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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 20:38:27 UTC
Update Date2017-10-23 19:04:19 UTC
HMDB IDHMDB0006029
Secondary Accession Numbers
  • HMDB06029
Metabolite Identification
Common NameN-Acetylglutamine
DescriptionN-Acetylglutamine (GIcNAc) is a modified amino acid (an acetylated analogue of glutamine), a metabolite present in normal human urine. The decomposition products of GIcNAc 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. GIcNAc is used for parenteral nutrition as a source of glutamine, since glutamine is too unstable, but GIcNAc is very stable. In patients treated with aminoglycosides and/or glycopeptides, elevation GIcNAc in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e.: N-Acetylglutamine) were detected 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
AceglutamideChEBI
AcetylglutamineChEBI
GlcNAcChEBI
AceglutamidHMDB
alpha-N-Acetyl-L-glutamineHMDB
L-2-Acetamidoglutaramic acidHMDB
L-N2-Acetyl-glutamineHMDB
N-Acetyl-L-glutamineHMDB
N2-Acetyl-L-glutamineHMDB
N2-AcetylglutamineHMDB
Aceglutamide, aluminum (3:1) saltMeSH
Chemical FormulaC7H12N2O4
Average Molecular Weight188.1812
Monoisotopic Molecular Weight188.079706882
IUPAC Name4-carbamoyl-2-acetamidobutanoic acid
Traditional NameN-acetyl-L-glutamine
CAS Registry Number2490-97-3
SMILES
CC(=O)NC(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)
InChI KeyKSMRODHGGIIXDV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glutamine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 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
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point197 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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)-0.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.55 m³·mol⁻¹ChemAxon
Polarizability17.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-80e55e189a017060034bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9110000000-c1484214f430e9c081e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007d-0900000000-737775fcc86ca482b84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmj-1900000000-f6b8dadcb62c0bd29b4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0feb-9500000000-6dbd187babd525f439e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5808e02fdf0b59805441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-3900000000-d91260dd274a3a963a02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-db717deb0ee2153fbc4cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified18.557 +/- 7.493 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)FemaleEpithelial ovarian cancer details
UrineDetected and Quantified36.587 +/- 55.035 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023808
KNApSAcK IDNot Available
Chemspider ID23836
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25561
PDB IDNot Available
ChEBI ID73685
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate).
Gene Name:
ACY1
Uniprot ID:
Q03154
Molecular weight:
45884.705