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Record Information
Version	2.0
Creation Date	2012-05-31 13:48:00 -0600
Update Date	2015-06-03 15:53:51 -0600
Secondary Accession Numbers	ECMDB01228
Identification
Name:	L-Glutamic acid 5-phosphate
Description	L-Glutamic acid 5-phosphate is an intermediate in the urea cycle and metabolism of amino groups, a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xace91ce8> Close
Synonyms:	Glu-5-P L-γ-glutamyl-5-P L-γ-glutamyl-5-phosphate L-γ-glutamyl-5-phosphoric acid L-g-Glutamyl-5-P L-g-Glutamyl-5-phosphate L-g-Glutamyl-5-phosphoric acid L-gamma-Glutamyl-5-P L-gamma-Glutamyl-5-phosphate L-gamma-Glutamyl-5-phosphoric acid L-Glutamate 5-phosphate L-Glutamate-5-phosphate L-Glutamic acid 5-phosphate L-Glutamic acid 5-phosphoric acid L-Glutamic acid-5-phosphoric acid L-Glutamyl 5-phosphate L-Glutamyl 5-phosphoric acid L-Glutamyl-5-P L-Glutamyl-5-phosphate L-Glutamyl-5-phosphoric acid L-γ-Glutamyl-5-P L-γ-Glutamyl-5-phosphate L-γ-Glutamyl-5-phosphoric acid
Chemical Formula:	C5H10NO7P
Weight:	Average: 227.1092 Monoisotopic: 227.019488191
InChI Key:	PJRXVIJAERNUIP-VKHMYHEASA-N
InChI:	InChI=1S/C5H10NO7P/c6-3(5(8)9)1-2-4(7)13-14(10,11)12/h3H,1-2,6H2,(H,8,9)(H2,10,11,12)/t3-/m0/s1
CAS number:	13254-53-0
IUPAC Name:	(2S)-2-amino-5-oxo-5-(phosphonooxy)pentanoic acid
Traditional IUPAC Name:	L-gamma-glutamyl phosphate
SMILES:	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	L-alpha-amino acids Acyl monophosphates Fatty acids and conjugates Dicarboxylic acids and derivatives Carboxylic acid salts Amino acids Carboxylic acids Organopnictogen compounds Organic salts Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Glutamic acid or derivatives Alpha-amino acid L-alpha-amino acid Acyl monophosphate Acyl phosphate Dicarboxylic acid or derivatives Organic phosphoric acid derivative Fatty acid Carboxylic acid salt Amino acid Carboxylic acid Primary amine Organooxygen compound Organonitrogen compound Hydrocarbon derivative Primary aliphatic amine Organic oxide Organic nitrogen compound Organopnictogen compound Carbonyl group Amine Organic oxygen compound Organic salt Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	gamma-glutamyl phosphate (CHEBI:17798 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 10.9 g/L ALOGPS logP -2 ALOGPS logP -3 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 1.12 ChemAxon pKa (Strongest Basic) 9.51 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 147.15 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 42.45 m³·mol⁻¹ ChemAxon Polarizability 18.09 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:	Adenosine triphosphate + L-Glutamate > ADP + L-Glutamic acid 5-phosphate L-Glutamic acid 5-phosphate + Hydrogen ion + NADPH > L-Glutamic-gamma-semialdehyde + NADP + Phosphate Adenosine triphosphate + L-Glutamate <> ADP + L-Glutamyl 5-phosphate + L-Glutamic acid 5-phosphate L-Glutamic-gamma-semialdehyde + Phosphate + NADP <> L-Glutamyl 5-phosphate + NADPH + Hydrogen ion + L-Glutamic acid 5-phosphate L-Glutamic-gamma-semialdehyde + Phosphate + NADP < L-Glutamic acid 5-phosphate + NADPH + Hydrogen ion L-Glutamic-gamma-semialdehyde + Inorganic phosphate + NADP > L-Glutamic acid 5-phosphate + NADPH L-Glutamic acid 5-phosphate + Hydrogen ion + NADPH + NADPH > L-Glutamic-gamma-semialdehyde + NADP + Phosphate L-Glutamic-gamma-semialdehyde + Phosphate + NADP <> L-Glutamic acid 5-phosphate + NADPH + Hydrogen ion Adenosine triphosphate + L-Glutamate <> ADP + L-Glutamic acid 5-phosphate L-Glutamic-gamma-semialdehyde + Phosphate + NADP <> L-Glutamic acid 5-phosphate + NADPH + Hydrogen ion Adenosine triphosphate + L-Glutamate <> ADP + L-Glutamic acid 5-phosphate
SMPDB Pathways:	proline metabolism PW000794
KEGG Pathways:	Arginine and proline metabolism ec00330 Metabolic pathways eco01100
EcoCyc Pathways:	proline biosynthesis I PROSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9100000000-1f025e73303e86357c09 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-0fk9-9830000000-dfd0fdd7b5d37360bace View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer 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 splash10-01qa-4940000000-e0efc97dbf5f13f5b035 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9700000000-a154ebeef5e0f0f43204 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9100000000-b1be60027526c9bde31b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9040000000-9de98862247938227647 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-800f97e7da351e4f9a42 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a620dcfe7b9e2908b2a5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-9010000000-fd2b2036f447f482b04a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-3970000000-225c75caa9353c31ca4c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9100000000-5acb01b87dc2c83bc22f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a59-9000000000-a92b4200472a0a756a42 View in MoNA 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 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17798 HMDB ID HMDB01228 Pubchem Compound ID 193475 Kegg ID C03287 ChemSpider ID 167893 Wikipedia ID Not Available BioCyc ID L-GLUTAMATE-5-P EcoCyc ID L-GLUTAMATE-5-P

Enzymes