Showing metabocard for Glutamylphenylalanine (BMDB0000594)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:18 UTC
Update Date2020-05-11 20:37:15 UTC
BMDB IDBMDB0000594
Secondary Accession Numbers
  • BMDB00594
Metabolite Identification
Common NameGlutamylphenylalanine
Descriptiongamma-Glutamylphenylalanine, also known as L-gamma-glu-L-phe or N-(γ-L-glutamyl)phenylalanine, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review a significant number of articles have been published on gamma-Glutamylphenylalanine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acidChEBI
L-gamma-Glu-L-pheChEBI
L-gamma-Glutamyl-L-phenylalanineChEBI
N-(gamma-L-Glutamyl)phenylalanineChEBI
N-L-gamma-Glutamyl-3-phenyl-L-alanineChEBI
N-L-gamma-Glutamyl-L-phenylalanineChEBI
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoateGenerator
L-g-Glu-L-pheGenerator
L-Γ-glu-L-pheGenerator
L-g-Glutamyl-L-phenylalanineGenerator
L-Γ-glutamyl-L-phenylalanineGenerator
N-(g-L-Glutamyl)phenylalanineGenerator
N-(Γ-L-glutamyl)phenylalanineGenerator
N-L-g-Glutamyl-3-phenyl-L-alanineGenerator
N-L-Γ-glutamyl-3-phenyl-L-alanineGenerator
N-L-g-Glutamyl-L-phenylalanineGenerator
N-L-Γ-glutamyl-L-phenylalanineGenerator
g-GlutamylphenylalanineGenerator
Γ-glutamylphenylalanineGenerator
gamma-Glu-pheMeSH
γ-Glu-PheHMDB, Generator
γ-L-Glu-L-PheHMDB
γ-L-Glutamyl-L-phenylalanineHMDB
N-γ-GlutamylphenylalanineHMDB
N-L-γ-GlutamylphenylalanineHMDB
gamma-L-Glu-L-PheHMDB
gamma-L-Glutamyl-L-phenylalanineHMDB
N-gamma-GlutamylphenylalanineHMDB
N-L-gamma-GlutamylphenylalanineHMDB
H-γ-Glu-Phe-OHHMDB
H-gamma-Glu-Phe-OHHMDB
gamma-GlutamylphenylalanineHMDB, ChEBI
N-gamma-L-Glutamyl-L-phenylalanineHMDB
N-γ-L-Glutamyl-L-phenylalanineHMDB
g-Glu-PheGenerator, HMDB
Chemical FormulaC14H18N2O5
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid
Traditional Namegamma-glutamylphenylalanine
CAS Registry Number7432-24-8
SMILES
N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
InChI KeyXHHOHZPNYFQJKL-QWRGUYRKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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-2.2ALOGPS
logP-2.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.2 m³·mol⁻¹ChemAxon
Polarizability29.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0029562
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112161
KNApSAcK IDNot Available
Chemspider ID99868
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound111299
PDB IDNot Available
ChEBI ID89582
References
Synthesis ReferenceBodnaryk, Robert P. Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine. Insect Biochemistry (1972), 2(1), 49-52.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available