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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, 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
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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
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 ]