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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
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 acidN-Acetyl-L-glutamyl 5-phosphate + ADP
Acetyl-CoA + L-Glutamic acidN-acetyl-L-glutamic acid + hydron + Coenzyme A
L-Glutamic acid + N-AcetylornithineN-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
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
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
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

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.
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.
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.