Showing metabocard for 5-L-Glutamyl-L-alanine (BMDB0006248)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:53 UTC
Update Date2020-05-21 16:28:25 UTC
BMDB IDBMDB0006248
Secondary Accession Numbers
  • BMDB06248
Metabolite Identification
Common Name5-L-Glutamyl-L-alanine
Descriptiongamma-Glutamylalanine, also known as 5-L-glutamyl-L-alanine or L-gamma-glu-L-ala, 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. gamma-Glutamylalanine exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on gamma-Glutamylalanine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-L-Glutamyl-L-alanineChEBI
gamma-L-Glutamyl-L-alanineChEBI
L-gamma-Glu-L-alaChEBI
N-L-gamma-Glutamyl-L-alanineChEBI
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
g-GlutamylalanineGenerator
Γ-glutamylalanineGenerator
γ-Glu-AlaHMDB
γ-L-Glu-L-AlaHMDB
L-γ-Glutamyl-L-alanineHMDB
N-γ-GlutamylalanineHMDB
N-L-γ-GlutamylalanineHMDB
gamma-Glu-AlaHMDB
gamma-L-Glu-L-AlaHMDB
L-gamma-Glutamyl-L-alanineHMDB
N-gamma-GlutamylalanineHMDB
N-L-gamma-GlutamylalanineHMDB
gamma-GlutamylalanineHMDB, ChEBI
5-L-GlutamylalanineHMDB
g-Glu-AlaHMDB
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
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
  • 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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006248
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023860
KNApSAcK IDC00055691
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Gamma-glutamylcyclotransferase
General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:
GGCT
Uniprot ID:
Q32LE4
Molecular weight:
21177.0
Reactions
5-L-Glutamyl-L-alanine → Pyroglutamic acid + L-Alaninedetails
Enzyme Details
2. Glutathione hydrolase 6
General function:
Not Available
Specific function:
Cleaves glutathione conjugates.
Gene Name:
GGT6
Uniprot ID:
A7YWM1
Molecular weight:
49626.0
Reactions
Glutathione + L-Alanine → 5-L-Glutamyl-L-alanine + Cysteinylglycinedetails