N-Acetyl-L-glutamic acid (CHEM019066)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:47:42 UTC
Update Date2016-11-09 01:15:55 UTC
Accession NumberCHEM019066
Identification
Common NameN-Acetyl-L-glutamic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2-(Acetylamino)pentanedioic acidChEBI
Ac-glu-OHChEBI
Acetyl-L-glutamic acidChEBI
Acetylglutamic acidChEBI
L-N-Acetylglutamic acidChEBI
N-Ac-glu-OHChEBI
N-ACETYL-L-glutamATEChEBI
N-Acetylglutamic acidChEBI
(S)-2-(Acetylamino)pentanedioateGenerator
Acetyl-L-glutamateGenerator
AcetylglutamateGenerator
L-N-AcetylglutamateGenerator
N-AcetylglutamateGenerator
N-Acetylglutamic acid semialdehydeHMDB
N-Acetylglutamate, potassium salt, (L)-isomerHMDB
N-Acetylglutamate, (D)-isomerHMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomerHMDB
N-Acetylglutamate, dipotassium salt, (L)-isomerHMDB
N-Acetylglutamate, disodium salt, (L)-isomerHMDB
N-Acetylglutamate, calcium salt, (L)-isomerHMDB
N-Acetylglutamate, magnesium salt, (L)-isomerHMDB
Sodium N-acetylglutamateHMDB
N-Acetylglutamate, (DL)-isomerHMDB
N-Acetylglutamate, monosodium salt, (L)-isomerHMDB
N-Acetyl-L-glutaminic acidHMDB
alpha-(N-Acetyl)-L-glutamic acidHMDB
Α-(N-acetyl)-L-glutamic acidHMDB
NAcGluHMDB
N-Acetyl-L-glutamic acidGenerator, KEGG
Chemical FormulaC7H11NO5
Average Molecular Mass189.166 g/mol
Monoisotopic Mass189.064 g/mol
CAS Registry Number1188-37-0
IUPAC Name(2S)-2-acetamidopentanedioic acid
Traditional NameN-acetyl-L-glutamate
SMILESCC(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI IdentifierInChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChI KeyRFMMMVDNIPUKGG-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 Solubility18.6 g/LALOGPS
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m³·mol⁻¹ChemAxon
Polarizability17.44 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 (3 TMS)splash10-0a4i-1940000000-78ee4843d1eab79c7ca3Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0api-3930000000-e499004b087e5d741b02Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-2d39b0eff0ff23756843Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aor-1920000000-a2fe62d19e50f9db103fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-546571923f012476b58bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ap0-1910000000-d18f7c4035b189c1f4b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4r-1900000000-fc8347700abd012bf349Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-cdb488a97c5bf1952810Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1f9f80a37aa4e37ee878Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-0900000000-5423b76f7eb4b2a17facSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-38410c884a2999611065Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-9700000000-85acd9611312dd7df0dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9100000000-0d780e23d772cf133da2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0ufr-1900000000-7a57de84cf9c6671cfc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-7b58c7204405ece93fcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-515b33cc5674fc8985c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-b379a6e4d794e810c478Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2ce098bb9e1b35433878Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8e7d8abde262b7d5cb45Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-a3bdc3627857c5f47f4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-2900000000-b074eaccd0b3864766b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0fb9-0900000000-54faa7b7182f5cceca84Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-0f14d0a7c8fb67a381b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-9000000000-333b6aa44450dbd0c754Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-adf2d3645b4231cbddc3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-d7df112ff7af7e076d70Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-d70c37086adaa1636750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-88345aaf9776c7fb8676Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-2900000000-5fca3bd987ebf6b42946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9500000000-be58124b136b37456414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a56ffb8d475d132443a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-2900000000-c32612499c0a2ceb8298Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-75dbbc130d00cfec5880Spectrum
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
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D 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 IDDB04075
HMDB IDHMDB0001138
FooDB IDFDB031019
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDACETYL-GLU
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkN-Acetylglutamic_acid
Chemspider ID64077
ChEBI ID17533
PubChem Compound ID70914
Kegg Compound IDC00624
YMDB IDYMDB00066
ECMDB IDECMDB21429
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.
2. hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.
3. Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8.
4. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1.
5. 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.
6. Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12.
7. Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46.
8. 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.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=115331
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5924663
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6035272
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9037750