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Glutaminyl-Glycine

July 21, 2017
Common Name

Glutaminyl-Glycine Description

Glutaminyl-Glycine is a dipeptide composed of glutamine 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB28797 (Glutaminyl-Glycine)

Synonyms

Value Source GLN-GlyHMDB Glutamine glycine dipeptideHMDB Glutamine-glycine dipeptideHMDB GlutaminylglycineHMDB L-Glutaminyl-L-glycineHMDB Q-g DipeptideHMDB QG DipeptideHMDB

Chemical Formlia

C7H13N3O4 Average Molecliar Weight

203.1958 Monoisotopic Molecliar Weight

203.090605919 IUPAC Name

2-(2-amino-4-carbamoylbutanamido)acetic acid Traditional Name

(2-amino-4-carbamoylbutanamido)acetic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C7H13N3O4/c8-4(1-2-5(9)11)7(14)10-3-6(12)13/h4H,1-3,8H2,(H2,9,11)(H,10,14)(H,12,13)

InChI Key

JEFZIKRIDLHOIF-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

  • Glutamine and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • N-acyl amines
  • Secondary carboxylic acid amides
  • Primary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Alpha-dipeptide
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • 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-5.11Extrapolated

    Predicted Properties

    Property Value Source Water Solubility15.5 mg/mLALOGPS logP-3.3ALOGPS logP-5.1ChemAxon logS-1.1ALOGPS pKa (Strongest Acidic)3.53ChemAxon pKa (Strongest Basic)8.23ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area135.51 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity45.91 m3·mol-1ChemAxon Polarizability19.41 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

    HMDB28797 Metagene Link

    HMDB28797 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Cenerimod

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Kee AJ, Smith RC, Gross AS, Madsen DC, Rowe B: The effect of dipeptide structure on dipeptide and amino acid clearance in rats. Metabolism. 1994 Nov;43(11):1373-8. [PubMed:7968592 ]
    2. Kitaoka M, Tsuruda Y, Tanaka Y, Goto M, Mitsumori M, Hayashi K, Hiraishi Y, Miyawaki K, Noji S, Kamiya N: Transglutaminase-mediated synthesis of a DNA-(enzyme)n probe for highly sensitive DNA detection. Chemistry. 2011 May 2;17(19):5387-92. doi: 10.1002/chem.201003744. Epub 2011 Apr 5. [PubMed:21469233 ]
    3. Abe T, Chung SI, DiAugustine RP, Folk JE: Rabbit liver transglutaminase: physical, chemical, and catalytic properties. Biochemistry. 1977 Dec 13;16(25):5495-501. [PubMed:21685 ]
    4. Inoue M, Morino Y: Inactivation of renal gamma-glutamyl transferase by 6-diazo-5-oxo-L-norleucylglycine, an inactive precursor of affinity-labeling reagent. Proc Natl Acad Sci U S A. 1981 Jan;78(1):46-9. [PubMed:6113588 ]
    5. Kamiya N, Abe H, Goto M, Tsuji Y, Jikuya H: Fluorescent substrates for covalent protein labeling catalyzed by microbial transglutaminase. Org Biomol Chem. 2009 Sep 7;7(17):3407-12. doi: 10.1039/b904046c. Epub 2009 Jun 30. [PubMed:19675894 ]
    6. Yang MT, Chang CH, Wang JM, Wu TK, Wang YK, Chang CY, Li TT: Crystal structure and inhibition studies of transglutaminase from Streptomyces mobaraense. J Biol Chem. 2011 Mar 4;286(9):7301-7. doi: 10.1074/jbc.M110.203315. Epub 2010 Dec 29. [PubMed:21193394 ]
    7. Pasternack R, Laurent HP, Ruth T, Kaiser A, Schon N, Fuchsbauer HL: A fluorescent substrate of transglutaminase for detection and characterization of glutamine acceptor compounds. Anal Biochem. 1997 Jun 15;249(1):54-60. [PubMed:9193708 ]
    8. Suchanek G, Kreil G: Translation of melittin messenger RNA in vitro yields a product terminating with glutaminylglycine rather than with glutaminamide. Proc Natl Acad Sci U S A. 1977 Mar;74(3):975-8. [PubMed:265590 ]
    9. Kamiya N, Abe H: New fluorescent substrates of microbial transglutaminase and its application to peptide tag-directed covalent protein labeling. Methods Mol Biol. 2011;751:81-94. doi: 10.1007/978-1-61779-151-2_7. [PubMed:21674327 ]
    10. Fink ML, Shao YY, Kersh GJ: A fluorometric, high-performance liquid chromatographic assay for transglutaminase activity. Anal Biochem. 1992 Mar;201(2):270-6. [PubMed:1352948 ]
    11. Leyton P, Saladino R, Crestini C, Campos-Vallette M, Paipa C, Berrios A, Fuentes S, Zarate RA: Influence of TiO2 on prebiotic thermal synthesis of the Gly-Gln polymer. Amino Acids. 2012 Jun;42(6):2079-88. doi: 10.1007/s00726-011-0939-6. Epub 2011 May 24. [PubMed:21607746 ]

    PMID: 9422797

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