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Showing Compound Cysteinylglycine (FDB021891)

Record Information
Version1.0
Creation date2011-09-21 00:04:40 UTC
Update date2020-09-17 15:38:16 UTC
Primary IDFDB021891
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCysteinylglycine
DescriptionCysteinylglycine, also known as CG or cys-gly, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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. Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. 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. It is derived from the breakdown of glutathione (a tripeptide). Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans. 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). Outside of the human body, Cysteinylglycine has been detected, but not quantified in, several different foods, such as garlics, sweet rowanberries, butternut squash, common oregano, and pepper (c. frutescens). This could make cysteinylglycine a potential biomarker for the consumption of these foods. Cysteinylglycine, with regard to humans, has been linked to the inborn metabolic disorder phenylketonuria.
CAS Number19246-18-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.25 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.03 m³·mol⁻¹ChemAxon
Polarizability16.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10N2O3S
IUPAC name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
InChI IdentifierInChI=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 KeyZUKPVRWZDMRIEO-VKHMYHEASA-N
Isomeric SMILESN[C@@H](CS)C(=O)NCC(O)=O
Average Molecular Weight178.21
Monoisotopic Molecular Weight178.041212886
Classification
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCysteinylglycine, 3 TMS, GC-MS Spectrumsplash10-00di-2980000000-043097e8f1f3f47ff51fSpectrum
GC-MSCysteinylglycine, non-derivatized, GC-MS Spectrumsplash10-00di-9440000000-ff8b27f3afc92193d83aSpectrum
GC-MSCysteinylglycine, non-derivatized, GC-MS Spectrumsplash10-00di-2980000000-043097e8f1f3f47ff51fSpectrum
Predicted GC-MSCysteinylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9200000000-bae23059b39c80a574a5Spectrum
Predicted GC-MSCysteinylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-8920000000-1b3a6e358d6996916b0eSpectrum
Predicted GC-MSCysteinylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCysteinylglycine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9700000000-6fba6043a24b724b037e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-50e069074067c9f120bd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9100000000-ab3327c5b13829ea6d352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9700000000-9021340a904a56f317cc2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5900000000-b9a1082799c427caf10b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-2b99992e97c6ecb4567b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9000000000-a8b591f7522fe16637fb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-0173b5cf52bb61095c3a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gl-7900000000-f8dc26c3e8b8ec327fc42015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kh9-9100000000-410b0cc1b5e3f850b5052015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0096-5900000000-55967cd7162376aa6fa22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9200000000-5aab410f2c44502defce2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-e0ae26ebba3eeba905da2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-9400000000-1878c834f39272d5af422021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9100000000-0899c0bce2addb667ccb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-05f619b00f6286d67d212021-09-23View Spectrum
NMRNot Available
ChemSpider ID388596
ChEMBL IDCHEMBL371579
KEGG Compound IDC01419
Pubchem Compound ID439498
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00078
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1445980
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference