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Aspartyl-Phenylalanine

July 21, 2017
Common Name

Aspartyl-Phenylalanine Description

Aspartyl-Phenylalanine is a dipeptide composed of aspartate 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

MOLSDFPDBSMILESInChI

Structure for HMDB28760 (Aspartyl-Phenylalanine)

Synonyms

Value Source Asp-pheHMDB Aspartate phenylalanine dipeptideHMDB Aspartate-phenylalanine dipeptideHMDB AspartylphenylalanineHMDB D-F DipeptideHMDB DF DipeptideHMDB L-Aspartyl-L-phenylalanineHMDB

Chemical Formlia

C13H16N2O5 Average Molecliar Weight

280.2765 Monoisotopic Molecliar Weight

280.105921632 IUPAC Name

3-amino-3-[(1-carboxy-2-phenylethyl)carbamoyl]propanoic acid Traditional Name

3-amino-3-[(1-carboxy-2-phenylethyl)carbamoyl]propanoic acid CAS Registry Number

Not Available SMILES

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

InChI Identifier

InChI=1S/C13H16N2O5/c14-9(7-11(16)17)12(18)15-10(13(19)20)6-8-4-2-1-3-5-8/h1-5,9-10H,6-7,14H2,(H,15,18)(H,16,17)(H,19,20)

InChI Key

YZQCXOFQZKCETR-UHFFFAOYSA-N Chemical Taxonomy Classification

Not classified 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-2.46Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.14 mg/mLALOGPS logP-2.4ALOGPS logP-2.8ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)3.17ChemAxon pKa (Strongest Basic)8.53ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area129.72 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity68.45 m3·mol-1ChemAxon Polarizability27.37 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

    HMDB28760 Metagene Link

    HMDB28760 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: EED226

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic dipeptides by the oligopeptide transporter in rat. J Pharm Pharmacol. 1998 Feb;50(2):167-72. [PubMed:9530984 ]
    2. Borke JL, Litwiller RD, Bell MP, Fass DN, McKean DJ, Kumar R: The isolation, characterization and amino terminal sequence of the vitamin D-binding protein (group specific component) from mouse plasma. Int J Biochem. 1988;20(12):1343-9. [PubMed:3243374 ]
    3. Burgert SL, Andersen DW, Stegink LD, Takeuchi H, Schedl HP: Metabolism of aspartame and its L-phenylalanine methyl ester decomposition product by the porcine gut. Metabolism. 1991 Jun;40(6):612-8. [PubMed:1865825 ]
    4. Benoiton NL, Chen FM: 2,4-Dimethyl-5(4H)-oxazolone as reagent for activation and coupling of N-substituted aspartic acid. Int J Pept Protein Res. 1994 Aug;44(2):139-42. [PubMed:7982757 ]
    5. Goodman M, Mattern RH, Gantzel P, Santini A, Iacovino R, Saviano M, Benedetti E: X-ray structures of new dipeptide taste ligands. J Pept Sci. 1998 Jun;4(4):229-38. [PubMed:9680057 ]
    6. Pattanaargson S, Sanchavanakit C: Aspartame degradation study using electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(11):987-93. [PubMed:10844736 ]
    7. Schwerdt G, Freudinger R, Silbernagl S, Gekle M: Apical uptake of radiolabelled ochratoxin A into Madin-Darby canine kidney cells. Toxicology. 1998 Nov 16;131(2-3):193-202. [PubMed:9928634 ]
    8. Leung SS, Grant DJ: Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine. J Pharm Sci. 1997 Jan;86(1):64-71. [PubMed:9002461 ]

    PMID: 11399662

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