N-Acetyl-L-glutamyl 5-phosphate (ECMDB06456) (M2MDB000672)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (818)
Record Information
Version2.0
Creation Date2012-05-31 14:08:27 -0600
Update Date2015-06-03 15:54:52 -0600
Secondary Accession Numbers
  • ECMDB06456
Identification
Name:N-Acetyl-L-glutamyl 5-phosphate
DescriptionN-Acetyl-L-glutamyl 5-phosphate is an intermediate in urea cycle and metabolism of amino groups. The enzyme N-acetyl-gamma-glutamyl-phosphate reductase [EC:1.2.1.38] catalyzes the conversion of this metabolite into N-acetyl-L-glutamate 5-semialdehyde. This reaction is irreversible and occurs in the cytoplasm (BiGG database)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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-glutamyl-P
  • N-acetyl-L-glutamate-5-phosphate
  • N-acetylglutamyl-P
  • N-Acetyl-5-glutamyl phosphate
  • n-Acetyl-5-glutamyl phosphoric acid
  • N-Acetyl-5-glutamyl phosphoric acid
  • N-Acetyl-5-oxo-5-(phosphonooxy)-L-norvaline
  • N-Acetyl-g-L-glutamyl phosphate
  • N-Acetyl-g-L-glutamyl phosphoric acid
  • N-Acetyl-gamma-L-glutamyl phosphate
  • N-Acetyl-gamma-L-glutamyl phosphoric acid
  • N-Acetyl-glutamyl-P
  • N-Acetyl-L-glutamate 5-phosphate
  • N-Acetyl-L-glutamate-5-phosphate
  • N-Acetyl-L-glutamic acid 5-phosphate
  • N-Acetyl-L-glutamic acid 5-phosphoric acid
  • n-Acetyl-L-glutamic acid-5-phosphoric acid
  • N-Acetyl-L-glutamic acid-5-phosphoric acid
  • N-Acetyl-L-glutamyl 5-phosphate
  • N-Acetyl-L-glutamyl 5-phosphoric acid
  • N-Acetyl-γ-L-glutamyl phosphate
  • N-Acetyl-γ-L-glutamyl phosphoric acid
  • N-Acetylglutamyl-P
  • N-AcGlu-P
Chemical Formula:C7H12NO8P
Weight:Average: 269.1458
Monoisotopic: 269.030052877
InChI Key:FCVIHFVSXHOPSW-YFKPBYRVSA-N
InChI:InChI=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
CAS number:15383-57-0
IUPAC Name:(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
Traditional IUPAC Name:(2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid
SMILES:CC(=O)N[C@@H](CCC(=O)OP(O)(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
  • 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
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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:Cytoplasm
Reactions:
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
Adenosine triphosphate + N-Acetyl-L-alanine <> ADP + N-Acetyl-L-glutamyl 5-phosphate
<i>N</i>-acetyl-L-glutamate + Adenosine triphosphate > N-Acetyl-L-glutamyl 5-phosphate + ADP
Adenosine triphosphate + N-acetyl-L-glutamate > ADP + N-Acetyl-L-glutamyl 5-phosphate
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH
N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADP
N-Acetyl-L-glutamyl 5-phosphate + NADPH + Hydrogen ion + NADPH > N-acetyl-L-glutamate + Phosphate + NADP
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP
SMPDB Pathways:
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
ornithine metabolismPW000791 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9010000000-b0a55da1a5a5b19cb1d4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9010000000-42bde2dc702d9b13da76View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9050000000-71b3eb12e2ae4f419455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-eb5a9659d9563f71cfedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9428bc78f2587e624b2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9010000000-fdf484605ec8efcf1973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5c2f91e14126fc9d0952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7084495cb0b628b5da4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fka-3690000000-1006721922db38442ba6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-4930000000-eb999b44d4988128c1c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9500000000-78a70933fe87b25941adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0090000000-041c62aaf9a011fbf28aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-2930000000-e4bd8858ef8860dc9111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0035-9400000000-2015735feb749a5b240bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16878
HMDB IDHMDB06456
Pubchem Compound ID440236
Kegg IDC04133
ChemSpider ID389220
Wikipedia IDNot Available
BioCyc IDN-ACETYL-GLUTAMYL-P
EcoCyc IDN-ACETYL-GLUTAMYL-P
Ligand ExpoX2W

Enzymes

Protein Details
1. Acetylglutamate kinase
General function:
Involved in acetylglutamate kinase activity
Specific function:
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L- glutamate 5-phosphate
Gene Name:
argB
Uniprot ID:
P0A6C8
Molecular weight:
27159
Reactions
ATP + N-acetyl-L-glutamate = ADP + N-acetyl-L-glutamate 5-phosphate.
Protein Details
2. N-acetyl-gamma-glutamyl-phosphate reductase
General function:
Involved in N-acetyl-gamma-glutamyl-phosphate reductase activity
Specific function:
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH
Gene Name:
argC
Uniprot ID:
P11446
Molecular weight:
35952
Reactions
N-acetyl-L-glutamate 5-semialdehyde + NADP(+) + phosphate = N-acetyl-5-glutamyl phosphate + NADPH.