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Phenylalanyl-Glycine

July 21, 2017
Common Name

Phenylalanyl-Glycine Description

Phenylalanyl-Glycine is a dipeptide composed of phenylalanine 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 HMDB28995 (Phenylalanyl-Glycine)

Synonyms

Value Source F-g DipeptideHMDB FG DipeptideHMDB L-Phenylalanyl-L-glycineHMDB Phe-glyHMDB Phenylalanine glycine dipeptideHMDB Phenylalanine-glycine dipeptideHMDB PhenylalanylglycineHMDB L-PhenylalanylglycineMeSH

Chemical Formlia

C11H14N2O3 Average Molecliar Weight

222.2405 Monoisotopic Molecliar Weight

222.100442324 IUPAC Name

2-(2-amino-3-phenylpropanamido)acetic acid Traditional Name

(2-amino-3-phenylpropanamido)acetic acid CAS Registry Number

Not Available SMILES

NC(CC1=CC=CC=C1)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)

InChI Key

GLUBLISJVJFHQS-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

  • Phenylalanine and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Amphetamines and derivatives
  • Aralkylamines
  • Fatty amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Aralkylamine
  • Fatty amide
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic 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-2.29Extrapolated

    Predicted Properties

    Property Value Source Water Solubility0.78 mg/mLALOGPS logP-0.9ALOGPS logP-2.3ChemAxon logS-2.5ALOGPS pKa (Strongest Acidic)3.71ChemAxon pKa (Strongest Basic)8.01ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity57.92 m3·mol-1ChemAxon Polarizability22.83 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

    HMDB28995 Metagene Link

    HMDB28995 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Puerarin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Pingitore F, Wesdemiotis C: Characterization of dipeptide isomers by tandem mass spectrometry of their mono- versus dilithiated complexes. Anal Chem. 2005 Mar 15;77(6):1796-806. [PubMed:15762588 ]
    2. Thirumoorthy K, Soni K, Nandi N: The molecular recognition of dipeptide by oligoglycyl head group of amphiphile: a quantum chemical study. J Nanosci Nanotechnol. 2009 Jan;9(1):77-89. [PubMed:19441281 ]
    3. Epand RM: Virus replication inhibitory peptide inhibits the conversion of phospholipid bilayers to the hexagonal phase. Biosci Rep. 1986 Jul;6(7):647-53. [PubMed:3779040 ]
    4. Storer AC, Angus RH, Carey PR: Comparison of the kinetics of the papain-catalyzed hydrolysis of glycine- and alanine-based esters and thiono esters. Biochemistry. 1988 Jan 12;27(1):264-8. [PubMed:3349032 ]
    5. Li L, Zheng LX, Yang FY: Effect of propensity of hexagonal II phase formation on the activity of mitochondrial ubiquinol-cytochrome c reductase and H(+)-ATPase. Chem Phys Lipids. 1995 Jun 19;76(2):135-44. [PubMed:7634362 ]
    6. Ningsih F, Kitani S, Fukushima E, Nihira T: VisG is essential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine. Microbiology. 2011 Nov;157(Pt 11):3213-20. doi: 10.1099/mic.0.050203-0. Epub 2011 Aug 4. [PubMed:21816878 ]
    7. Kruger RG, Lu W, Oberthur M, Tao J, Kahne D, Walsh CT: Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operons. Chem Biol. 2005 Jan;12(1):131-40. [PubMed:15664522 ]
    8. Makowski M, Lisowski M, Maciag A, Wiktor M, Szlachcic A, Lis T: Two pentadehydropeptides with different configurations of the DeltaPhe residues. Acta Crystallogr C. 2010 Mar;66(Pt 3):o119-23. doi: 10.1107/S0108270110003094. Epub 2010 Feb 3. [PubMed:20203407 ]
    9. Fujita T, Morishita Y, Ito H, Kuribayashi D, Yamamoto A, Muranishi S: Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids. Life Sci. 1997;61(25):2455-65. [PubMed:9416764 ]
    10. Yeagle PL, Young J, Hui SW, Epand RM: On the mechanism of inhibition of viral and vesicle membrane fusion by carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine. Biochemistry. 1992 Mar 31;31(12):3177-83. [PubMed:1554703 ]
    11. Varela AS, Bosco Lopez Saez JJ: Utility of serum activity of angiotensin-converting enzyme as a tumor marker. Oncology. 1993 Nov-Dec;50(6):430-5. [PubMed:8233282 ]
    12. Wang P, Polce MJ, Ohanessian G, Wesdemiotis C: The sodium ion affinities of cytosine and its methylated derivatives. J Mass Spectrom. 2008 Apr;43(4):485-94. [PubMed:17994645 ]
    13. Andersson LI, Muller R, Vlatakis G, Mosbach K: Mimics of the binding sites of opioid receptors obtained by molecular imprinting of enkephalin and morphine. Proc Natl Acad Sci U S A. 1995 May 23;92(11):4788-92. [PubMed:7761401 ]
    14. Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic glycylphenylalanine: comparison with the linear form. J Pharm Pharmacol. 1997 Nov;49(11):1067-71. [PubMed:9401939 ]
    15. Ram S, Buchsbaum DJ: Synthesis of a new class of isothiocyanatopeptide bifunctional chelating agents for coupling to monoclonal antibodies. Int J Pept Protein Res. 1996 Jul;48(1):79-86. [PubMed:8844266 ]
    16. Yeagle PL, Dentino AR, Smith FT, Spooner P, Watts A: The antiviral peptide carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine changes the average conformation of phospholipids in membranes. Biochemistry. 1993 Nov 16;32(45):12197-202. [PubMed:8218297 ]
    17. Kelsey DR, Flanagan TD, Young JE, Yeagle PL: Inhibition of Sendai virus fusion with phospholipid vesicles and human erythrocyte membranes by hydrophobic peptides. Virology. 1991 Jun;182(2):690-702. [PubMed:1850923 ]
    18. Kelsey DR, Flanagan TD, Young J, Yeagle PL: Peptide inhibitors of enveloped virus infection inhibit phospholipid vesicle fusion and Sendai virus fusion with phospholipid vesicles. J Biol Chem. 1990 Jul 25;265(21):12178-83. [PubMed:2165053 ]

    PMID: 10668103

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