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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-06 21:02:37 UTC
Update Date2017-12-08 23:13:03 UTC
HMDB IDHMDB0028816
Secondary Accession Numbers
  • HMDB28816
Metabolite Identification
Common NameGlutamylcysteine
DescriptionGlutamylcysteine is a dipeptide composed of glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Thumb
Synonyms
ValueSource
e-C DipeptideHMDB
EC dipeptideHMDB
Glu-cysHMDB
Glutamate cysteine dipeptideHMDB
Glutamate-cysteine dipeptideHMDB
L-Glutamyl-L-cysteineHMDB
α-Glu-CysCAS
α-L-Glu-L-CysCAS
α-GlutamylcysteineCAS
α-L-Glutamyl-L-cysteineCAS
L-α-Glutamyl-L-cysteineCAS
N-α-GlutamylcysteineCAS
N-α-L-Glutamyl-L-cysteineCAS
N-L-α-GlutamylcysteineCAS
N-L-α-Glutamyl-L-cysteineCAS
alpha-Glu-CysCAS
alpha-L-Glu-L-CysCAS
alpha-GlutamylcysteineCAS
alpha-L-Glutamyl-L-cysteineCAS
L-alpha-Glutamyl-L-cysteineCAS
N-alpha-GlutamylcysteineCAS
N-alpha-L-Glutamyl-L-cysteineCAS
N-L-alpha-GlutamylcysteineCAS
N-L-alpha-Glutamyl-L-cysteineCAS
GlutamylcysteineHMDB
L-Glu-L-CysHMDB
N-GlutamylcysteineHMDB
N-L-Glutamyl-L-cysteineHMDB
Glutamyl-cysteineHMDB
Glutamic acid cysteine dipeptideHMDB
Glutamic acid-cysteine dipeptideHMDB
Chemical FormulaC8H14N2O5S
Average Molecular Weight250.27
Monoisotopic Molecular Weight250.062342733
IUPAC Name(4S)-4-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional Namegamma-L-glutamyl-L-cysteine
CAS Registry Number21566-73-4
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CS)C(O)=O
InChI Identifier
InChI=1S/C8H14N2O5S/c9-4(1-2-6(11)12)7(13)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,13)(H,11,12)(H,14,15)/t4-,5-/m0/s1
InChI KeyPABVKUJVLNMOJP-WHFBIAKZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Amino fatty acid
  • Fatty amide
  • N-acyl-amine
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Carboxamide group
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxylic acid
  • Alkylthiol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.97Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility6.29 g/LALOGPS
logP-2.6ALOGPS
logP-4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)8.44ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity56.31 m³·mol⁻¹ChemAxon
Polarizability23.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified24.03 +/- 2.60 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8346973
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10171468
PDB IDNot Available
ChEBI ID89701
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zinellu A, Sotgia S, Usai MF, Chessa R, Deiana L, Carru C: Thiol redox status evaluation in red blood cells by capillary electrophoresis-laser induced fluorescence detection. Electrophoresis. 2005 May;26(10):1963-8. [PubMed:15812837 ]
  2. Wunschmann J, Krajewski M, Letzel T, Huber EM, Ehrmann A, Grill E, Lendzian KJ: Dissection of glutathione conjugate turnover in yeast. Phytochemistry. 2010 Jan;71(1):54-61. doi: 10.1016/j.phytochem.2009.09.034. Epub 2009 Nov 10. [PubMed:19897216 ]
  3. Murata M, Bansho Y, Inoue S, Ito K, Ohnishi S, Midorikawa K, Kawanishi S: Requirement of glutathione and cysteine in guanine-specific oxidation of DNA by carcinogenic potassium bromate. Chem Res Toxicol. 2001 Jun;14(6):678-85. [PubMed:11409938 ]
  4. Vande Weghe JG, Ow DW: Accumulation of metal-binding peptides in fission yeast requires hmt2+. Mol Microbiol. 2001 Oct;42(1):29-36. [PubMed:11679064 ]
  5. Zhu YL, Pilon-Smits EA, Tarun AS, Weber SU, Jouanin L, Terry N: Cadmium tolerance and accumulation in Indian mustard is enhanced by overexpressing gamma-glutamylcysteine synthetase. Plant Physiol. 1999 Dec;121(4):1169-78. [PubMed:10594104 ]
  6. Meuwly P, Thibault P, Schwan AL, Rauser WE: Three families of thiol peptides are induced by cadmium in maize. Plant J. 1995 Mar;7(3):391-400. [PubMed:7757112 ]
  7. Yen TY, Villa JA, DeWitt JG: Analysis of phytochelatin-cadmium complexes from plant tissue culture using nano-electrospray ionization tandem mass spectrometry and capillary liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrom. 1999 Sep;34(9):930-41. [PubMed:10491589 ]
  8. Noble DR, Williams DL: Structure-reactivity studies of the Cu(2+)-catalyzed decomposition of four S-nitrosothiols based around the S-Nitrosocysteine/S-nitrosoglutathione structures. Nitric Oxide. 2000 Aug;4(4):392-8. [PubMed:10944424 ]
  9. Brautigam A, Schaumloffel D, Krauss GJ, Wesenberg D: Analytical approach for characterization of cadmium-induced thiol peptides--a case study using Chlamydomonas reinhardtii. Anal Bioanal Chem. 2009 Nov;395(6):1737-47. doi: 10.1007/s00216-009-2921-7. Epub 2009 Jul 10. [PubMed:19590857 ]
  10. Wang W, Clarkson TW, Ballatori N: gamma-Glutamyl transpeptidase and l-cysteine regulate methylmercury uptake by HepG2 cells, a human hepatoma cell line. Toxicol Appl Pharmacol. 2000 Oct 1;168(1):72-8. [PubMed:11000102 ]
  11. Kataoka H, Takagi K, Makita M: Determination of glutathione and related aminothiols by gas chromatography with flame photometric detection. Biomed Chromatogr. 1995 Mar-Apr;9(2):85-9. [PubMed:7795391 ]
  12. Sherrill C, Fahey RC: Import and metabolism of glutathione by Streptococcus mutans. J Bacteriol. 1998 Mar;180(6):1454-9. [PubMed:9515913 ]
  13. Suto RK, Brasch NE, Anderson OP, Finke RG: Synthesis, characterization, solution stability, and X-ray crystal structure of the thiolatocobalamin gamma-glutamylcysteinylcobalamin, a dipeptide analogue of glutathionylcobalamin: insights into the enhanced Co-S bond stability of the natural product glutathionylcobalamin. Inorg Chem. 2001 Jun 4;40(12):2686-92. [PubMed:11375680 ]
  14. Chen WJ, Graminski GF, Armstrong RN: Dissection of the catalytic mechanism of isozyme 4-4 of glutathione S-transferase with alternative substrates. Biochemistry. 1988 Jan 26;27(2):647-54. [PubMed:3349053 ]
  15. Blum R, Meyer KC, Wunschmann J, Lendzian KJ, Grill E: Cytosolic action of phytochelatin synthase. Plant Physiol. 2010 May;153(1):159-69. doi: 10.1104/pp.109.149922. Epub 2010 Mar 19. [PubMed:20304971 ]
  16. Jez JM, Cahoon RE, Chen S: Arabidopsis thaliana glutamate-cysteine ligase: functional properties, kinetic mechanism, and regulation of activity. J Biol Chem. 2004 Aug 6;279(32):33463-70. Epub 2004 Jun 4. [PubMed:15180996 ]
  17. (). Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5. .