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Glycyl-Phenylalanine

July 21, 2017
Common Name

Glycyl-Phenylalanine Description

Glycyl-Phenylalanine is a dipeptide composed of glycine and phenylalanine. 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 HMDB28848 (Glycyl-Phenylalanine)

Synonyms

Value Source g-F DipeptideHMDB GF DipeptideHMDB Gly-pheHMDB Glycine phenylalanine dipeptideHMDB Glycine-phenylalanine dipeptideHMDB GlycylphenylalanineHMDB L-Glycyl-L-phenylalanineHMDB Gly-D-phenylalanineMeSH Glycyl-D-phenylalanineMeSH Glycylphenylalanine, (L)-isomerMeSH Glycylphenylalanine, (D)-isomerMeSH Gly-L-phenylalanineMeSH Glycyl-L-phenylalanineMeSH Glycylphenylalanine monobrosylate, (L)-isomerMeSH Glycylphenylalanine monohydrochloride, monohydrate, (L)-isomerMeSH Glycylphenylalanine monotosylate, (L)-isomerMeSH

Chemical Formlia

C11H14N2O3 Average Molecliar Weight

222.2405 Monoisotopic Molecliar Weight

222.100442324 IUPAC Name

2-(2-aminoacetamido)-3-phenylpropanoic acid Traditional Name

2-(2-aminoacetamido)-3-phenylpropanoic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

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

InChI Key

JBCLFWXMTIKCCB-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
  • Phenylpropanoic acids
  • Amphetamines and derivatives
  • 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 or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • 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

    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-2.29Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.21 mg/mLALOGPS logP-1.1ALOGPS logP-2.3ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)3.73ChemAxon pKa (Strongest Basic)8.14ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity57.92 m3·mol-1ChemAxon Polarizability22.6 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

  • Saliva

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details SalivaDetected but not Quantified Adlit (>18 years old)Male

    Normal

  • 22308371

    • details

    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

    HMDB28848 Metagene Link

    HMDB28848 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: AK-1

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Rai DK, Mooney A, Kenny PT: A tandem mass spectrometric investigation of N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters. Rapid Commun Mass Spectrom. 2011 Oct 15;25(19):2905-10. doi: 10.1002/rcm.5184. [PubMed:21913269 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]
    5. Turecek F, Syrstad EA, Seymour JL, Chen X, Yao C: Peptide cation-radicals. A computational study of the competition between peptide N-Calpha bond cleavage and loss of the side chain in the [GlyPhe-NH2 + 2H]+. cation-radical. J Mass Spectrom. 2003 Oct;38(10):1093-104. [PubMed:14595859 ]
    6. Anderson L, Bussler B, Martins H, Dufton M: Enkephalin-processing oligopeptidases in cobra venom: inhibition by thiorphan and bestatin reveals co-operative actions. Toxicon. 1998 May;36(5):719-28. [PubMed:9655632 ]
    7. Duman JG, Chen L, Palmer AE, Hille B: Contributions of intracellular compartments to calcium dynamics: implicating an acidic store. Traffic. 2006 Jul;7(7):859-72. [PubMed:16787398 ]
    8. 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 ]
    9. Lopez JJ, Camello-Almaraz C, Pariente JA, Salido GM, Rosado JA: Ca2+ accumulation into acidic organelles mediated by Ca2+- and vacuolar H+-ATPases in human platelets. Biochem J. 2005 Aug 15;390(Pt 1):243-52. [PubMed:15847604 ]
    10. Tobin MB, Cole SC, Miller JR, Baldwin JE, Sutherland JD: Amino-acid substitutions in the cleavage site of acyl-coenzyme A:isopenicillin N acyltransferase from Penicillium chrysogenum: effect on proenzyme cleavage and activity. Gene. 1995 Aug 30;162(1):29-35. [PubMed:7557412 ]

    PMID: 9369342

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