Nalpha-Acetyl-L-glutamine (CHEM020175)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:52:57 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020175
Identification
Common NameNalpha-Acetyl-L-glutamine
ClassSmall Molecule
DescriptionAn N(2)-acetylglutamine that has L-configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Molecular Mass188.181 g/mol
Monoisotopic Mass188.080 g/mol
CAS Registry Number2490-97-3
IUPAC Name(2S)-4-carbamoyl-2-acetamidobutanoic acid
Traditional NameN-acetyl-L-glutamine
SMILESCC(=O)NC(CCC(N)=O)C(O)=O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-1b58f8cf05ca3b4d60f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-d41b772a35f0471d4819Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-01qi-1920000000-03cc5cde7404917c4444Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001l-9000000000-ae8475f16758af00d088Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001r-2910000000-03b515be8545a7a4c32aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9810000000-4b20d607fd6455a3cc90Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-0900000000-85c4ed15c285d61aaf77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3900000000-a9b7bc3049cf72cfb344Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-1bfaeb4c12c7be0bca43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-d1234af7f81ed8eb8936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6s-7900000000-d2a7387e0ea87eed3146Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-67fd7588646f70a13dbfSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04167
HMDB IDHMDB0006029
FooDB IDFDB023808
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAceglutamide
Chemspider ID158492
ChEBI ID21553
PubChem Compound ID182230
Kegg Compound IDNot Available
YMDB IDYMDB01757
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11312773
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15331932
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17253138
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=5747861
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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.