GABAReceptorInhibitorgabareceptorinhibitor

Acetylglycine

By rofalproject
Common Name

Acetylglycine Description

N-Acetylglycine is used is in biological research of peptidomimetics. It is used as the blocking agent of the N-terminus to prepare unnatural and unusual amino acids and amino acid analogs as well as to modify peptides. N-Substituted glycine analogs are widely used in peptidomimetics and drug research. Excessive amounts N-acetyl amino acids including N-acetylglycine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, Nacetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine) can be detected in the urine with individuals with Acylase I defiency. This enzyme is involved in the degradation of N-acylated proteins. Individuals with this disorder will experience convlisions, hearing loss ond difficlity feeding. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Ac-gly-OHChEBI Acetamidoacetic acidChEBI Aceturic acidChEBI acetylamino-Acetic acidChEBI Acetylaminoacetic acidChEBI Ethanoylaminoethanoic acidChEBI AcetamidoacetateGenerator AcetateGenerator Acetic acidGenerator acetylamino-AcetateGenerator AcetylaminoacetateGenerator EthanoylaminoethanoateGenerator 15N-Acetylglycine a-radicalHMDB 2-AcetamidoacetateHMDB 2-Acetamidoacetic acidHMDB Ac glyHMDB AceturateHMDB AcetylglycocollHMDB N-Acetyl-glycineHMDB N-AcetylglycineHMDB N-Acetylglycine sodium saltHMDB AcetylglycinateMeSH

Chemical Formlia

C4H7NO3 Average Molecliar Weight

117.1033 Monoisotopic Molecliar Weight

117.042593095 IUPAC Name

2-acetamidoacetic acid Traditional Name

aceturate CAS Registry Number

543-24-8 SMILES

CC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)

InChI Key

OKJIRPAQVSHGFK-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

N-acyl-alpha amino acids Alternative Parents

  • 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

  • N-acyl-alpha-amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • N-acylglycine (CHEBI:40410 )
  • N-acetyl-amino acid (CHEBI:40410 )

    • Ontology Status

    Detected and 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 Point207 – 209 °CNot Available Boiling PointNot AvailableNot Available Water Solubility26.3 mg/mL at 15 °CNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility51.3 mg/mLALOGPS logP-0.89ALOGPS logP-1.3ChemAxon logS-0.36ALOGPS pKa (Strongest Acidic)3.77ChemAxon pKa (Strongest Basic)-1.6ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area66.4 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity25.45 m3·mol-1ChemAxon Polarizability10.69 Å3ChemAxon Number of Rings0ChemAxon 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 (1 TMS)splash10-0ff1-0900000000-7f59efc7318abb307de5View in MoNA GC-MS

    GC-MS Spectrum – EI-Bsplash10-008c-9000000000-c8db9b668b0e8c255556View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-e0f8be2f6c11bf3ffb19View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-b3dd5f7718c7ca2f137aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7b4e818e7fb8f7ad37feView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9300000000-fa29c9711fbb33529360View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-01b9-7900000000-1477d110314b9fcbf541View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-016r-9700000000-a6a0c2dacd758a89690eView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-056r-9100000000-41073c517efcd76b3e9bView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-054o-9000000000-3586ff7ce2dbe6b00d8bView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-01b9-9800000000-4671448e0c1ab50647adView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-00xr-9300000000-0903cfde2598dd206fd8View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-05fu-9000000000-3804a2ffeab504193078View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

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

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Saliva
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified69.7 uMAdlit (>18 years old)BothNormal

  • 21359215

    • details BloodDetected and Quantified109.44 +/- 85.64 uMAdlit (>18 years old)Not SpecifiedNormal

  • 18953024

    • details SalivaDetected and Quantified56.76 +/- 35.67 uMAdlit (>18 years old)BothNormal

  • Zerihun T. Dame, …

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details UrineDetected and Quantified170 +/- 18 nmol/mmol creatinineInfant (0-1 year old)MaleAminoacylase I deficiency

  • 16274666
  • 16351159

    • details

    Associated Disorders and Diseases Disease References

    Aminoacylase I deficiency

    1. Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
    2. A J, Trygg J, Glilberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [PubMed:16351159 ]

    Associated OMIM IDs

  • 609924 (Aminoacylase I deficiency)

    • 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

    FDB022100 KNApSAcK ID

    Not Available Chemspider ID

    10507 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00532 Metagene Link

    HMDB00532 METLIN ID

    5517 PubChem Compound

    10972 PDB ID

    AAC ChEBI ID

    40410

    Product: 7beta-Hydroxylathyrol

    References Synthesis Reference Lin, Jiang Jen; Knifton, John F.; Yeakey, Ernest L. Preparation of N-acetylglycine. U.S. (1990), 5 pp. Material Safety Data Sheet (MSDS) Download (PDF) General References Not Available

    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: 20980592

    By rofalproject

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