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N-acetyl-L-glutamic acid (YMDB00066)

Identification
YMDB IDYMDB00066
NameN-acetyl-L-glutamic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-Acetyl-L-glutamic acid, also known as acetylglutamate or ac-glu-OH, 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. N-Acetyl-L-glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-2-(acetylamino)pentanedioate
  • 2-acetamido-L-Glutaraldehydate
  • 2-acetamido-L-Glutaraldehydic acid
  • Ac-Glu-OH
  • acetyl-glutamate
  • Acetyl-L-glutamate
  • Acetyl-L-glutamic acid
  • acetylglutamate
  • acetylglutamic acid
  • DL-Acetylglutamate
  • DL-Acetylglutamic acid
  • L-Glutamic acid, N-acetyl-
  • N-Ac-Glu-OH
  • N-acetyl L-glutamate
  • N-acetyl L-glutamic acid
  • N-Acetyl-DL-glutamate
  • N-Acetyl-DL-glutamic acid
  • N-acetyl-Glutamate
  • N-acetyl-Glutamic acid
  • N-Acetyl-L-glutamate
  • N-Acetyl-L-glutamic acid
  • N-Acetyl-L-glutamic acid-gamma-semialdehyde
  • N-Acetylglutamate
  • N-Acetylglutamic acid
  • N-Acetylglutamic gamma-semialdehyde
  • NAG
  • (S)-2-(Acetylamino)pentanedioic acid
  • L-N-Acetylglutamic acid
  • L-N-Acetylglutamate
  • N-Acetylglutamic acid semialdehyde
  • N-Acetylglutamate, potassium salt, (L)-isomer
  • N-Acetylglutamate, (D)-isomer
  • N-Acetylglutamate, calcium salt (1:1), (L)-isomer
  • N-Acetylglutamate, dipotassium salt, (L)-isomer
  • N-Acetylglutamate, disodium salt, (L)-isomer
  • N-Acetylglutamate, calcium salt, (L)-isomer
  • N-Acetylglutamate, magnesium salt, (L)-isomer
  • Sodium N-acetylglutamate
  • N-Acetylglutamate, (DL)-isomer
  • N-Acetylglutamate, monosodium salt, (L)-isomer
  • N-Acetyl-L-glutaminic acid
  • alpha-(N-Acetyl)-L-glutamic acid
  • Α-(N-acetyl)-L-glutamic acid
  • NAcGlu
CAS number1188-37-0
WeightAverage: 189.1659
Monoisotopic: 189.063722467
InChI KeyRFMMMVDNIPUKGG-YFKPBYRVSA-N
InChIInChI=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
IUPAC Name(2S)-2-acetamidopentanedioic acid
Traditional IUPAC NameN-acetyl-L-glutamate
Chemical FormulaC7H11NO5
SMILESCC(=O)N[C@@H](CCC(O)=O)C(O)=O
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
Physical Properties
StateSolid
Charge0
Melting point199 - 201 °C
Experimental Properties
PropertyValueReference
Water Solubility52 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + N-acetyl-L-glutamic acid → N-Acetyl-L-glutamyl 5-phosphate + ADP
Acetyl-CoA + L-Glutamic acid → N-acetyl-L-glutamic acid + hydron + Coenzyme A
L-Glutamic acid + N-Acetylornithine → N-acetyl-L-glutamic acid + Ornithine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1940000000-78ee4843d1eab79c7ca3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0api-3930000000-e499004b087e5d741b02JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-2d39b0eff0ff23756843JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aor-1920000000-a2fe62d19e50f9db103fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-0920000000-546571923f012476b58bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ap0-1910000000-d18f7c4035b189c1f4b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4r-1900000000-fc8347700abd012bf349JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-cdb488a97c5bf1952810JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1f9f80a37aa4e37ee878JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-0900000000-5423b76f7eb4b2a17facJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-38410c884a2999611065JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-9700000000-85acd9611312dd7df0dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9100000000-0d780e23d772cf133da2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0ufr-1900000000-7a57de84cf9c6671cfc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-7b58c7204405ece93fcaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-515b33cc5674fc8985c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-b379a6e4d794e810c478JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2ce098bb9e1b35433878JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8e7d8abde262b7d5cb45JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-a3bdc3627857c5f47f4bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-2900000000-b074eaccd0b3864766b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0fb9-0900000000-54faa7b7182f5cceca84JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-0f14d0a7c8fb67a381b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-9000000000-333b6aa44450dbd0c754JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-adf2d3645b4231cbddc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-d7df112ff7af7e076d70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-d70c37086adaa1636750JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-88345aaf9776c7fb8676JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-2900000000-5fca3bd987ebf6b42946JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9500000000-be58124b136b37456414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a56ffb8d475d132443a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-2900000000-c32612499c0a2ceb8298JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-75dbbc130d00cfec5880JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Abadjieva, A., Pauwels, K., Hilven, P., Crabeel, M. (2001). "A new yeast metabolon involving at least the two first enzymes of arginine biosynthesis: acetylglutamate synthase activity requires complex formation with acetylglutamate kinase." J Biol Chem 276:42869-42880.11553611
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.
External Links:
ResourceLink
CHEBI ID17533
HMDB IDHMDB01138
Pubchem Compound ID185
Kegg IDC00624
ChemSpider ID64077
FOODB IDFDB031019
WikipediaN-Acetylglutamic_acid
BioCyc IDACETYL-GLU

Enzymes

Protein Details
1. Arginine biosynthesis bifunctional protein ArgJ, mitochondrial
General function:
Involved in glutamate N-acetyltransferase activity
Specific function:
Catalyzes two activities which are involved in the cyclic version of arginine biosynthesis:the synthesis of acetylglutamate from glutamate and acetyl-CoA, and of ornithine by transacetylation between acetylornithine and glutamate
Gene Name:
ARG7
Uniprot ID:
Q04728
Molecular weight:
47848.30078
Reactions
N(2)-acetyl-L-ornithine + L-glutamate → L-ornithine + N-acetyl-L-glutamate.
Acetyl-CoA + L-glutamate → CoA + N-acetyl-L-glutamate.
Protein Details
2. Amino-acid acetyltransferase, mitochondrial
General function:
Involved in arginine biosynthetic process
Specific function:
N-acetylglutamate synthase involved in arginine biosynthesis
Gene Name:
ARG2
Uniprot ID:
P40360
Molecular weight:
65609.5
Reactions
Acetyl-CoA + L-glutamate → CoA + N-acetyl-L-glutamate.
Protein Details
3. Protein ARG5,6, mitochondrial
General function:
Involved in acetylglutamate kinase activity
Specific function:
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH
Gene Name:
ARG5
Uniprot ID:
Q01217
Molecular weight:
94868.39844
Reactions
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate → N-acetyl-5-glutamyl phosphate + NADPH.
ATP + N-acetyl-L-glutamate → ADP + N-acetyl-L-glutamate 5-phosphate.