFP37313DPPF_ECOLIdppFhttp://ecmdb.ca/proteins/P37313.xmlPeriplasmic dipeptide transport proteinP23847DPPA_ECOLIdppAhttp://ecmdb.ca/proteins/P23847.xmlAminopeptidase NP04825AMPN_ECOLIpepNhttp://ecmdb.ca/proteins/P04825.xmlDipeptide transport system permease protein dppBP0AEF8DPPB_ECOLIdppBhttp://ecmdb.ca/proteins/P0AEF8.xmlDipeptide transport system permease protein dppCP0AEG1DPPC_ECOLIdppChttp://ecmdb.ca/proteins/P0AEG1.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.xmlDipeptide permease DP75742DTPD_ECOLIdtpDhttp://ecmdb.ca/proteins/P75742.xmlDipeptide and tripeptide permease AP77304DTPA_ECOLIdtpAhttp://ecmdb.ca/proteins/P77304.xmlDipeptide transport ATP-binding protein dppDP0AAG0DPPD_ECOLIdppDhttp://ecmdb.ca/proteins/P0AAG0.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlDipeptide transport ATP-binding protein dppFP37313DPPF_ECOLIdppFhttp://ecmdb.ca/proteins/P37313.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlPeriplasmic dipeptide transport proteinP23847DPPA_ECOLIdppAhttp://ecmdb.ca/proteins/P23847.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlCysteinylglycine + Water > L-Cysteine + GlycineR00899RXN-6622Adenosine triphosphate + Water + Cysteinylglycine > ADP + Cysteinylglycine + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Cysteinylglycine > ADP + Cysteinylglycine + Hydrogen ion + PhosphateGlutathione + Water > Cysteinylglycine + L-GlutamateR00494Glutathione + Water <> Cysteinylglycine + L-GlutamateR00494Cysteinylglycine + Water <> L-Cysteine + GlycineR00899Glutathione + L-Amino acid <> Cysteinylglycine + (5-L-Glutamyl)-L-amino acidR01262Glutathione + Water > Cysteinylglycine + L-GlutamateCysteinylglycine + Water > L-Cysteine + GlycineGlutathione + Water > Cysteinylglycine + L-Glutamate