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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:31 UTC
HMDB IDHMDB0000709
Secondary Accession Numbers
  • HMDB00709
Metabolite Identification
Common NameL-Cysteinylglycine disulfide
DescriptionL-Cysteinylglycine disulfide, also known as cystinyl-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. L-Cysteinylglycine disulfide is a very strong basic compound (based on its pKa).
Structure
Data?1582752151
Synonyms
ValueSource
L-Cysteinylglycine disulphideGenerator
(R)-N-(3-((2-Amino-2-carboxyethyl)dithio)-ala)-glyHMDB
3-[[2-Amino-2-[(carboxymethyl)carbamoyl]ethyl]dithio]-alanineHMDB
Cystinyl-glyHMDB
CystinylglycineHMDB
L-Cysteinyl-glycine disulfideHMDB
(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulfanyl)propanoateHMDB
(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulphanyl)propanoateHMDB
(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulphanyl)propanoic acidHMDB
Chemical FormulaC8H15N3O5S2
Average Molecular Weight297.352
Monoisotopic Molecular Weight297.045311985
IUPAC Name(2R)-2-amino-3-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}disulfanyl)propanoic acid
Traditional Name(2R)-2-amino-3-{[2-amino-2-(carboxymethylcarbamoyl)ethyl]disulfanyl}propanoic acid
CAS Registry Number70555-24-7
SMILES
N[C@@H](CSSCC(N)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C8H15N3O5S2/c9-4(7(14)11-1-6(12)13)2-17-18-3-5(10)8(15)16/h4-5H,1-3,9-10H2,(H,11,14)(H,12,13)(H,15,16)/t4?,5-/m0/s1
InChI KeyZHRLECIZINSPKL-AKGZTFGVSA-N
Chemical Taxonomy
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
  • L-cysteine-s-conjugate
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Organic disulfide
  • Amino acid or derivatives
  • Dialkyldisulfide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Sulfenyl compound
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Organosulfur compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility6.47 g/LALOGPS
logP-4ALOGPS
logP-7ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.74 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.68 m³·mol⁻¹ChemAxon
Polarizability28.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7o-9430000000-e9e0ab70f09785eaa562Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xs-6595000000-2cbf51cceb6d9ca07827Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7k-2490000000-85bfb9a5b0650bb485c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dj-9620000000-3f76a6be3a823ac22a50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9500000000-9e6a2740d7fceae8ed9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1590000000-d5fe610ebc224e6eebccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-4910000000-dbf0c1f4bd15b89f05c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9410000000-daf70a655049011a0714Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.6 +/- 3.6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<16 uMAdolescent (13-18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30 uMAdolescent (13-18 years old)MaleCystinylglycinuria details
UrineDetected and Quantified49-72 umol/mmol creatinineAdolescent (13-18 years old)MaleCystinylglycinuria details
Associated Disorders and Diseases
Disease References
Cystinylglycinuria
  1. Bellet H, Rejou F, Vallat C, Mion H, Dimeglio A: Cystinylglycinuria: a new neurometabolic disorder? J Inherit Metab Dis. 1999 May;22(3):231-4. [PubMed:10384375 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022195
KNApSAcK IDNot Available
Chemspider ID17215992
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5677
PubChem Compound22833544
PDB IDNot Available
ChEBI ID89930
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceWeygand, Friedrich; Zumach, Gerhard. Synthesis of cystine peptides by dehydrogenation with vicinal dihalogen derivatives. Zeitschrift fuer Naturforschung (1962), 17b 807-10. CODEN: ZNTFA2 ISSN:0372-9516. CAN 59:3854 AN 1963:403854
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:7333014 ]