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Phenylalanyl-Arginine

July 21, 2017
Common Name

Phenylalanyl-Arginine Description

Phenylalanyl-Arginine is a dipeptide composed of phenylalanine and arginine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB28989 (Phenylalanyl-Arginine)

Synonyms

Value Source F-R DipeptideHMDB FR DipeptideHMDB L-Phenylalanyl-L-arginineHMDB Phe-argHMDB Phenylalanine arginine dipeptideHMDB Phenylalanine-arginine dipeptideHMDB PhenylalanylarginineHMDB Phenylalanylarginine, D-arg-L-pheMeSH Phenylalanylarginine, all D-isomersMeSH Phenylalanylarginine, L-arg-D-pheMeSH

Chemical Formlia

C15H23N5O3 Average Molecliar Weight

321.3748 Monoisotopic Molecliar Weight

321.180089627 IUPAC Name

2-(2-amino-3-phenylpropanamido)-5-carbamimidamidopentanoic acid Traditional Name

2-(2-amino-3-phenylpropanamido)-5-carbamimidamidopentanoic acid CAS Registry Number

Not Available SMILES

NC(CC1=CC=CC=C1)C(=O)NC(CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C15H23N5O3/c16-11(9-10-5-2-1-3-6-10)13(21)20-12(14(22)23)7-4-8-19-15(17)18/h1-3,5-6,11-12H,4,7-9,16H2,(H,20,21)(H,22,23)(H4,17,18,19)

InChI Key

OZILORBBPKKGRI-UHFFFAOYSA-N Chemical Taxonomy Description

This 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Phenylalanine and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Amphetamines and derivatives
  • Aralkylamines
  • Fatty amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Guanidines
  • Propargyl-type 1,3-dipolar organic compounds
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Carboximidamides
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Guanidine
  • Secondary carboxylic acid amide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-2.02Extrapolated

    Predicted Properties

    Property Value Source Water Solubility0.17 mg/mLALOGPS logP-3.1ALOGPS logP-2ChemAxon logS-3.3ALOGPS pKa (Strongest Acidic)3.66ChemAxon pKa (Strongest Basic)12.09ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area154.32 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity95.84 m3·mol-1ChemAxon Polarizability34.48 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB28989 Metagene Link

    HMDB28989 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: (E)-[6]-Dehydroparadol

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Schug KA, Lindner W, Lemr K: Isomeric discrimination of arginine-containing dipeptides using electrospray ionization-ion trap mass spectrometry and the kinetic method. J Am Soc Mass Spectrom. 2004 Jun;15(6):840-7. [PubMed:15144973 ]
    2. Hawthorne SJ, Halton DW, Walker B: Identification and characterization of the cysteine and serine proteinases of the trematode, Haplometra cylindracea and determination of their haemoglobinase activity. Parasitology. 1994 Jun;108 ( Pt 5):595-601. [PubMed:8052515 ]

    PMID: 9745358

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