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Human Metabolome Database Version 3.5

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Showing metabocard for Phenylalanylphenylalanine (HMDB13302)

Record Information
Version 3.5
Creation Date 2009-11-30 08:52:35 -0700
Update Date 2013-02-08 17:30:02 -0700
HMDB ID HMDB13302
Secondary Accession Numbers None
Metabolite Identification
Common Name Phenylalanylphenylalanine
Description Phenylalanylphenylalanine (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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Phenyl-N-(3-phenyl-L-alanyl)-L-alanine
  2. Di-L-phenylalanine
  3. L-Phenylalanyl-L-phenylalanine
  4. Phe-phe
  5. Phenylalanyl-phenylalanine
Chemical Formula C18H20N2O3
Average Molecular Weight 312.363
Monoisotopic Molecular Weight 312.147392516
IUPAC Name 2-(2-amino-3-phenylpropanamido)-3-phenylpropanoic acid
Traditional IUPAC Name phe-phe
CAS Registry Number 2577-40-4
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 Key GKZIWHRNKRBEOH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
Substituents
  • Alpha Amino Acid Or Derivative
  • Amphetamine Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Phenethylamine
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
Direct Parent Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.043 g/L ALOGPS
LogP -0.27 ALOGPS
LogP -0.067 ChemAxon
LogS -3.86 ALOGPS
pKa (strongest acidic) 3.78 ChemAxon
pKa (strongest basic) 8.01 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 92.42 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 87.03 ChemAxon
Polarizability 33.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.03 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029369
KNApSAcK ID Not Available
Chemspider ID 58614 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13302 Link_out
Metagene Link HMDB13302 Link_out
METLIN ID Not Available
PubChem Compound 65104 Link_out
PDB ID Not Available
ChEBI ID 356630 Link_out
References
Synthesis Reference Not 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. Pubmed: 1796831 Link_out