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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:52:35 UTC
Update Date2017-12-07 02:39:53 UTC
HMDB IDHMDB0013302
Secondary Accession Numbers
  • HMDB13302
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
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.03 m³·mol⁻¹ChemAxon
Polarizability33.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-5940000000-6bf28a0a5a9cfcba9463View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6911000000-52e2592f30d82edb8045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0944000000-1128dcf297fb0a9f2f58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-0910000000-c492baf7e71c23e8749dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9700000000-6558336c17b95fd82a7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0369000000-6698e1e30d8fe0c4b79fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-1972000000-c020c0e9e28eebb79458View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0301-7900000000-7278bfc815cff9474c71View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not SpecifiedBoth
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected and Quantified0.03 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    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
    METLIN IDNot Available
    PubChem Compound65104
    PDB IDNot Available
    ChEBI ID356630
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Authors unspecified: [Proceedings of the Swiss Society of Gynecology and Obstetrics, annual meeting. Interlaken, 13-15 June 1991]. Arch Gynecol Obstet. 1991;249 Suppl:S1-189. [PubMed:1796831 ]