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Phenylalanyl-Serine

July 21, 2017
Common Name

Phenylalanyl-Serine Description

Phenylalanyl-Serine is a dipeptide composed of phenylalanine and serine. 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 HMDB29004 (Phenylalanyl-Serine)

Synonyms

Value Source F-S DipeptideHMDB FS DipeptideHMDB L-Phenylalanyl-L-serineHMDB Phe-serHMDB Phenylalanine serine dipeptideHMDB Phenylalanine-serine dipeptideHMDB PhenylalanylserineHMDB

Chemical Formlia

C12H16N2O4 Average Molecliar Weight

252.2664 Monoisotopic Molecliar Weight

252.11100701 IUPAC Name

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

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

Not Available SMILES

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

InChI Identifier

InChI=1S/C12H16N2O4/c13-9(6-8-4-2-1-3-5-8)11(16)14-10(7-15)12(17)18/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)

InChI Key

ROHDXJUFQVRDAV-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
  • Serine and derivatives
  • Alpha amino acid amides
  • Amphetamines and derivatives
  • Aralkylamines
  • Beta hydroxy acids and derivatives
  • Fatty amides
  • Secondary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds
  • Primary alcohols

    • Substituents

  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Beta-hydroxy acid
  • Aralkylamine
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty amide
  • Hydroxy acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen 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-2.77Extrapolated

    Predicted Properties

    Property Value Source Water Solubility3.89 mg/mLALOGPS logP-2.1ALOGPS logP-2.8ChemAxon logS-1.8ALOGPS pKa (Strongest Acidic)3.55ChemAxon pKa (Strongest Basic)8.01ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area112.65 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity63.96 m3·mol-1ChemAxon Polarizability25.72 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

    HMDB29004 Metagene Link

    HMDB29004 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Fluorescein-5-maleimide

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Mizuma T, Narasaka T, Awazu S: Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1. J Pharm Pharmacol. 2002 Sep;54(9):1293-6. [PubMed:12356285 ]
    2. Mizuma T, Narasaka T, Awazu S: Concentration-dependent atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Biol Pharm Bull. 2003 Nov;26(11):1625-8. [PubMed:14600416 ]
    3. Schwarz A, Steinke D, Kula MR, Wandrey C: Optimization of enzyme-mediated peptide bond formation. Biotechnol Appl Biochem. 1990 Apr;12(2):188-95. [PubMed:2109983 ]
    4. Behling RA, Fischer AG: Formation of phenylalanylserine and cyclo-phenylalanylseryl by protoplasts of Gliocladium virens. Int J Biochem. 1980;11(5):457-8. [PubMed:6156101 ]
    5. Bucevic-Popovic V, Pavela-Vrancic M, Dieckmann R, Von Dohren H: Relationship between activating and editing functions of the adenylation domain of apo-tyrocidin synthetase 1 (apo-TY1). Biochimie. 2006 Mar-Apr;88(3-4):265-70. Epub 2005 Sep 15. [PubMed:16182433 ]
    6. Mizuma T, Narasaka T, Hiyoshi W, Awazu S: Concentration-dependent preferences of absorptive and excretive transport cause atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Res Commun Mol Pathol Pharmacol. 2002;111(5-6):199-209. [PubMed:15244036 ]

    PMID: 17059817

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