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Glutamyl-Glycine

July 21, 2017
Common Name

Glutamyl-Glycine Description

Glutamyl-Glycine is a dipeptide composed of glutamate and glycine. 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

MOLSDFPDBSMILESInChI

Structure for HMDB28819 (Glutamyl-Glycine)

Synonyms

Value Source e-g DipeptideHMDB EG dipeptideHMDB Glu-glyHMDB Glutamate glycine dipeptideHMDB Glutamate-glycine dipeptideHMDB GlutamylglycineHMDB L-Glutamyl-L-glycineHMDB

Chemical Formlia

C7H11N2O5 Average Molecliar Weight

203.1726 Monoisotopic Molecliar Weight

203.066796472 IUPAC Name

4-amino-4-[(carboxymethyl)carbamoyl]butanoate Traditional Name

4-amino-4-(carboxymethylcarbamoyl)butanoate CAS Registry Number

Not Available SMILES

NC(CCC([O-])=O)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C7H12N2O5/c8-4(1-2-5(10)11)7(14)9-3-6(12)13/h4H,1-3,8H2,(H,9,14)(H,10,11)(H,12,13)/p-1

InChI Key

LSPKYLAFTPBWIL-UHFFFAOYSA-M 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

  • Glutamic acid and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Amino fatty acids
  • N-acyl amines
  • Dicarboxylic acids and derivatives
  • Secondary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organic anions

    • Substituents

  • Alpha-dipeptide
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amino fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic anion
  • 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-4.61Extrapolated

    Predicted Properties

    Property Value Source Water Solubility76.0 mg/mLALOGPS logP-3.1ALOGPS logP-4.6ChemAxon logS-0.46ALOGPS pKa (Strongest Acidic)3.2ChemAxon pKa (Strongest Basic)8.45ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area132.55 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity54.93 m3·mol-1ChemAxon Polarizability18.6 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

    HMDB28819 Metagene Link

    HMDB28819 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Phytic acid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Christie JM, Jahr CE: Multivesicular release at Schaffer collateral-CA1 hippocampal synapses. J Neurosci. 2006 Jan 4;26(1):210-6. [PubMed:16399689 ]
    2. Chanda S, Xu-Friedman MA: A low-affinity antagonist reveals saturation and desensitization in mature synapses in the auditory brain stem. J Neurophysiol. 2010 Apr;103(4):1915-26. doi: 10.1152/jn.00751.2009. Epub 2010 Jan 27. [PubMed:20107122 ]
    3. Foster KA, Crowley JJ, Regehr WG: The influence of multivesicular release and postsynaptic receptor saturation on transmission at granule cell to Purkinje cell synapses. J Neurosci. 2005 Dec 14;25(50):11655-65. [PubMed:16354924 ]
    4. Normansell L, Panksepp J: Glutamatergic modulation of separation distress: profound emotional effects of excitatory amino acids in chicks. Neurosci Biobehav Rev. 2011 Oct;35(9):1890-901. doi: 10.1016/j.neubiorev.2011.06.004. Epub 2011 Jun 16. [PubMed:21704069 ]
    5. Wang Y, Ren C, Manis PB: Endbulb synaptic depression within the range of presynaptic spontaneous firing and its impact on the firing reliability of cochlear nucleus bushy neurons. Hear Res. 2010 Dec 1;270(1-2):101-9. doi: 10.1016/j.heares.2010.09.003. Epub 2010 Sep 17. [PubMed:20850512 ]
    6. Wu XS, Xue L, Mohan R, Paradiso K, Gillis KD, Wu LG: The origin of quantal size variation: vesicular glutamate concentration plays a significant role. J Neurosci. 2007 Mar 14;27(11):3046-56. [PubMed:17360928 ]
    7. Satake S, Song SY, Cao Q, Satoh H, Rusakov DA, Yanagawa Y, Ling EA, Imoto K, Konishi S: Characterization of AMPA receptors targeted by the climbing fiber transmitter mediating presynaptic inhibition of GABAergic transmission at cerebellar interneuron-Purkinje cell synapses. J Neurosci. 2006 Feb 22;26(8):2278-89. [PubMed:16495455 ]
    8. Beurrier C, Faideau M, Bennouar KE, Escartin C, Kerkerian-Le Goff L, Bonvento G, Gubellini P: Ciliary neurotrophic factor protects striatal neurons against excitotoxicity by enhancing glial glutamate uptake. PLoS One. 2010 Jan 1;5(1):e8550. doi: 10.1371/journal.pone.0008550. [PubMed:20062544 ]
    9. Bowser TE, Trawick ML: Probing the specificity of gamma-glutamylamine cyclotransferase: an enzyme involved in the metabolism of transglutaminase-catalyzed protein crosslinks. Amino Acids. 2013 Jan;44(1):143-50. doi: 10.1007/s00726-011-1153-2. Epub 2011 Nov 27. [PubMed:22120669 ]
    10. Sun YG, Beierlein M: Receptor saturation controls short-term synaptic plasticity at corticothalamic synapses. J Neurophysiol. 2011 May;105(5):2319-29. doi: 10.1152/jn.00942.2010. Epub 2011 Feb 16. [PubMed:21325678 ]
    11. Renden R, Taschenberger H, Puente N, Rusakov DA, Duvoisin R, Wang LY, Lehre KP, von Gersdorff H: Glutamate transporter studies reveal the pruning of metabotropic glutamate receptors and absence of AMPA receptor desensitization at mature calyx of Held synapses. J Neurosci. 2005 Sep 14;25(37):8482-97. [PubMed:16162930 ]

    PMID: 6223827

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