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N-gamma-L-Glutamyl-L-phenylalanine (FDB000716)

Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2019-11-26 02:55:16 UTC
Primary IDFDB000716
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-gamma-L-Glutamyl-L-phenylalanine
DescriptionN-gamma-L-Glutamyl-L-phenylalanine, also known as gamma-glu-phe or γ-glu-phe, 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. N-gamma-L-Glutamyl-L-phenylalanine is a very strong basic compound (based on its pKa). N-gamma-L-Glutamyl-L-phenylalanine has been detected, but not quantified in, several different foods, such as garlics, garden onions, onion-family vegetables, soft-necked garlics, and pulses. This could make N-gamma-L-glutamyl-L-phenylalanine a potential biomarker for the consumption of these foods.
CAS Number6810-81-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP-2ALOGPS
logP-1.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.73 m³·mol⁻¹ChemAxon
Polarizability29.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H18N2O5
IUPAC name2-amino-4-[(1-carboxy-2-phenylethyl)-C-hydroxycarbonimidoyl]butanoic acid
InChI IdentifierInChI=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)
InChI KeyXHHOHZPNYFQJKL-UHFFFAOYSA-N
Isomeric SMILESNC(CC\C(O)=N\C(CC1=CC=CC=C1)C(O)=O)C(O)=O
Average Molecular Weight294.3031
Monoisotopic Molecular Weight294.121571696
Classification
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
  • Phenylalanine or derivatives
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 6.16%; N 9.52%; O 27.18%DFC
Melting PointMp 164-174° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +17.3 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-gamma-L-Glutamyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9140000000-c57c23cffc4e4006c360Spectrum
Predicted GC-MSN-gamma-L-Glutamyl-L-phenylalanine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9153600000-258d8a8c34be67aa2223Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01r2-0490000000-e5c6ea826b56995bdddf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-1960000000-544f0a89b2472e87525c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07bf-9810000000-4b8b3443a3cf592ea67e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0190000000-22ea80f2c0dd6b7959752015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005d-2590000000-aa3f0699bba79698cf892015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-966dda8c5319c0a100772015-04-25View Spectrum
NMRNot Available
ChemSpider ID485637
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID558649
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29562
CRC / DFC (Dictionary of Food Compounds) IDBCT97-V:BFV93-W
EAFUS IDNot Available
Dr. Duke IDGAMMA-L-GLUTAMYL-PHENYLALANINE|GAMMA-L-GLUTAMYL-L-BETA-PHENYL-BETA-ALANINE|GAMMA-GLUTAMYL-PHENYLALANINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).