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Glutamyl-Glutamate

July 21, 2017
Common Name

Glutamyl-Glutamate Description

Glutamyl-Glutamate is a dipeptied compoosed of two glutamate residues. 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 HMDB28818 (Glutamyl-Glutamate)

Synonyms

Value Source e-e DipeptideHMDB EE dipeptideHMDB Glu-gluHMDB Glutamate glutamate dipeptideHMDB Glutamate-glutamate dipeptideHMDB GlutamylglutamateHMDB L-Glutamyl-L-glutamateHMDB

Chemical Formlia

C10H14N2O7 Average Molecliar Weight

274.2274 Monoisotopic Molecliar Weight

274.080100812 IUPAC Name

4-amino-4-[(3-carboxy-1-carboxylatopropyl)carbamoyl]butanoate Traditional Name

4-amino-4-[(3-carboxy-1-carboxylatopropyl)carbamoyl]butanoate CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C10H16N2O7/c11-5(1-3-7(13)14)9(17)12-6(10(18)19)2-4-8(15)16/h5-6H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/p-2

InChI Key

KOSRFJWDECSPRO-UHFFFAOYSA-L 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
  • Tricarboxylic acids and derivatives
  • Amino fatty acids
  • N-acyl amines
  • 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
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • 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-4.37Extrapolated

    Predicted Properties

    Property Value Source Water Solubility68.7 mg/mLALOGPS logP-3ALOGPS logP-4.4ChemAxon logS-0.65ALOGPS pKa (Strongest Acidic)3.06ChemAxon pKa (Strongest Basic)8.45ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area172.68 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity81.05 m3·mol-1ChemAxon Polarizability25 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

    HMDB28818 Metagene Link

    HMDB28818 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: [6]-Gingerol

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Sandberg M, Li X, Folestad S, Weber SG, Orwar O: Liquid chromatographic determination of acidic beta-aspartyl and gamma-glutamyl peptides in extracts of rat brain. Anal Biochem. 1994 Feb 15;217(1):48-61. [PubMed:7911284 ]
    2. Tamemoto H, Ishikawa SE, Kawakami M: Association of the Glu298Asp polymorphism of the eNOS Gene with ischemic heart disease in Japanese diabetic subjects. Diabetes Res Clin Pract. 2008 May;80(2):275-9. doi: 10.1016/j.diabres.2007.12.019. Epub 2008 Feb 19. [PubMed:18243394 ]
    3. Takahashi N, Sato T, Yamada T: Metabolic pathways for cytotoxic end product formation from glutamate- and aspartate-containing peptides by Porphyromonas gingivalis. J Bacteriol. 2000 Sep;182(17):4704-10. [PubMed:10940008 ]
    4. Takahashi N, Sato T: Preferential utilization of dipeptides by Porphyromonas gingivalis. J Dent Res. 2001 May;80(5):1425-9. [PubMed:11437213 ]
    5. Takahashi N, Sato T: Dipeptide utilization by the periodontal pathogens Porphyromonas gingivalis, Prevotella intermedia, Prevotella nigrescens and Fusobacterium nucleatum. Oral Microbiol Immunol. 2002 Feb;17(1):50-4. [PubMed:11860556 ]
    6. Varga V, Janaky R, Saransaari P, Oja SS: Endogenous gamma-L-glutamyl and beta-L-aspartyl peptides and excitatory aminoacidergic neurotransmission in the brain. Neuropeptides. 1994 Jul;27(1):19-26. [PubMed:7969817 ]
    7. Li X, Orwar O, Revesjo C, Sandberg M: Gamma-glutamyl peptides and related amino acids in rat hippocampus in vitro: effect of depolarization and gamma-glutamyl transpeptidase inhibition. Neurochem Int. 1996 Aug;29(2):121-8. [PubMed:8837040 ]
    8. Orwar O, Li X, Andine P, Bergstrom CM, Hagberg H, Folestad S, Sandberg M: Increased intra- and extracellular concentrations of gamma-glutamylglutamate and related dipeptides in the ischemic rat striatum: involvement of glutamyl transpeptidase. J Neurochem. 1994 Oct;63(4):1371-6. [PubMed:7931288 ]
    9. Neelakantan S, Surjawan I, Karacelik H, Hicks CL, Crooks PA: Synthesis of novel isoluminol probes and their use in rapid bacterial assays. Bioorg Med Chem Lett. 2009 Oct 1;19(19):5722-6. doi: 10.1016/j.bmcl.2009.08.004. Epub 2009 Aug 6. [PubMed:19700327 ]
    10. Kannan R, Kuhlenkamp JF, Ookhtens M, Kaplowitz N: Transport of glutathione at blood-brain barrier of the rat: inhibition by glutathione analogs and age-dependence. J Pharmacol Exp Ther. 1992 Dec;263(3):964-70. [PubMed:1469653 ]
    11. Hagen TM, Jones DP: Transepithelial transport of glutathione in vascularly perfused small intestine of rat. Am J Physiol. 1987 May;252(5 Pt 1):G607-13. [PubMed:3578519 ]
    12. McKernan TB, Woods EB, Lash LH: Uptake of glutathione by renal cortical mitochondria. Arch Biochem Biophys. 1991 Aug 1;288(2):653-63. [PubMed:1680311 ]
    13. Varga V, Janaky R, Holopainen I, Oja SS, Akerman KE: Endogenous gamma-L-glutamylglutamate is a partial agonist at the N-methyl-D-aspartate receptors in cultured cerebellar granule cells. Neurochem Res. 1995 Dec;20(12):1471-6. [PubMed:8789610 ]
    14. Tsukamoto T, Flanary JM, Rojas C, Slusher BS, Valiaeva N, Coward JK: Phosphonate and phosphinate analogues of N-acylated gamma-glutamylglutamate. potent inhibitors of glutamate carboxypeptidase II. Bioorg Med Chem Lett. 2002 Aug 19;12(16):2189-92. [PubMed:12127534 ]
    15. Kannan R, Kuhlenkamp JF, Jeandidier E, Trinh H, Ookhtens M, Kaplowitz N: Evidence for carrier-mediated transport of glutathione across the blood-brain barrier in the rat. J Clin Invest. 1990 Jun;85(6):2009-13. [PubMed:1971830 ]
    16. Hagen TM, Aw TY, Jones DP: Glutathione uptake and protection against oxidative injury in isolated kidney cells. Kidney Int. 1988 Jul;34(1):74-81. [PubMed:3172638 ]
    17. Guo H, Yang J, Gallazzi F, Prossnitz ER, Sklar LA, Miao Y: Effect of DOTA position on melanoma targeting and pharmacokinetic properties of 111In-labeled lactam bridge-cyclized alpha-melanocyte stimulating hormone peptide. Bioconjug Chem. 2009 Nov;20(11):2162-8. doi: 10.1021/bc9003475. [PubMed:19817405 ]

    PMID: 7897596

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