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Record Information
Version3.6
Creation Date2009-11-30 15:52:35 UTC
Update Date2017-03-02 21:32:48 UTC
HMDB IDHMDB13302
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylalanylphenylalanine
DescriptionPhenylalanylphenylalanine (Phe-Phe) is a peptide made of two phenylalanine molecules. Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. The Phe-Phe recognition motif of the Alzheimer's Abeta peptide is the smallest peptide able to assemble into higher -order structures.(PMC:1796831).
Structure
Thumb
Synonyms
ValueSource
3-Phenyl-N-(3-phenyl-L-alanyl)-L-alanineHMDB
Di-L-phenylalanineHMDB
L-Phenylalanyl-L-phenylalanineHMDB
Phe-pheHMDB
Phenylalanyl-phenylalanineHMDB
Phenylalanylphenylalanine, (D,D)-isomerMeSH
Phenylalanylphenylalanine monohydrochloride, (L,L)-isomerMeSH
Chemical FormulaC18H20N2O3
Average Molecular Weight312.363
Monoisotopic Molecular Weight312.147392516
IUPAC Name2-(2-amino-3-phenylpropanamido)-3-phenylpropanoic acid
Traditional Namephe-phe
CAS Registry Number2577-40-4
SMILES
NC(CC1=CC=CC=C1)C(=O)NC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C18H20N2O3/c19-15(11-13-7-3-1-4-8-13)17(21)20-16(18(22)23)12-14-9-5-2-6-10-14/h1-10,15-16H,11-12,19H2,(H,20,21)(H,22,23)
InChI KeyGKZIWHRNKRBEOH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and 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
Water Solubility0.043 mg/mLALOGPS
logP-0.27ALOGPS
logP-0.067ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.03 m3·mol-1ChemAxon
Polarizability33.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.03 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029369
KNApSAcK IDNot Available
Chemspider ID58614
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13302
Metagene LinkHMDB13302
METLIN IDNot Available
PubChem Compound65104
PDB IDNot Available
ChEBI ID356630
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. [No authors listed][Proceedings of the Swiss Society of Gynecology and Obstetrics, annual meeting. Interlaken, 13-15 June 1991] Arch Gynecol Obstet. 1991;249 Suppl:S1-189. [1796831 ]