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Showing Compound N-Acetylglutamine (FDB023808)

Record Information
Version1.0
Creation date2011-09-21 00:35:01 UTC
Update date2015-10-09 22:33:39 UTC
Primary IDFDB023808
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number2490-97-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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, HMDB
N-AcetylglutamineChEBI
alpha-n-acetyl-l-glutaminehmdb
L-N2-acetyl-Glutaminehmdb
N-acetyl-l-glutaminehmdb
N2-acetylglutaminehmdb
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
Polarizability17.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H12N2O4
IUPAC name4-carbamoyl-2-acetamidobutanoic acid
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
Isomeric SMILESCC(=O)NC(CCC(N)=O)C(O)=O
Average Molecular Weight188.1812
Monoisotopic Molecular Weight188.079706882
Classification
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
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-Acetylglutamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-80e55e189a017060034bSpectrum
Predicted GC-MSN-Acetylglutamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9110000000-c1484214f430e9c081e6Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007d-0900000000-737775fcc86ca482b84f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmj-1900000000-f6b8dadcb62c0bd29b4b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0feb-9500000000-6dbd187babd525f439e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5808e02fdf0b598054412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-3900000000-d91260dd274a3a963a022016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-db717deb0ee2153fbc4c2016-08-03View Spectrum
NMRNot Available
ChemSpider ID23836
ChEMBL IDCHEMBL3184604
KEGG Compound IDNot Available
Pubchem Compound ID25561
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06029
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference