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Record Information
Version1.0
Created at2007-04-12 20:38:27 UTC
Updated at2021-08-19 20:22:31 UTC
NP-MRD IDNP0000060
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylglutamine
DescriptionN-Acetylglutamine (NAcGln) is a modified amino acid (an acetylated analogue of glutamine) and is a metabolite present in normal human urine. The decomposition products of NAcGln have been identified by NMR and HPLC-MS as N-acetyl-L-glutamic acid, N-(2,6-dioxo-3-piperidinyl) acetamide, pyroglutamic acid, glutamic acid, and glutamine. NAcGln is used for parenteral nutrition as a source of glutamine since glutamine is too unstable whereas NAcGln is very stable. In patients treated with aminoglycosides and/or glycopeptides, an elevation of NAcGln in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.E. N-acetylglutamine) were detected in a patient with aminoacylase I deficiency (EC 3.5.1.14, A homodimeric zinc-binding metalloenzyme located in the cytosol), a novel inborn error of metabolism (PMID:15331932 , 11312773 , 7952062 , 2569664 , 16274666 ).
Structure
Thumb
Synonyms
ValueSource
N~2~-acetyl-L-glutamineChEBI
N-Acetyl-L-glutamineHMDB
AceglutamideHMDB
AcetylglutamineHMDB
NAcGlnHMDB
L-N2-Acetyl-glutamineHMDB
L-N2-AcetylglutamineHMDB
N2-Acetyl-L-glutamineHMDB
N2-AcetylglutamineHMDB
alpha-N-Acetyl-L-glutamineHMDB
Α-N-acetyl-L-glutamineHMDB
(2S)-2-Acetamido-5-amino-5-oxopentanoic acidHMDB
(2S)-4-Carbamoyl-2-acetamidobutanoic acidHMDB
N-AcetylglutamineMeSH
Chemical FormulaC7H12N2O4
Average Mass188.1812 Da
Monoisotopic Mass188.07971 Da
IUPAC Name(2S)-4-carbamoyl-2-acetamidobutanoic acid
Traditional NameN-acetyl-L-glutamine
CAS Registry Number2490-97-3
SMILES
CC(=O)N[C@@H](CCC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12N2O4/c1-4(10)9-5(7(12)13)2-3-6(8)11/h5H,2-3H2,1H3,(H2,8,11)(H,9,10)(H,12,13)/t5-/m0/s1
InChI KeyKSMRODHGGIIXDV-YFKPBYRVSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Chemical Taxonomy
    Description Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
    KingdomOrganic compounds
    Super ClassOrganic acids and derivatives
    ClassCarboxylic acids and derivatives
    Sub ClassAmino acids, peptides, and analogues
    Direct ParentGlutamine and derivatives
    Alternative Parents
    Substituents
    • Glutamine or derivatives
    • N-acyl-alpha-amino acid
    • N-acyl-alpha amino acid or derivatives
    • N-acyl-l-alpha-amino acid
    • N-acyl-l-glutamine
    • Fatty amide
    • Fatty acyl
    • Fatty acid
    • Acetamide
    • Carboxamide group
    • Primary carboxylic acid amide
    • Secondary carboxylic acid amide
    • Carboxylic acid
    • Monocarboxylic acid or derivatives
    • Organonitrogen compound
    • Organic oxide
    • Organopnictogen compound
    • Carbonyl group
    • Organic oxygen compound
    • Organic nitrogen compound
    • Organooxygen compound
    • Hydrocarbon derivative
    • Aliphatic acyclic compound
    Molecular FrameworkAliphatic acyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point197 °CNot Available
    Boiling Point604.00 to 605.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
    Water Solubility155300 mg/L @ 25 °C (est)The Good Scents Company Information System
    LogP-2.635 (est)The Good Scents Company Information System
    Predicted Properties
    PropertyValueSource
    Water Solubility21.9 g/LALOGPS
    logP-2.2ALOGPS
    logP-1.9ChemAxon
    logS-0.93ALOGPS
    pKa (Strongest Acidic)3.76ChemAxon
    pKa (Strongest Basic)-1.4ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count4ChemAxon
    Hydrogen Donor Count3ChemAxon
    Polar Surface Area109.49 ŲChemAxon
    Rotatable Bond Count5ChemAxon
    Refractivity42.55 m³·mol⁻¹ChemAxon
    Polarizability17.81 ųChemAxon
    Number of Rings0ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0006029
    DrugBank IDDB04167
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023808
    KNApSAcK IDNot Available
    Chemspider ID158492
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkAceglutamide
    METLIN IDNot Available
    PubChem Compound182230
    PDB IDNot Available
    ChEBI ID21553
    Good Scents IDrw1597951
    References
    General References
    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. Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
    3. Magnusson I, Kihlberg R, Alvestrand A, Wernerman J, Ekman L, Wahren J: Utilization of intravenously administered N-acetyl-L-glutamine in humans. Metabolism. 1989 Aug;38(8 Suppl 1):82-8. [PubMed:2569664 ]
    4. Bergana MM, Holton JD, Reyzer IL, Snowden MK, Baxter JH, Pound VL: NMR and MS analysis of decomposition compounds produced from N-acetyl-L-glutamine at low pH. J Agric Food Chem. 2000 Dec;48(12):6003-10. [PubMed:11312773 ]
    5. Racine SX, Le Toumelin P, Adnet F, Cohen Y, Cupa M, Hantz E, Le Moyec L: N-acetyl functions and acetate detected by nuclear magnetic resonance spectroscopy of urine to detect renal dysfunction following aminoglycoside and/or glycopeptide antibiotic therapy. Nephron Physiol. 2004;97(4):p53-7. [PubMed:15331932 ]