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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 is a very strong basic compound (based on its pKa). L-Glutamic acid 5-phosphate exists in all living species, ranging from bacteria to humans. L-glutamic acid 5-phosphate can be converted into L-glutamic gamma-semialdehyde through its interaction with the enzyme glutamate-5-semialdehyde dehydrogenase. In yeast, L-glutamic acid 5-phosphate is involved in the metabolic pathway called the proline metabolism pathway.
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
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 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
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.