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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:03:55 UTC
Update Date2020-02-26 21:43:01 UTC
HMDB IDHMDB0029156
Secondary Accession Numbers
  • HMDB0028826
  • HMDB28826
  • HMDB29156
Metabolite Identification
Common NameGlutamylphenylalanine
DescriptionGlutamylphenylalanine is a dipeptide composed of glutamate and phenylalanine, 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. Glutamylphenylalanine 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
Data?1582753381
Synonyms
ValueSource
(4S)-4-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]-C-hydroxycarbonimidoyl}butanoateGenerator
α-Glu-PheHMDB
α-L-Glu-L-PheHMDB
α-GlutamylphenylalanineHMDB
α-L-Glutamyl-L-phenylalanineHMDB
L-α-Glutamyl-L-phenylalanineHMDB
N-α-GlutamylphenylalanineHMDB
N-α-L-Glutamyl-L-phenylalanineHMDB
N-L-α-GlutamylphenylalanineHMDB
N-L-α-Glutamyl-L-phenylalanineHMDB
alpha-Glu-PheHMDB
alpha-L-Glu-L-PheHMDB
alpha-GlutamylphenylalanineHMDB
alpha-L-Glutamyl-L-phenylalanineHMDB
L-alpha-Glutamyl-L-phenylalanineHMDB
N-alpha-GlutamylphenylalanineHMDB
N-alpha-L-Glutamyl-L-phenylalanineHMDB
N-L-alpha-GlutamylphenylalanineHMDB
N-L-alpha-Glutamyl-L-phenylalanineHMDB
4-Amino-N-(α-carboxyphenethyl)-glutaramic acidHMDB
4-Amino-N-(alpha-carboxyphenethyl)-glutaramic acidHMDB
GlutamylphenylalanineHMDB
Glu-PheHMDB
L-Glu-L-PheHMDB
L-Glutamyl-L-phenylalanineHMDB
N-GlutamylphenylalanineHMDB
N-L-Glutamyl-L-phenylalanineHMDB
Glutamyl-phenylalanineHMDB
Glutamic acid phenylalanine dipeptideHMDB
Glutamate phenylalanine dipeptideHMDB
Glutamic acid-phenylalanine dipeptideHMDB
Glutamate-phenylalanine dipeptideHMDB
E-F dipeptideHMDB
EF dipeptideHMDB
Chemical FormulaC14H18N2O5
Average Molecular Weight294.307
Monoisotopic Molecular Weight294.121571688
IUPAC Name(4S)-4-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid
Traditional Nameglutamylphenylalanine
CAS Registry Number20556-22-3
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C14H18N2O5/c15-10(6-7-12(17)18)13(19)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,17,18)(H,20,21)/t10-,11-/m0/s1
InChI KeyXMBSYZWANAQXEV-QWRGUYRKSA-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
  • Phenylalanine or derivatives
  • 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
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Amino fatty acid
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.81Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP-2.2ALOGPS
logP-2.4ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.2 m³·mol⁻¹ChemAxon
Polarizability29.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1290000000-6e7a89e0ccf962fb5e2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4r-7950000000-6c8690dfd7caca35021cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-a0615d4fefd879e5ecddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-555568e3635280fb2f88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r5-1690000000-071b51f05fbd44ebf0abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-024l-6900000000-1519412911f76dca73cdSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18653118
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available