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Glycyl-Tryptophan

July 21, 2017
Common Name

Glycyl-Tryptophan Description

Glycyl-Tryptophan is a dipeptide composed of glycine and tryptophan. 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 HMDB28852 (Glycyl-Tryptophan)

Synonyms

Value Source g-W DipeptideHMDB Gly-TRPHMDB Glycine tryptophan dipeptideHMDB Glycine-tryptophan dipeptideHMDB GlycyltryptophanHMDB GW DipeptideHMDB L-Glycyl-L-tryptophanHMDB Glycyl-L-tryptophanMeSH Glycyltryptophan, (DL)-isomerMeSH

Chemical Formlia

C13H15N3O3 Average Molecliar Weight

261.2765 Monoisotopic Molecliar Weight

261.111341361 IUPAC Name

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

2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanoic acid CAS Registry Number

Not Available SMILES

NCC(=O)NC(CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C13H15N3O3/c14-6-12(17)16-11(13(18)19)5-8-7-15-10-4-2-1-3-9(8)10/h1-4,7,11,15H,5-6,14H2,(H,16,17)(H,18,19)

InChI Key

AJHCSUXXECOXOY-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

  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Indolyl carboxylic acids and derivatives
  • 3-alkylindoles
  • Substituted pyrroles
  • Benzenoids
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Azacyclic compounds
  • Monocarboxylic acids and derivatives
  • Monoalkylamines
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organic oxides

    • Substituents

  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic 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-2.19Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.19 mg/mLALOGPS logP-1.2ALOGPS logP-2.2ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)3.82ChemAxon pKa (Strongest Basic)8.14ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area108.21 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity69.01 m3·mol-1ChemAxon Polarizability26.57 Å3ChemAxon Number of Rings2ChemAxon 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

    HMDB28852 Metagene Link

    HMDB28852 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: TPPU

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Kano K, Hasegawa H, Miyamura M: Chiral recognition of dipeptide methyl esters by an anionic beta-cyclodextrin. Chirality. 2001 Aug;13(8):474-82. [PubMed:11466771 ]
    2. Jean PA, Reed DJ: In vitro dipeptide, nucleoside, and glutathione alkylation by S-(2-chloroethyl)glutathione and S-(2-chloroethyl)-L-cysteine. Chem Res Toxicol. 1989 Nov-Dec;2(6):455-60. [PubMed:2519737 ]
    3. Lozovskaia EL, Makareeva EN, Makedonov IU: [Photosensitization and photoprotection by some drugs, metabolites and other compounds]. Biofizika. 1997 May-Jun;42(3):549-57. [PubMed:9296615 ]
    4. Eisenberg AS, Juszczak LJ: Correlation of TrpGly and GlyTrp Rotamer Structure with W7 and W10 UV Resonance Raman Modes and Fluorescence Emission Shifts. J Amino Acids. 2012;2012:735076. doi: 10.1155/2012/735076. Epub 2012 Jul 22. [PubMed:22888404 ]
    5. Babizhayev MA, Lozovskaya EL, Makareyeva EN, Lulkin YA, Sapezhinskii II: Photoprotector and antioxidant properties of histamine-containing peptidomimetics in the photooxidation of glycyltryptophan. Biochemistry (Mosc). 1998 May;63(5):523-8. [PubMed:9632886 ]
    6. Lozovskaia EL, Sapezhinskii II: [Comparative effectiveness of some medicinal substances as acceptors of superoxide radicals]. Biofizika. 1993 Jan-Feb;38(1):31-6. [PubMed:8386002 ]
    7. Viell B, Weidler B, Krause B, Vestweber KH: Analysis of tryptophan, tyrosine and related dipeptides in mouse brain by isocratic high-performance liquid chromatography with switchable wavelength fluorescence detection. J Pharm Biomed Anal. 1988;6(6-8):933-8. [PubMed:16867364 ]
    8. Turoverov KK, Kuznetsova IM: What causes the depolarization of trypsin and trypsinogen fluorescence. Intramolecular mobility or non-radiative energy transfer? Biophys Chem. 1986 Dec 31;25(3):315-23. [PubMed:3828470 ]
    9. Lozovskaia EL, Kaplunskii GD, Sapezhinskii II: [Superoxide dismutase activity and photosensitizing properties of 2,5-dihydroxybenzolsulfonate]. Biofizika. 1990 Nov-Dec;35(6):912-6. [PubMed:1965686 ]
    10. Norberg A, Sillard R, Carlquist M, Jornvall H, Mutt V: Chemical detection of natural peptides by specific structures. Isolation of chicken galanin by monitoring for its N-terminal dipeptide, and determination of the amino acid sequence. FEBS Lett. 1991 Aug 19;288(1-2):151-3. [PubMed:1715289 ]
    11. Drozdz R, Naskalski JW, Sznajd J: Oxidation of amino acids and peptides in reaction with myeloperoxidase, chloride and hydrogen peroxide. Biochim Biophys Acta. 1988 Nov 2;957(1):47-52. [PubMed:2846070 ]
    12. Lozovskaya EL, Vartanyan LS: Superoxide dismutase: determination of activity by inhibition of photosensitized chemiluminescence of glycyltryptophan. Biochemistry (Mosc). 2000 May;65(5):599-603. [PubMed:10851038 ]
    13. Kaplunskii GD, Sapezhinskii II: [Protection and latent and patent sensitization by nucleotides of radiation-induced transformations of gylcyltryptophan and serum albumin]. Radiobiologiia. 1988 Jul-Aug;28(4):549-53. [PubMed:3420231 ]
    14. Popova TV, Reinbolt J, Ehresmann B, Shakirov MM, Serebriakova MV, Gerassimova YV, Knorre DG, Godovikova TS: Why do p-nitro-substituted aryl azides provide unintended dark reactions with proteins? J Photochem Photobiol B. 2010 Jul 2;100(1):19-29. doi: 10.1016/j.jphotobiol.2010.04.004. Epub 2010 Apr 14. [PubMed:20570168 ]

    PMID: 10837852

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