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Arginyl-Phenylalanine

July 24, 2017
Common Name

Arginyl-Phenylalanine Description

Arginyl-Phenylalanine is a dipeptide composed of arginine and phenylalanine. 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

Synonyms

Value Source Arg-pheHMDB Arginine phenylalanine dipeptideHMDB Arginine-phenylalanine dipeptideHMDB ArginylphenylalanineHMDB L-Arginyl-L-phenylalanineHMDB R-F DipeptideHMDB RF DipeptideHMDB

Chemical Formlia

C15H23N5O3 Average Molecliar Weight

321.3748 Monoisotopic Molecliar Weight

321.180089627 IUPAC Name

2-(2-amino-5-carbamimidamidopentanamido)-3-phenylpropanoic acid Traditional Name

2-(2-amino-5-carbamimidamidopentanamido)-3-phenylpropanoic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

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

InChI Key

PQBHGSGQZSOLIR-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
  • Phenylpropanoic acids
  • Amphetamines and derivatives
  • N-acyl amines
  • Secondary carboxylic acid amides
  • Amino acids
  • Guanidines
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboximidamides
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Organopnictogen compounds
  • Organic oxides
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Benzenoid
  • Fatty amide
  • Fatty acyl
  • Guanidine
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Organic 1,3-dipolar compound
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility0.16 mg/mLALOGPS logP-3.1ALOGPS logP-2ChemAxon logS-3.3ALOGPS pKa (Strongest Acidic)3.71ChemAxon pKa (Strongest Basic)12.04ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area154.32 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity95.84 m3·mol-1ChemAxon Polarizability33.82 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

    HMDB28716 Metagene Link

    HMDB28716 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Thiamphenicol

    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. Dockray GJ, Reeve JR Jr, Shively J, Gayton RJ, Barnard CS: A novel active pentapeptide from chicken brain identified by antibodies to FMRFamide. Nature. 1983 Sep 22-28;305(5932):328-30. [PubMed:6137771 ]

    PMID: 18644798

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