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Glutamyl-Histidine

July 21, 2017
Common Name

Glutamyl-Histidine Description

Glutamyl-Histidine is a dipeptide composed of glutamate and histidine. 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 HMDB28821 (Glutamyl-Histidine)

Synonyms

Value Source e-H DipeptideHMDB EH dipeptideHMDB Glu-hisHMDB Glutamate histidine dipeptideHMDB Glutamate-histidine dipeptideHMDB GlutamylhistidineHMDB L-Glutamyl-L-histidineHMDB

Chemical Formlia

C11H15N4O5 Average Molecliar Weight

283.2606 Monoisotopic Molecliar Weight

283.10424461 IUPAC Name

4-amino-4-{[1-carboxy-2-(1H-imidazol-5-yl)ethyl]carbamoyl}butanoate Traditional Name

4-amino-4-{[1-carboxy-2-(3H-imidazol-4-yl)ethyl]carbamoyl}butanoate CAS Registry Number

Not Available SMILES

NC(CCC([O-])=O)C(=O)NC(CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H16N4O5/c12-7(1-2-9(16)17)10(18)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,18)(H,16,17)(H,19,20)/p-1

InChI Key

HKTRDWYCAUTRRL-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

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

    • Substituents

  • Alpha-dipeptide
  • Histidine or derivatives
  • 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
  • Imidazolyl carboxylic acid derivative
  • Amino fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic anion
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic 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-6.19Extrapolated

    Predicted Properties

    Property Value Source Water Solubility13.3 mg/mLALOGPS logP-3.1ALOGPS logP-6.3ChemAxon logS-1.4ALOGPS pKa (Strongest Acidic)3.05ChemAxon pKa (Strongest Basic)8.46ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area161.23 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity76.98 m3·mol-1ChemAxon Polarizability26.82 Å3ChemAxon Number of Rings1ChemAxon 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

    HMDB28821 Metagene Link

    HMDB28821 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: CC0651

    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. Sovago I, Farkas E, Bertalan C, Lebkiri A, Kowalik-Jankowska T, Kozlowski H: Copper(II) complexes of dipeptides containing aspartyl, glutamyl, and histidyl residues in the side chain. J Inorg Biochem. 1993 Sep;51(4):715-26. [PubMed:7902418 ]
    3. Kakimoto Y, Konishi H: Occurrence of gamma-glutamylhistidine in bovine brain. J Neurochem. 1976 Jun;26(6):1263-5. [PubMed:932730 ]

    PMID: 25642174

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