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Phenylalanyl-Alanine

July 21, 2017
Common Name

Phenylalanyl-Alanine Description

Phenylalanyl-Alanine is a dipeptide composed of phenylalanine and alanine. 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 HMDB28988 (Phenylalanyl-Alanine)

Synonyms

Value Source F-a DipeptideHMDB FA dipeptideHMDB L-Phenylalanyl-L-alanineHMDB Phe-alaHMDB Phenylalanine alanine dipeptideHMDB Phenylalanine-alanine dipeptideHMDB PhenylalanylalanineHMDB

Chemical Formlia

C12H16N2O3 Average Molecliar Weight

236.267 Monoisotopic Molecliar Weight

236.116092388 IUPAC Name

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

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

Not Available SMILES

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

InChI Identifier

InChI=1S/C12H16N2O3/c1-8(12(16)17)14-11(15)10(13)7-9-5-3-2-4-6-9/h2-6,8,10H,7,13H2,1H3,(H,14,15)(H,16,17)

InChI Key

MIDZLCFIAINOQN-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
  • Alanine and derivatives
  • Amphetamines and derivatives
  • Aralkylamines
  • Fatty amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • 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-1.72Extrapolated

    Predicted Properties

    Property Value Source Water Solubility2.43 mg/mLALOGPS logP-0.98ALOGPS logP-1.7ChemAxon logS-2ALOGPS pKa (Strongest Acidic)3.73ChemAxon pKa (Strongest Basic)8.01ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity62.41 m3·mol-1ChemAxon Polarizability24.71 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

    HMDB28988 Metagene Link

    HMDB28988 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Shogaol

    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. Dunbar RC, Steill JD, Polfer NC, Oomens J: Peptide length, steric effects, and ion solvation govern zwitterion stabilization in barium-chelated di- and tripeptides. J Phys Chem B. 2009 Aug 6;113(31):10552-4. doi: 10.1021/jp905060n. [PubMed:19606889 ]
    3. Polfer NC, Oomens J, Dunbar RC: Alkali metal complexes of the dipeptides PheAla and AlaPhe: IRMPD spectroscopy. Chemphyschem. 2008 Mar 14;9(4):579-89. doi: 10.1002/cphc.200700700. [PubMed:18293344 ]
    4. Baboshina OV, Crinelli R, Siepmann TJ, Haas AL: N-end rule specificity within the ubiquitin/proteasome pathway is not an affinity effect. J Biol Chem. 2001 Oct 19;276(42):39428-37. Epub 2001 Aug 7. [PubMed:11493606 ]
    5. Lawson TG, Sweep ME, Schlax PE, Bohnsack RN, Haas AL: Kinetic analysis of the conjugation of ubiquitin to picornavirus 3C proteases catalyzed by the mammalian ubiquitin-protein ligase E3alpha. J Biol Chem. 2001 Oct 26;276(43):39629-37. Epub 2001 Aug 28. [PubMed:11526102 ]
    6. 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 ]
    7. Dufour E, Storer AC, Menard R: Engineering nitrile hydratase activity into a cysteine protease by a single mutation. Biochemistry. 1995 Dec 19;34(50):16382-8. [PubMed:8845364 ]
    8. Naik RM, Srivastava A, Prasad S: Highly sensitive catalytic spectrophotometric determination of ruthenium. Spectrochim Acta A Mol Biomol Spectrosc. 2008 Jan;69(1):193-7. Epub 2007 Mar 24. [PubMed:17574906 ]
    9. Chen JJ, Barber LA, Dymshitz J, Vasko MR: Peptidase inhibitors improve recovery of substance P and calcitonin gene-related peptide release from rat spinal cord slices. Peptides. 1996;17(1):31-7. [PubMed:8822507 ]
    10. Matsubara T, Fujita R, Sugiyama S, Kawashiro K: Stability of protease in organic solvent: structural identification by solid-state NMR of lyophilized papain before and after 1-propanol treatment and the corresponding enzymatic activities. Biotechnol Bioeng. 2006 Apr 5;93(5):928-33. [PubMed:16329143 ]
    11. Roper H, Roper S, Meyer B: Amadori- and N-nitroso-Amadori compounds and their pyrolysis products. Chemical, analytical and biological aspects. IARC Sci Publ. 1984;(57):101-11. [PubMed:6398292 ]
    12. Frade RF, Candeias NR, Duarte CM, Andre V, Duarte MT, Gois PM, Afonso CA: New dirhodium complex with activity towards colorectal cancer. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3413-5. doi: 10.1016/j.bmcl.2010.04.002. Epub 2010 Apr 9. [PubMed:20434912 ]

    PMID: 12485205

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