GABAReceptorInhibitorgabareceptorinhibitor

N-Acetyl-L-phenylalanine

By rofalproject
Common Name

N-Acetyl-L-phenylalanine Description

Acetylphenylalanine is a hazardous amphipathic metabolite of phenylalanine. It appears in large amount in urine of patients with phenylketonuria which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine. Acetylphenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] in the pathway phenylalanine metabolism. (KEGG; Wikipedia). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Acetyl-L-phenylalanineChEBI AcetylphenylalanineChEBI L-N-AcetylphenylalanineChEBI N-AcetylphenylalanineChEBI N-Acetyl-3-phenyl-L-alanineHMDB N-Acetyl-L-phenalanineHMDB

Chemical Formlia

C11H13NO3 Average Molecliar Weight

207.2258 Monoisotopic Molecliar Weight

207.089543287 IUPAC Name

(2S)-2-acetamido-3-phenylpropanoic acid Traditional Name

acetyl-L-phenylalanine CAS Registry Number

2018-61-3 SMILES

CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1

InChI Key

CBQJSKKFNMDLON-JTQLQIEISA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resliting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Phenylalanine and derivatives Alternative Parents

  • N-acyl-alpha amino acids
  • Phenylpropanoic acids
  • Amphetamines and derivatives
  • Propargyl-type 1,3-dipolar organic compounds
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Carboximidic acids
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • N-acetyl-L-amino acid (CHEBI:16259 )
  • N-acetylphenylalanine (CHEBI:16259 )
  • N-acyl-L-phenylalanine (CHEBI:16259 )

    • Ontology Status

    Detected but not Quantified Origin

  • Endogenous

    • Biofunction

  • Protein synthesis, amino acid biosynthesis

    • Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point171 – 173 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP0.93GREEN,PG ET AL. (1991)

    Predicted Properties

    Property Value Source Water Solubility0.97 mg/mLALOGPS logP1.11ALOGPS logP0.9ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)4.02ChemAxon pKa (Strongest Basic)-1.5ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area66.4 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity54.56 m3·mol-1ChemAxon Polarizability21.22 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-MS (2 TMS)splash10-00kf-3980000000-205dc96635b498baa46cView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (1 TMS)splash10-00dl-3920000000-50af7cdc34df34b89e91View in MoNA Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0fr7-1950000000-8c9c63efeb473bcf7625View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0fr7-1950000000-8c9c63efeb473bcf7625View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-00dl-2920000000-f0ce2160cf1eb9d38d56View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0f6x-2910000000-33afe725162942dc296aView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0f6x-2910000000-33afe725162942dc296aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-9e69c187ac8560365826View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-014i-0900000000-04559809a9c6261f18b6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-5900000000-a8bb0fc573e6143527aaView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0090000000-2dcdf0ed503251026e40View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-2920000000-7447f1e30d868cae5af6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0lxy-8900000000-3b53da8f8106adfdd677View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0pbc-9400000000-1737db9a05bf29f3701aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9100000000-f015dd2066ebbefec15aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4l-1960000000-20faf15c3d02bbe80ad2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-891ecddb54dab32f4dceView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-1900000000-6867cba730dee8712265View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-2900000000-2e77f5a51bec17ed674eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-4900000000-c9aadc8231b14121aa8cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-02tc-0900000000-ac3b438665d0b035a7e2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-a426a7fbff06e9213f59View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-0d8dd7876525745785ffView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0fdo-6900000000-ad4d31f8b5e3e0474416View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0pbc-9400000000-5ac323188cccce720870View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00di-1900000000-66240358c350223051f0View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • 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

    FDB022084 KNApSAcK ID

    Not Available Chemspider ID

    67404 KEGG Compound ID

    C03519 BioCyc ID

    PHE BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00512 Metagene Link

    HMDB00512 METLIN ID

    5498 PubChem Compound

    74839 PDB ID

    Not Available ChEBI ID

    16259

    Product: YM-58483

    References Synthesis Reference Borovicka, Milos; Cervinka, Otakar; Gajewski, Karel; Lukac, Juraj. Isolation of optically pure N-acetyl-L-phenylalanine after enantioselective hydrogenation of N-acetamidocinnamic acid. Czech. (1985), 2 pp. Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. [PubMed:12013218 ]
    2. Mach H, Middaugh CR, Lewis RV: Detection of proteins and phenol in DNA samples with second-derivative absorption spectroscopy. Anal Biochem. 1992 Jan;200(1):20-6. [PubMed:1375815 ]
    3. Okajima K, Inoue M, Morino Y: Studies on the mechanism for renal elimination of N-acetylphenylalanine: its pathophysiologic significance in phenylketonuria. J Lab Clin Med. 1985 Jan;105(1):132-8. [PubMed:4038506 ]

    Enzymes

    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
    Gene Name:
    GLYATL1
    Uniprot ID:
    Q969I3
    Molecular weight:
    35100.895
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
    Gene Name:
    GLYATL2
    Uniprot ID:
    Q8WU03
    Molecular weight:
    34277.055

    PMID: 24951278

    By rofalproject

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