Phenylalanylphenylalanine (CHEM021906)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:15:20 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021906
Identification
Common NamePhenylalanylphenylalanine
ClassSmall Molecule
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)
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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)-isomerHMDB
Phenylalanylphenylalanine monohydrochloride, (L,L)-isomerHMDB
2-[(2-Amino-1-hydroxy-3-phenylpropylidene)amino]-3-phenylpropanoateGenerator
PhenylalanylphenylalanineMeSH
Chemical FormulaC18H20N2O3
Average Molecular Mass312.363 g/mol
Monoisotopic Mass312.147 g/mol
CAS Registry Number2577-40-4
IUPAC Name2-(2-amino-3-phenylpropanamido)-3-phenylpropanoic acid
Traditional Namephe-phe
SMILESNC(CC1=CC=CC=C1)C(=O)NC(CC1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-5940000000-6bf28a0a5a9cfcba9463Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6911000000-52e2592f30d82edb8045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0944000000-1128dcf297fb0a9f2f58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-0910000000-c492baf7e71c23e8749dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9700000000-6558336c17b95fd82a7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0369000000-6698e1e30d8fe0c4b79fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-1972000000-c020c0e9e28eebb79458Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0301-7900000000-7278bfc815cff9474c71Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013302
FooDB IDFDB029369
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID58614
ChEBI ID356630
PubChem Compound ID65104
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.