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Identification
YMDB IDYMDB00233
NameL-Glutamic acid 5-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Glutamic acid 5-phosphate, also known as L-glutam-5-yl phosphate or L-glutamyl 5-phosphoric acid, 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. L-Glutamic acid 5-phosphate exists in all living species, ranging from bacteria to plants to humans. In yeast, L-glutamic acid 5-phosphate is involved in the metabolic pathway called the proline metabolism pathway. Based on a literature review very few articles have been published on L-Glutamic acid 5-phosphate.
Structure
Thumb
Synonyms
  • L-gamma-glutamyl-5-P
  • L-gamma-glutamyl-5-phosphate
  • L-Glutamate 5-phosphate
  • L-glutamate-5-phosphate
  • L-Glutamic acid 5-phosphate
  • L-Glutamic acid 5-phosphic acid
  • L-glutamyl 5-phosphate
  • L-glutamyl-5-P
  • (2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoic acid
  • 5-oxo-5-(Phosphonooxy)-L-norvaline
  • L-Glutam-5-yl phosphate
  • (2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoate
  • L-Glutam-5-yl phosphoric acid
  • L-Glutamic acid 5-phosphoric acid
  • L-Glutamyl 5-phosphoric acid
  • gamma-Glutamyl phosphate
  • γ-Glutamyl phosphate
CAS number13254-53-0
WeightAverage: 227.1092
Monoisotopic: 227.019488191
InChI KeyPJRXVIJAERNUIP-VKHMYHEASA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-5-oxo-5-(phosphonooxy)pentanoic acid
Traditional IUPAC NameL-gamma-glutamyl phosphate
Chemical FormulaC5H10NO7P
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])C(=O)OP(=O)(O[H])O[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB Pathways
Proline MetabolismPW002365 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB Reactions
L-Glutamic acid 5-phosphate + hydron + NADPHl-Glutamic-gamma-semialdehyde + NADP + phosphate
KEGG Reactions
Adenosine triphosphate + L-Glutamic acidL-Glutamic acid 5-phosphate + ADP
L-Glutamic acid 5-phosphate + NADPH + hydronNADP + phosphate + l-Glutamic-gamma-semialdehyde
NADH + L-Glutamic acid 5-phosphate + hydronNAD + phosphate + l-Glutamic-gamma-semialdehyde
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-1f025e73303e86357c09JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9830000000-dfd0fdd7b5d37360baceJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-4940000000-e0efc97dbf5f13f5b035JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9700000000-a154ebeef5e0f0f43204JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b1be60027526c9bde31bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9040000000-9de98862247938227647JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-800f97e7da351e4f9a42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a620dcfe7b9e2908b2a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9010000000-fd2b2036f447f482b04aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3970000000-225c75caa9353c31ca4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-5acb01b87dc2c83bc22fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9000000000-a92b4200472a0a756a42JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.
External Links:
ResourceLink
CHEBI ID17798
HMDB IDHMDB01228
Pubchem Compound ID193475
Kegg IDC03287
ChemSpider ID167893
FOODB IDFDB022500
Wikipedia IDNot Available
BioCyc IDL-GLUTAMATE-5-P

Enzymes

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:
PRO1
Uniprot ID:
P32264
Molecular weight:
47161.69922
Reactions
ATP + L-glutamate → ADP + L-glutamate 5-phosphate.
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:
PRO2
Uniprot ID:
P54885
Molecular weight:
49740.0
Reactions
L-glutamate 5-semialdehyde + phosphate + NADP(+) → L-glutamyl 5-phosphate + NADPH.