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Histidinyl-Glycine

July 21, 2017
Common Name

Histidinyl-Glycine Description

Histidinyl-Glycine is a dipeptide composed of histidine 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 HMDB28885 (Histidinyl-Glycine)

Synonyms

Value Source H-g DipeptideHMDB HG DipeptideHMDB His-glyHMDB Histidine glycine dipeptideHMDB Histidine-glycine dipeptideHMDB HistidinylglycineHMDB L-Histidinyl-L-glycineHMDB HistidylglycineMeSH

Chemical Formlia

C8H12N4O3 Average Molecliar Weight

212.2059 Monoisotopic Molecliar Weight

212.09094027 IUPAC Name

2-[2-amino-3-(1H-imidazol-5-yl)propanamido]acetic acid Traditional Name

[2-amino-3-(3H-imidazol-4-yl)propanamido]acetic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C8H12N4O3/c9-6(1-5-2-10-4-12-5)8(15)11-3-7(13)14/h2,4,6H,1,3,9H2,(H,10,12)(H,11,15)(H,13,14)

InChI Key

LYCVKHSJGDMDLM-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
  • Aralkylamines
  • Fatty amides
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Azacyclic compounds
  • Carboxylic acids
  • Carbonyl compounds
  • Organic oxides
  • Organopnictogen compounds
  • Monoalkylamines
  • Hydrocarbon derivatives

    • Substituents

  • Alpha-dipeptide
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Fatty acyl
  • Fatty amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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-4.58Extrapolated

    Predicted Properties

    Property Value Source Water Solubility8.58 mg/mLALOGPS logP-2.9ALOGPS logP-4.5ChemAxon logS-1.4ALOGPS pKa (Strongest Acidic)3.34ChemAxon pKa (Strongest Basic)8.02ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area121.1 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity50.86 m3·mol-1ChemAxon Polarizability20.42 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

    HMDB28885 Metagene Link

    HMDB28885 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: 1,3-Dicaffeoylquinic acid

    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. 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 ]
    3. Wickrama Arachchilage AP, Wang F, Feyer V, Plekan O, Prince KC: Photoelectron spectra and structures of three cyclic dipeptides: PhePhe, TyrPro, and HisGly. J Chem Phys. 2012 Mar 28;136(12):124301. doi: 10.1063/1.3693763. [PubMed:22462851 ]
    4. Tesfai TM, Green BJ, Margerum DW: Decomposition kinetics of Ni(III)-peptide complexes with histidine and histamine as the third residue. Inorg Chem. 2004 Oct 18;43(21):6726-33. [PubMed:15476372 ]
    5. Hanaki A, Odani A: Transport of Cu(II) from an albumin mimic peptide, GlyGlyHisGly, to histidine and penicillamine. J Inorg Biochem. 2007 Oct;101(10):1428-37. Epub 2007 Jun 12. [PubMed:17643491 ]
    6. Burke SK, Xu Y, Margerum DW: Cu(II)Gly2HisGly oxidation by H2O2/ascorbic acid to the CuIII complex and its subsequent decay to alkene peptides. Inorg Chem. 2003 Sep 22;42(19):5807-17. [PubMed:12971748 ]
    7. Green BJ, Tesfai TM, Margerum DW: Nickel(III) oxidation of its glycylglycylhistamine complex. Dalton Trans. 2004 Nov 7;(21):3508-14. Epub 2004 Sep 20. [PubMed:15510270 ]

    PMID: 9630361

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