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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 is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-glutamyl 5-phosphate exists in all living species, ranging from bacteria to humans.
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
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)-1.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.89 m³·mol⁻¹ChemAxon
Polarizability21.96 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 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
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.