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Arginyl-Leucine

July 24, 2017
Common Name

Arginyl-Leucine Description

Arginyl-Leucine is a dipeptide composed of arginine and leucine. 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-leuHMDB Arginine leucine dipeptideHMDB Arginine-leucine dipeptideHMDB ArginylleucineHMDB L-Arginyl-L-leucineHMDB R-L DipeptideHMDB RL DipeptideHMDB

Chemical Formlia

C12H25N5O3 Average Molecliar Weight

287.3586 Monoisotopic Molecliar Weight

287.195739691 IUPAC Name

2-(2-amino-5-carbamimidamidopentanamido)-4-methylpentanoic acid Traditional Name

2-(2-amino-5-carbamimidamidopentanamido)-4-methylpentanoic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C12H25N5O3/c1-7(2)6-9(11(19)20)17-10(18)8(13)4-3-5-16-12(14)15/h7-9H,3-6,13H2,1-2H3,(H,17,18)(H,19,20)(H4,14,15,16)

InChI Key

WYBVBIHNJWOLCJ-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

  • Leucine and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Methyl-branched fatty acids
  • N-acyl amines
  • Secondary carboxylic acid amides
  • Guanidines
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboxylic acids
  • Carboximidamides
  • Organopnictogen compounds
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organic oxides

    • Substituents

  • Alpha-dipeptide
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Guanidine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic 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-2.43Extrapolated

    Predicted Properties

    Property Value Source Water Solubility0.28 mg/mLALOGPS logP-3.2ALOGPS logP-2.4ChemAxon logS-3ALOGPS pKa (Strongest Acidic)3.84ChemAxon pKa (Strongest Basic)12.04ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area154.32 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity84.89 m3·mol-1ChemAxon Polarizability31.47 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-009i-2590000000-78c57f2abf5a6cfd8128View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-03fr-8930000000-b6bf7d2a5f3ee5d9a58fView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-03di-9100000000-8c5b699a045830f1654bView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-000f-1190000000-b8a73aa68c9e8ca98a48View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0a4l-5590000000-ef3340e524d0c61f6836View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-052f-9300000000-5d1b8c72765c9a2f5a21View in MoNA

    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

    HMDB28713 Metagene Link

    HMDB28713 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Acemetacin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Mironova NL, Pyshnyi DV, Ivanova EM, Zenkova MA, Gross HJ, Vlassov VV: Covalently attached oligodeoxyribonucleotides induce RNase activity of a short peptide and modulate its base specificity. Nucleic Acids Res. 2004 Mar 26;32(6):1928-36. Print 2004. [PubMed:15047859 ]
    2. 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 ]
    3. Morgan WT, Riehm JP: The isolation and some enzymatic properties of des-arginylleucine-lysozyme. Biochem Biophys Res Commun. 1968 Jan 11;30(1):50-6. [PubMed:5688915 ]

    PMID: 15026558

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