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Identification
YMDB IDYMDB00047
NameN-Acetyl-L-glutamyl 5-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-Acetyl-L-glutamyl 5-phosphate, also known as N-acetyl-5-glutamyl phosphoric acid, 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-glutamyl 5-phosphate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on N-Acetyl-L-glutamyl 5-phosphate.
Structure
Thumb
Synonyms
  • (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoate
  • (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
  • N-acetyl-5-glutamyl phosphate
  • N-Acetyl-5-glutamyl phosphoric acid
  • N-acetyl-5-oxo-5-(phosphonooxy)-L-norvaline
  • N-acetyl-gamma-l-glutamyl phosphate
  • N-acetyl-L-glutamate 5-phosphate
  • N-Acetyl-L-glutamic acid 5-phosphoric acid
  • N-Acetyl-L-glutamyl 5-phosphoric acid
  • N-Acetyl-gamma-glutamyl phosphate
  • N-Acetyl-γ-glutamyl phosphate
CAS number15383-57-0
WeightAverage: 269.1458
Monoisotopic: 269.030052877
InChI KeyFCVIHFVSXHOPSW-YFKPBYRVSA-N
InChIInChI=1S/C7H12NO8P/c1-4(9)8-5(7(11)12)2-3-6(10)16-17(13,14)15/h5H,2-3H2,1H3,(H,8,9)(H,11,12)(H2,13,14,15)/t5-/m0/s1
IUPAC Name(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
Traditional IUPAC Name(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
Chemical FormulaC7H12NO8P
SMILES[H]OC(=O)[C@@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C(=O)OP(=O)(O[H])O[H]
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
  • N-acyl-l-alpha-amino acid
  • Acyl monophosphate
  • Acyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Fatty acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxylic acid salt
  • Carboxamide group
  • Carboxylic acid
  • Carbonyl group
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP-1.9ALOGPS
logP-1.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.89 m³·mol⁻¹ChemAxon
Polarizability21.95 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
N-Acetyl-L-glutamyl 5-phosphate + NADPH + hydronNADP + phosphate + 2-Acetamido-5-oxopentanoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9010000000-b0a55da1a5a5b19cb1d4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9010000000-42bde2dc702d9b13da76JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fka-3690000000-1006721922db38442ba6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-4930000000-eb999b44d4988128c1c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9500000000-78a70933fe87b25941adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9050000000-71b3eb12e2ae4f419455JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-eb5a9659d9563f71cfedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9428bc78f2587e624b2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9010000000-fdf484605ec8efcf1973JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5c2f91e14126fc9d0952JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7084495cb0b628b5da4aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0090000000-041c62aaf9a011fbf28aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-2930000000-e4bd8858ef8860dc9111JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0035-9400000000-2015735feb749a5b240bJSpectraViewer
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
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
  • Jauniaux, J. C., Urrestarazu, L. A., Wiame, J. M. (1978). "Arginine metabolism in Saccharomyces cerevisiae: subcellular localization of the enzymes." J Bacteriol 133:1096-1107.205532
  • 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
Synthesis Reference:Kuramitsu, Shigenori; Masui, Ryoji. Cloning of thermostable acetylglutamate kinase gene from Sulfolobus tokodaii and use for N-acetyl-L-glutamate-5-phosphate biosynthesis. Jpn. Kokai Tokkyo Koho (2004), 12 pp. CODEN: JKXXAF JP 2004298187 A 2
External Links:
ResourceLink
CHEBI ID16878
HMDB IDHMDB06456
Pubchem Compound ID440236
Kegg IDC04133
ChemSpider ID389220
FOODB IDFDB023917
Wikipedia IDNot Available
BioCyc IDN-ACETYL-GLUTAMYL-P

Enzymes

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.