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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:27 -0600
Update Date	2015-06-03 15:54:52 -0600
Secondary Accession Numbers	ECMDB06456
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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa12d5194> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Glutamic acid and derivatives
Alternative Parents	N-acyl-L-alpha-amino acids Acyl monophosphates Fatty acids and conjugates Dicarboxylic acids and derivatives Acetamides Secondary carboxylic acid amides Carboxylic acid salts Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	L-glutamic acid derivative (CHEBI:16878 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.64 g/L ALOGPS logP -1.9 ALOGPS logP -1.8 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 1.23 ChemAxon pKa (Strongest Basic) -1.8 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 150.23 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 51.89 m³·mol⁻¹ ChemAxon Polarizability 21.95 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 metabolism PW000790 ornithine metabolism PW000791
KEGG Pathways:	Arginine and proline metabolism ec00330 Metabolic pathways eco01100
EcoCyc Pathways:	ornithine biosynthesis GLUTORN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9010000000-b0a55da1a5a5b19cb1d4 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-006t-9010000000-42bde2dc702d9b13da76 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fka-3690000000-1006721922db38442ba6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-007k-4930000000-eb999b44d4988128c1c9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-9500000000-78a70933fe87b25941ad View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9050000000-71b3eb12e2ae4f419455 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-eb5a9659d9563f71cfed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-9428bc78f2587e624b2e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9010000000-fdf484605ec8efcf1973 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-5c2f91e14126fc9d0952 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-7084495cb0b628b5da4a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00b9-0090000000-041c62aaf9a011fbf28a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-003r-2930000000-e4bd8858ef8860dc9111 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0035-9400000000-2015735feb749a5b240b View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 16878 HMDB ID HMDB06456 Pubchem Compound ID 440236 Kegg ID C04133 ChemSpider ID 389220 Wikipedia ID Not Available BioCyc ID N-ACETYL-GLUTAMYL-P EcoCyc ID N-ACETYL-GLUTAMYL-P Ligand Expo X2W

Enzymes