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Glycyl-Histidine

July 21, 2017
Common Name

Glycyl-Histidine Description

Glycyl-Histidine is a dipeptide composed of glycine 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB28843 (Glycyl-Histidine)

Synonyms

Value Source g-H DipeptideHMDB GH DipeptideHMDB Gly-hisHMDB Glycine histidine dipeptideHMDB Glycine-histidine dipeptideHMDB GlycylhistidineHMDB L-Glycyl-L-histidineHMDB Glycyl-L-histidineMeSH Glycylhistidine, monohydrochlorideMeSH

Chemical Formlia

C8H12N4O3 Average Molecliar Weight

212.2059 Monoisotopic Molecliar Weight

212.09094027 IUPAC Name

2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanoic acid Traditional Name

2-(2-aminoacetamido)-3-(3H-imidazol-4-yl)propanoic acid CAS Registry Number

Not Available SMILES

NCC(=O)NC(CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C8H12N4O3/c9-2-7(13)12-6(8(14)15)1-5-3-10-4-11-5/h3-4,6H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15)

InChI Key

YIWFXZNIBQBFHR-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

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

    • Substituents

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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Detected 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-4.49Extrapolated

    Predicted Properties

    Property Value Source Water Solubility11.7 mg/mLALOGPS logP-3ALOGPS logP-4.6ChemAxon logS-1.3ALOGPS pKa (Strongest Acidic)3.27ChemAxon pKa (Strongest Basic)8.16ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area121.1 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity50.86 m3·mol-1ChemAxon Polarizability20.17 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

  • Sweat

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF

  • Adriana Nori…

    • details

    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

    HMDB28843 Metagene Link

    HMDB28843 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: 11beta-Hydroxyprogesterone

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
    2. Girelli AM, Mattei E, Messina A, Tarola AM: Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem. 2004 May 19;52(10):2741-5. [PubMed:15137808 ]
    3. Islam MK, Tsuboya C, Kusaka H, Aizawa S, Ueki T, Michibata H, Kanamori K: Reduction of vanadium(V) to vanadium(IV) by NADPH, and vanadium(IV) to vanadium(III) by cysteine methyl ester in the presence of biologically relevant ligands. Biochim Biophys Acta. 2007 Aug;1770(8):1212-8. Epub 2007 May 21. [PubMed:17574763 ]
    4. Turecek F, Yao C, Fung YM, Hayakawa S, Hashimoto M, Matsubara H: Histidine-containing radicals in the gas phase. J Phys Chem B. 2009 May 21;113(20):7347-66. doi: 10.1021/jp900719n. [PubMed:19388698 ]
    5. Inoue S, Kawanishi S: ESR evidence for superoxide, hydroxyl radicals and singlet oxygen produced from hydrogen peroxide and nickel(II) complex of glycylglycyl-L-histidine. Biochem Biophys Res Commun. 1989 Mar 15;159(2):445-51. [PubMed:2539111 ]
    6. Kapota C, Ohanessian G: The low energy tautomers and conformers of the dipeptides HisGly and GlyHis and of their sodium ion complexes in the gas phase. Phys Chem Chem Phys. 2005 Nov 7;7(21):3744-55. Epub 2005 Sep 9. [PubMed:16358024 ]
    7. Casella G, Ferrante F, Saielli G: DFT calculation of 1J(119Sn,13C) and 2J(119Sn,1H) coupling constants in di- and trimethyltin(IV) compounds. Inorg Chem. 2008 Jun 2;47(11):4796-807. doi: 10.1021/ic8000976. Epub 2008 May 6. [PubMed:18459719 ]
    8. Zhang J, Yu X, Zeng B, Cai S, Chen Z: Spectroscopic and theoretical study on the interaction between diperoxovanadate complexes and glycyl-histidine. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Nov;77(4):825-31. doi: 10.1016/j.saa.2010.08.013. Epub 2010 Aug 11. [PubMed:20822949 ]

    PMID: 21976495

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