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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-05-22 19:18:26 UTC
Update Date2019-03-14 18:03:16 UTC
HMDB IDHMDB0006248
Secondary Accession Numbers
  • HMDB0029142
  • HMDB0061369
  • HMDB06248
  • HMDB29142
  • HMDB61369
Metabolite Identification
Common Namegamma-Glutamylalanine
Descriptiongamma-Glutamylalanine is a dipeptide composed of gamma-glutamate and alanine, 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. gamma-Glutamylalanine is a natural substrate of the enzyme (5-L-glutamyl)-L-amino acid 5-glutamyltransferase (cyclizing) (g-glutamylcyclotransferase, EC 2.3.2.2) in the glutathione metabolism pathway, which cleaves gamma-glutamylalanine to produce L-5-oxoproline. gamma-Glutamylcyclotransferase is widely distributed in both human and animal tissues where it catalyzes the scission of the y-peptide bonds of many different gamma-glutamyl-amino acids and gamma-glutamyl-gamma-glutamyl-amino acids. The latter are 'better' substrates of the enzyme than the corresponding gamma-glutamyl-amino acids (PMID: 2570694 , 2893631 ).
Structure
Data?1547234351
Synonyms
ValueSource
gamma-GlutamylalanineChEBI
gamma-L-Glutamyl-L-alanineChEBI
L-gamma-Glu-L-alaChEBI
N-L-gamma-Glutamyl-L-alanineChEBI
g-GlutamylalanineGenerator
γ-glutamylalanineGenerator
g-L-Glutamyl-L-alanineGenerator
γ-L-glutamyl-L-alanineGenerator
L-g-Glu-L-alaGenerator
L-γ-glu-L-alaGenerator
N-L-g-Glutamyl-L-alanineGenerator
N-L-γ-glutamyl-L-alanineGenerator
5-L-GlutamylalanineHMDB
g-Glu-alaHMDB
gamma-Glu-alaHMDB
gamma-Glutamylalanine, (D-GLN)-isomerMeSH
γ-Glu-AlaCAS
γ-L-Glu-L-AlaCAS
L-γ-Glutamyl-L-alanineCAS
N-γ-GlutamylalanineCAS
N-L-γ-GlutamylalanineCAS
gamma-L-Glu-L-AlaCAS
L-gamma-Glutamyl-L-alanineCAS
N-gamma-GlutamylalanineCAS
N-L-gamma-GlutamylalanineCAS
5-L-Glutamyl-L-alanineHMDB
N-γ-L-Glutamyl-L-alanineHMDB
N-gamma-L-Glutamyl-L-alanineHMDB
Chemical FormulaC8H14N2O5
Average Molecular Weight218.2072
Monoisotopic Molecular Weight218.090271568
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid
Traditional Nameg-glu-ala
CAS Registry Number5875-41-2
SMILES
C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
InChI KeyWQXXXVRAFAKQJM-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
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alanine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility12.9 g/LALOGPS
logP-3.4ALOGPS
logP-3.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.93ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.59 m³·mol⁻¹ChemAxon
Polarizability20.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00al-9710000000-e2845b73a5e7cd81881fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9332000000-f7980440d2535885b7abJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-2940000000-948d6e9385d802328937JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05br-6900000000-5f1480e854581ee71678JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9200000000-58a633696455e707016dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0690000000-92c8a111979eb46fa59fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06dj-2930000000-1156c919eda2b8e49faeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9200000000-737e76bca1d968721a2aJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023860
KNApSAcK IDNot Available
Chemspider ID389104
KEGG Compound IDC03740
BioCyc IDNot Available
BiGG ID1446127
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440103
PDB IDNot Available
ChEBI ID50619
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. York MJ, Crossley MJ, Hyslop SJ, Fisher ML, Kuchel PW: gamma-Glutamylcyclotransferase: inhibition by D-beta-aminoglutaryl-L-alanine and analysis of the solvent kinetic isotope effect. Eur J Biochem. 1989 Sep 1;184(1):97-101. [PubMed:2570694 ]
  2. Takahashi T, Kondo T, Ohno H, Minato S, Ohshima T, Mikuni S, Soda K, Taniguchi N: A spectrophotometric method for the determination of gamma-glutamyl cyclotransferase with alanine dehydrogenase in the presence of anthglutin. Biochem Med Metab Biol. 1987 Dec;38(3):311-6. [PubMed:2893631 ]