Record Information
Version2.0
Creation Date2012-05-31 13:48:00 -0600
Update Date2015-06-03 15:53:51 -0600
Secondary Accession Numbers
  • ECMDB01228
Identification
Name:L-Glutamic acid 5-phosphate
DescriptionL-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
Thumb
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.
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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility10.9 g/LALOGPS
logP-2ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area147.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.45 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
proline metabolismPW000794 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, Positivesplash10-0002-9100000000-1f025e73303e86357c09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9830000000-dfd0fdd7b5d37360baceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-4940000000-e0efc97dbf5f13f5b035View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9700000000-a154ebeef5e0f0f43204View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b1be60027526c9bde31bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9040000000-9de98862247938227647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-800f97e7da351e4f9a42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a620dcfe7b9e2908b2a5View in MoNA
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
External Links:
ResourceLink
CHEBI ID17798
HMDB IDHMDB01228
Pubchem Compound ID193475
Kegg IDC03287
ChemSpider ID167893
Wikipedia IDNot Available
BioCyc IDL-GLUTAMATE-5-P
EcoCyc IDL-GLUTAMATE-5-P

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH dependent reduction of L-gamma- glutamyl 5-phosphate into L-glutamate 5-semialdehyde and phosphate. The product spontaneously undergoes cyclization to form 1-pyrroline-5-carboxylate
Gene Name:
proA
Uniprot ID:
P07004
Molecular weight:
44630
Reactions
L-glutamate 5-semialdehyde + phosphate + NADP(+) = L-glutamyl 5-phosphate + NADPH.
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Catalyzes the transfer of a phosphate group to glutamate to form glutamate 5-phosphate which rapidly cyclizes to 5- oxoproline
Gene Name:
proB
Uniprot ID:
P0A7B5
Molecular weight:
39056
Reactions
ATP + L-glutamate = ADP + L-glutamate 5-phosphate.