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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:03 UTC
HMDB IDHMDB01228
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Glutamic acid 5-phosphate
DescriptionL-Glutamic acid 5-phosphate is an intermediate in the urea cycle and the metabolism of amino groups. It is a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)In citrulline biosynthesis, it is a substrate of the enzyme glutamate-5-semialdehyde dehydrogenase [EC 1.2.1.41] and in proline synthesis it is a substrate of the enzyme Glutamate 5-kinase [EC 2.7.2.11] (BioCyc).
Structure
Thumb
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
(2S)-2-amino-5-oxo-5-PhosphonooxypentanoateGenerator
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
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 KeyInChIKey=PJRXVIJAERNUIP-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.45 m3·mol-1ChemAxon
Polarizability18.09 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022500
KNApSAcK IDNot Available
Chemspider ID167893
KEGG Compound IDC03287
BioCyc IDL-GLUTAMATE-5-P
BiGG ID41564
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01228
Metagene LinkHMDB01228
METLIN ID6093
PubChem Compound193475
PDB IDNot Available
ChEBI ID17798
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 + Phosphoric acid + NADP → L-Glutamic acid 5-phosphate + NADPHdetails
Adenosine triphosphate + L-Glutamic acid → ADP + L-Glutamic acid 5-phosphatedetails
L-Glutamic gamma-semialdehyde + Phosphoric acid + NADP → L-Glutamic acid 5-phosphate + NADPH + Hydrogen Iondetails