N-Acetyl-L-glutamyl 5-phosphate (PAMDB000672)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000672
Identification
Name: N-Acetyl-L-glutamyl 5-phosphate
Description:N-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
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🔍MOLSDFPDBSMILESInChIView 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
Average Molecular Weight: 269.1458
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-l-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.64 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.89 m3·mol-1ChemAxon
Polarizability21.96 Å3ChemAxon
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
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
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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, 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
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