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Glycyl-Arginine

July 21, 2017
Common Name

Glycyl-Arginine Description

Glycyl-Arginine is a dipeptide composed of glycine 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 HMDB28835 (Glycyl-Arginine)

Synonyms

Value Source g-R DipeptideHMDB Gly-argHMDB Glycine arginine dipeptideHMDB Glycine-arginine dipeptideHMDB GlycylarginineHMDB GR DipeptideHMDB L-Glycyl-L-arginineHMDB

Chemical Formlia

C8H17N5O3 Average Molecliar Weight

231.2523 Monoisotopic Molecliar Weight

231.133139435 IUPAC Name

2-(2-aminoacetamido)-5-carbamimidamidopentanoic acid Traditional Name

2-(2-aminoacetamido)-5-carbamimidamidopentanoic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C8H17N5O3/c9-4-6(14)13-5(7(15)16)2-1-3-12-8(10)11/h5H,1-4,9H2,(H,13,14)(H,15,16)(H4,10,11,12)

InChI Key

JLXVRFDTDUGQEE-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

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

    • Substituents

  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Guanidine
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen 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-4.25Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.01 mg/mLALOGPS logP-3.8ALOGPS logP-4.2ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)3.6ChemAxon pKa (Strongest Basic)12.18ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area154.32 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity66.73 m3·mol-1ChemAxon Polarizability23.4 Å3ChemAxon Number of Rings0ChemAxon 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

    HMDB28835 Metagene Link

    HMDB28835 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Vanilpyruvic acid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Prell JS, Demireva M, Oomens J, Williams ER: Role of sequence in salt-bridge formation for alkali metal cationized GlyArg and ArgGly investigated with IRMPD spectroscopy and theory. J Am Chem Soc. 2009 Jan 28;131(3):1232-42. doi: 10.1021/ja808177z. [PubMed:19117387 ]
    2. Wallace RJ, McKain N, Broderick GA, Rode LM, Walker ND, Newbold CJ, Kopecny J: Peptidases of the rumen bacterium, Prevotella ruminicola. Anaerobe. 1997 Feb;3(1):35-42. [PubMed:16887560 ]
    3. Lacourse KA, Friis-Hansen L, Samuelson LC, Rehfeld JF: Altered processing of procholecystokinin in carboxypeptidase E-deficient fat mice: differential synthesis in neurons and endocrine cells. FEBS Lett. 1998 Sep 25;436(1):61-6. [PubMed:9771894 ]
    4. Wallace RJ, McKain N: A survey of peptidase activity in rumen bacteria. J Gen Microbiol. 1991 Sep;137(9):2259-64. [PubMed:1748877 ]
    5. Bleakman A, Smyth DG: Sequential processing reactions in the formation of hormone amides. Eur J Biochem. 1987 Aug 17;167(1):161-5. [PubMed:3113947 ]
    6. Roche PC, Ryan RJ: Electrophoretic analysis of membrane proteases in the luteinized rat ovary. Endocrinology. 1986 Aug;119(2):495-501. [PubMed:3525119 ]
    7. McKain N, Wallace RJ, Watt ND: Selective isolation of bacteria with dipeptidyl aminopeptidase type I activity from the sheep rumen. FEMS Microbiol Lett. 1992 Aug 15;74(2-3):169-73. [PubMed:1526449 ]
    8. Ishiura S, Anraku H, Kamo I, Koizumi H, Arahata K, Sugita H: Isolation of a Ca-dependent erythrolytic protein (perforin) from cytotoxic T-lymphocytes. J Biochem. 1987 Jul;102(1):9-12. [PubMed:3499435 ]

    PMID: 19649285

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