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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:07:06 UTC
HMDB IDHMDB00078
Secondary Accession NumbersNone
Metabolite Identification
Common NameCysteinylglycine
DescriptionCysteinylglycine is a naturally occurring dipeptide. It is derived from the breakdown of glutathione (a tripeptide). In plasma, cysteinylglycine is in a reduced, oxidized and protein-bound form (aminothiol) and interact via redox and disulphide exchange reactions, in a dynamic system referred to as redox thiol status (PMID 8642471 ). Spermatozoa of sub fertile men contain significantly higher thiol concentrations as compared with those of fertile men. The detrimental effect on embryo quality of a high homocysteine (Hcy, another member of the thiol group) concentration in the ejaculate and in follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome (PMID 16556671 ). Rheumatoid arthritis (RA) is a chronic inflammatory disease which involves the synovial membrane of multiple diarthroidal joints causing damage to cartilage and bones. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols (PMID 15895891 ). Imipenem (thienamycin formamidine), is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized (PMID 15843241 ).
Structure
Thumb
Synonyms
ValueSource
Cys-glyChEBI
CysteinylglycineChEBI
N-L-CysteinylglycineChEBI
N-Cysteinyl glycineHMDB
N-Cysteinyl-glycineHMDB
N-L-Cysteinyl-glycineHMDB
Chemical FormulaC5H10N2O3S
Average Molecular Weight178.21
Monoisotopic Molecular Weight178.041212886
IUPAC Name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
Traditional Namecysteinylglycine
CAS Registry Number19246-18-5
SMILES
N[C@@H](CS)C(=O)NCC(O)=O
InChI Identifier
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
InChI KeyInChIKey=ZUKPVRWZDMRIEO-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.25 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)8.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.03 m3·mol-1ChemAxon
Polarizability16.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2980000000-043097e8f1f3f47ff51fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5900000000-b9a1082799c427caf10bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-2b99992e97c6ecb4567bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9000000000-a8b591f7522fe16637fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-0173b5cf52bb61095c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gl-7900000000-f8dc26c3e8b8ec327fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kh9-9100000000-410b0cc1b5e3f850b505View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Most Tissues
Pathways
NameSMPDB LinkKEGG Link
5-oxoprolinase deficiencySMP00500Not Available
5-OxoprolinuriaSMP00143Not Available
Gamma-glutamyl-transpeptidase deficiencySMP00501Not Available
Gamma-Glutamyltransferase DeficiencySMP00183Not Available
Glutathione MetabolismSMP00015map00480
Glutathione Synthetase DeficiencySMP00337Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified65.7 +/- 4.6 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified13.6 +/- 3.6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified51.7 +/- 1.7 uMInfant (0-1 year old)MaleNormal details
BloodDetected and Quantified63.4 +/- 7.4 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified54.0 +/- 18.8 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified56.0 +/- 7.0 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified51.8 +/- 4.9 uMInfant (0-1 year old)FemaleNormal details
BloodDetected and Quantified57.5 +/- 5.9 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified53.2 +/- 7.7 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.31 (0.99-3.62) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.40 +/- 0.08 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified6.05 +/- 5.12 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified4.73 +/- 2.33 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.6 (0.28-1.54) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.48 +/- 0.15 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.0 (2.0-10.0) uMAdult (>18 years old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Perry TL, Hansen S: Cystinylglycine in plasma: diagnostic relevance for pyroglutamic acidemia, homocystinuria, and phenylketonuria. Clin Chim Acta. 1981 Nov 25;117(1):7-12. [7333014 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021891
KNApSAcK IDNot Available
Chemspider ID388596
KEGG Compound IDC01419
BioCyc IDGLUTATHIONE
BiGG ID1445980
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00078
Metagene LinkHMDB00078
METLIN ID5134
PubChem Compound439498
PDB IDNot Available
ChEBI ID4047
References
Synthesis ReferenceHolleman, James W. Synthesis of glutathione and cysteinylglycine by soluble enzymes of rat liver. Compt. rend. (1954), 238 1360-1.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Perry TL, Hansen S: Cystinylglycine in plasma: diagnostic relevance for pyroglutamic acidemia, homocystinuria, and phenylketonuria. Clin Chim Acta. 1981 Nov 25;117(1):7-12. [7333014 ]
  2. Bald 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. Epub 2005 May 20. [15900404 ]
  3. Reddy VB, Doss GA, Creighton M, Kochansky CJ, Vincent SH, Franklin RB, Karanam BV: Identification and metabolism of a novel dihydrohydroxy-S-glutathionyl conjugate of a peroxisome proliferator-activated receptor agonist, MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromet hyl) phenyl]methyl]benzamide], in rats. Drug Metab Dispos. 2004 Oct;32(10):1154-61. Epub 2004 Jun 30. [15229171 ]
  4. Pastore A, Massoud R, Motti C, Lo Russo A, Fucci G, Cortese C, Federici G: Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Clin Chem. 1998 Apr;44(4):825-32. [9554495 ]
  5. Mansoor MA, Svardal AM, Ueland PM: Determination of the in vivo redox status of cysteine, cysteinylglycine, homocysteine, and glutathione in human plasma. Anal Biochem. 1992 Feb 1;200(2):218-29. [1632485 ]
  6. Fiskerstrand T, Refsum H, Kvalheim G, Ueland PM: Homocysteine and other thiols in plasma and urine: automated determination and sample stability. Clin Chem. 1993 Feb;39(2):263-71. [8432015 ]
  7. Raijmakers MT, Roes EM, Zusterzeel PL, Steegers EA, Peters WH: Thiol status and antioxidant capacity in women with a history of severe pre-eclampsia. BJOG. 2004 Mar;111(3):207-12. [14961880 ]
  8. Duman BS, Ozturk M, Yilmazeri S, Hatemi H: Thiols, malonaldehyde and total antioxidant status in the Turkish patients with type 2 diabetes mellitus. Tohoku J Exp Med. 2003 Nov;201(3):147-55. [14649736 ]
  9. Van Hove JL, Lazeyras F, Zeisel SH, Bottiglieri T, Hyland K, Charles HC, Gray L, Jaeken J, Kahler SG: One-methyl group metabolism in non-ketotic hyperglycinaemia: mildly elevated cerebrospinal fluid homocysteine levels. J Inherit Metab Dis. 1998 Dec;21(8):799-811. [9870205 ]
  10. Josch C, Sies H, Akerboom TP: Hepatic mercapturic acid formation: involvement of cytosolic cysteinylglycine S-conjugate dipeptidase activity. Biochem Pharmacol. 1998 Sep 15;56(6):763-71. [9751082 ]
  11. Jacobsen DW, Gatautis VJ, Green R, Robinson K, Savon SR, Secic M, Ji J, Otto JM, Taylor LM Jr: Rapid HPLC determination of total homocysteine and other thiols in serum and plasma: sex differences and correlation with cobalamin and folate concentrations in healthy subjects. Clin Chem. 1994 Jun;40(6):873-81. [8087981 ]
  12. Zinellu A, Carru C, Galistu F, Usai MF, Pes GM, Baggio G, Federici G, Deiana L: N-methyl-D-glucamine improves the laser-induced fluorescence capillary electrophoresis performance in the total plasma thiols measurement. Electrophoresis. 2003 Aug;24(16):2796-804. [12929176 ]
  13. Zappacosta B, Manni A, Persichilli S, Scribano D, Minucci A, Lazzaro D, De Sole P, Giardina B: HPLC analysis of some sulphur compounds in saliva: comparison between healthy subjects and periodontopathic patients. Clin Chim Acta. 2003 Dec;338(1-2):57-60. [14637266 ]
  14. Andersson A, Isaksson A, Brattstrom L, Hultberg B: Homocysteine and other thiols determined in plasma by HPLC and thiol-specific postcolumn derivatization. Clin Chem. 1993 Aug;39(8):1590-7. [8353942 ]
  15. Kagedal B, Kallberg M: Cysteinylglycine in urine determined by high-performance liquid chromatography. J Chromatogr. 1984 Jun 8;308:75-82. [6746837 ]
  16. Ueland PM, Mansoor MA, Guttormsen AB, Muller F, Aukrust P, Refsum H, Svardal AM: Reduced, oxidized and protein-bound forms of homocysteine and other aminothiols in plasma comprise the redox thiol status--a possible element of the extracellular antioxidant defense system. J Nutr. 1996 Apr;126(4 Suppl):1281S-4S. [8642471 ]
  17. Ebisch IM, Peters WH, Thomas CM, Wetzels AM, Peer PG, Steegers-Theunissen RP: Homocysteine, glutathione and related thiols affect fertility parameters in the (sub)fertile couple. Hum Reprod. 2006 Jul;21(7):1725-33. Epub 2006 Mar 23. [16556671 ]
  18. Giustarini D, Lorenzini S, Rossi R, Chindamo D, Di Simplicio P, Marcolongo R: Altered thiol pattern in plasma of subjects affected by rheumatoid arthritis. Clin Exp Rheumatol. 2005 Mar-Apr;23(2):205-12. [15895891 ]
  19. Badiou S, Bellet H, Lehmann S, Cristol JP, Jaber S: Elevated plasma cysteinylglycine levels caused by cilastatin-associated antibiotic treatment. Clin Chem Lab Med. 2005;43(3):332-4. [15843241 ]

Enzymes

General function:
Involved in proteolysis
Specific function:
Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and IV, neuropeptides, and chemokines. Found to cleave antigen peptides bound to major histocompatibility complex class II molecules of presenting cells and to degrade neurotransmitters at synaptic junctions. Is also implicated as a regulator of IL-8 bioavailability in the endometrium, and therefore may contribute to the regulation of angiogenesis. Is used as a marker for acute myeloid leukemia and plays a role in tumor invasion. In case of human coronavirus 229E (HCoV-229E) infection, serves as receptor for HCoV-229E spike glycoprotein. Mediates as well human cytomegalovirus (HCMV) infection.
Gene Name:
ANPEP
Uniprot ID:
P15144
Molecular weight:
Not Available
Reactions
Cysteinylglycine + Water → L-Cysteine + Glycinedetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails
Glutathione + L-Amino acid → Cysteinylglycine + (5-L-Glutamyl)-L-amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails
Glutathione + L-Amino acid → Cysteinylglycine + (5-L-Glutamyl)-L-amino aciddetails
General function:
Involved in aminopeptidase activity
Specific function:
Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides.
Gene Name:
LAP3
Uniprot ID:
P28838
Molecular weight:
Not Available
Reactions
Cysteinylglycine + Water → L-Cysteine + Glycinedetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails
Glutathione + L-Amino acid → Cysteinylglycine + (5-L-Glutamyl)-L-amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Not Available
Gene Name:
GGT7
Uniprot ID:
A0PJJ9
Molecular weight:
62565.3
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails
Glutathione + L-Amino acid → Cysteinylglycine + (5-L-Glutamyl)-L-amino aciddetails
General function:
Not Available
Specific function:
Initiates extracellular glutathione (GSH) breakdown; catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors (By similarity).
Gene Name:
GGT2
Uniprot ID:
P36268
Molecular weight:
Not Available
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails
General function:
Not Available
Specific function:
Initiates extracellular glutathione (GSH) breakdown; catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors (By similarity).
Gene Name:
GGT3P
Uniprot ID:
A6NGU5
Molecular weight:
Not Available
Reactions
Glutathione + Water → Cysteinylglycine + L-Glutamic aciddetails