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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 20:38:27 UTC
Update Date2020-02-26 21:26:11 UTC
HMDB IDHMDB0006029
Secondary Accession Numbers
  • HMDB06029
Metabolite 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
Data?1582752371
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
N-AcetylglutamineMeSH
(2S)-2-Acetamido-5-amino-5-oxopentanoic acidHMDB
(2S)-4-Carbamoyl-2-acetamidobutanoic acidHMDB
Chemical FormulaC7H12N2O4
Average Molecular Weight188.1812
Monoisotopic Molecular Weight188.079706882
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
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
Ontology
Disposition

Biological location:

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)-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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0udi-0792000000-c1b9c0a2e401b09330e3Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0pir-0940000000-273a364e0545e1c9660cSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0aor-1930000000-34e50f564c94c8d7eecfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aor-1930000000-3417e5b740846b106d28Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aos-1910000000-40c3f40b74f5a900e804Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-80e55e189a017060034bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007d-0900000000-737775fcc86ca482b84fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmj-1900000000-f6b8dadcb62c0bd29b4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0feb-9500000000-6dbd187babd525f439e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5808e02fdf0b59805441Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-3900000000-d91260dd274a3a963a02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-db717deb0ee2153fbc4cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB04167
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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