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Bovine Metabolome Database



Showing metabocard for Cysteinylglycine (BMDB00078)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:40
Accession Number BMDB00078
Common Name Cysteinylglycine
Description Cysteinylglycine 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)
Synonyms
  1. L-Cysteinylglycine
  2. N-L-Cysteinylglycine
  3. N-L-cysteinyl-Glycine
  4. N-cysteinyl Glycine
  5. N-cysteinyl-Glycine;Cys-Gly
Chemical IUPAC Name 2-(2-amino-3-sulfanyl-propanoyl)aminoacetic acid
Chemical Formula C5H10N2O3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Polypeptides
Sub Class
  • Dipeptides
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); carboxylic acid; secondary carboxylic acid amide; thiol (sulfanyl compound); alkylthiol
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 178.210
Monoisotopic Molecular Weight 178.041214
Isomeric SMILES N[C@@H](CS)C(=O)NCC(O)=O
Canonical SMILES NC(CS)C(=O)NCC(O)=O
KEGG Compound ID C01419 Link Image
BioCyc ID GLUTATHIONE Link Image
BiGG ID 1445980 Link Image
Wikipedia Link Not Available
METLIN ID 5134 Link Image
PubChem Compound 439498 Link Image
PubChem Substance 16178950 Link Image
ChEBI ID Not Available
CAS Registry Number 19246-18-5
InChI Identifier InChI=1/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
Synthesis Reference Holleman, James W. Synthesis of glutathione and cysteinylglycine by soluble enzymes of rat liver. Compt. rend. (1954), 238 1360-1.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.25 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.59 [Predicted by ALOGPS]; -3.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location Not Available
Tissue Location
Tissue References
Most Tissues
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Glutathione Metabolism
HMDB Pathways
Name Glutathione Metabolism
Image Show Link Image
KEGG Pathways
Name Glutathione Metabolism
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SimCell Pathways
Name Glutathione Metabolism
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Graph
SBML
General References Not Available