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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:05 UTC
HMDB IDHMDB0001228
Secondary Accession Numbers
  • HMDB01228
Metabolite Identification
Common NameL-Glutamic acid 5-phosphate
DescriptionL-Glutamic acid 5-phosphate, also known as L-gamma-glutamyl-5-p or L-glutam-5-yl phosphate, 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. Outside of the human body, L-Glutamic acid 5-phosphate has been detected, but not quantified in, several different foods, such as hedge mustards, common beans, docks, common buckwheats, and horseradish tree. This could make L-glutamic acid 5-phosphate a potential biomarker for the consumption of these foods.
Structure
Data?1582752185
Synonyms
ValueSource
(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoic acidChEBI
5-oxo-5-(Phosphonooxy)-L-norvalineChEBI
L-Glutam-5-yl phosphateChEBI
L-Glutamate 5-phosphateChEBI
L-Glutamyl 5-phosphateChEBI
(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoateGenerator
L-Glutam-5-yl phosphoric acidGenerator
L-Glutamic acid 5-phosphoric acidGenerator
L-Glutamyl 5-phosphoric acidGenerator
L-gamma-Glutamyl-5-pHMDB
L-gamma-Glutamyl-5-phosphateHMDB
L-Glutamate-5-phosphateHMDB
L-Glutamyl-5-pHMDB
gamma-Glutamyl phosphateHMDB
Chemical FormulaC5H10NO7P
Average Molecular Weight227.1092
Monoisotopic Molecular Weight227.019488191
IUPAC Name(2S)-2-amino-5-oxo-5-(phosphonooxy)pentanoic acid
Traditional NameL-gamma-glutamyl phosphate
CAS Registry Number13254-53-0
SMILES
N[C@@H](CCC(=O)OP(O)(O)=O)C(O)=O
InChI Identifier
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
InChI KeyPJRXVIJAERNUIP-VKHMYHEASA-N
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-1f025e73303e86357c09Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9830000000-dfd0fdd7b5d37360baceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-4940000000-e0efc97dbf5f13f5b035Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9700000000-a154ebeef5e0f0f43204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b1be60027526c9bde31bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9040000000-9de98862247938227647Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-800f97e7da351e4f9a42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a620dcfe7b9e2908b2a5Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022500
KNApSAcK IDNot Available
Chemspider ID167893
KEGG Compound IDC03287
BioCyc IDNot Available
BiGG ID41564
Wikipedia LinkNot Available
METLIN ID6093
PubChem Compound193475
PDB IDNot Available
ChEBI ID17798
Food Biomarker OntologyNot Available
VMH IDGLU5P
References
Synthesis ReferenceJournal of Heterocyclic Chemistry (1987), 24(1), 279-82.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that converts glutamate to glutamate 5-semialdehyde, an intermediate in the biosynthesis of proline, ornithine and arginine.
Gene Name:
ALDH18A1
Uniprot ID:
P54886
Molecular weight:
87088.29
Reactions
Adenosine triphosphate + L-Glutamic acid → ADP + L-Glutamic acid 5-phosphatedetails
L-Glutamic gamma-semialdehyde + Phosphate + NADP → L-Glutamic acid 5-phosphate + NADPHdetails
Adenosine triphosphate + L-Glutamic acid → ADP + L-Glutamic acid 5-phosphatedetails
L-Glutamic gamma-semialdehyde + Phosphate + NADP → L-Glutamic acid 5-phosphate + NADPH + Hydrogen Iondetails