L-Aspartyl-4-phosphate (ECMDB12250) (M2MDB000834)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (1029)
Record Information
Version2.0
Creation Date2012-05-31 14:21:21 -0600
Update Date2015-06-03 17:19:04 -0600
Secondary Accession Numbers
  • ECMDB12250
Identification
Name:L-Aspartyl-4-phosphate
DescriptionL-Aspartyl-4-phosphate is involved in both the lysine biosynthesis and homoserine biosynthesis pathways.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 4-Phospho-L-aspartate
  • 4-Phospho-L-aspartic acid
  • Asp-P
  • L-β-aspartyl-P
  • L-β-aspartyl-phosphate
  • L-β-aspartyl-phosphoric acid
  • L-4-Aspartyl phosphate
  • L-4-Aspartyl phosphoric acid
  • L-Aspartate b-semialdehyde
  • L-Aspartate beta-semialdehyde
  • L-Aspartate β-semialdehyde
  • L-Aspartic acid b-semialdehyde
  • L-Aspartic acid beta-semialdehyde
  • L-Aspartic acid β-semialdehyde
  • L-aspartyl-β-phosphate
  • L-Aspartyl-β-phosphoric acid
  • L-aspartyl-4-P
  • L-Aspartyl-4-phosphoric acid
  • L-aspartyl-b-phosphate
  • L-Aspartyl-b-phosphoric acid
  • L-Aspartyl-beta-phosphate
  • L-Aspartyl-beta-phosphoric acid
  • L-Aspartyl-β-phosphate
  • L-Aspartyl-β-phosphoric acid
  • L-b-aspartyl-P
  • L-b-aspartyl-phosphate
  • L-b-Aspartyl-phosphoric acid
  • L-beta-Aspartyl-P
  • L-beta-Aspartyl-phosphate
  • L-beta-Aspartyl-phosphoric acid
  • L-β-Aspartyl-P
  • L-β-Aspartyl-phosphate
  • L-β-Aspartyl-phosphoric acid
Chemical Formula:C4H8NO7P
Weight:Average: 213.0826
Monoisotopic: 213.003838127
InChI Key:IXZNKTPIYKDIGG-UHFFFAOYSA-N
InChI:InChI=1S/C4H8NO7P/c5-2(4(7)8)1-3(6)12-13(9,10)11/h2H,1,5H2,(H,7,8)(H2,9,10,11)
CAS number:22138-53-0
IUPAC Name:2-amino-4-oxo-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name:aspartyl phosphate
SMILES:NC(CC(=O)OP(O)(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic 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 ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • Acyl monophosphate
  • Acyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Fatty acid
  • Carboxylic acid salt
  • Amino acid
  • Carboxylic acid
  • Organic salt
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area147.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.69 m³·mol⁻¹ChemAxon
Polarizability16.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-4-phosphate + ADP
L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH
L-Aspartic acid + Adenosine triphosphate > L-Aspartyl-4-phosphate + ADP
L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > Adenosine diphosphate + L-Aspartyl-4-phosphate + ADP
L-Aspartyl-4-phosphate + NADPH + Hydrogen ion + NADPH > Phosphate + NADP + L-Aspartate-semialdehyde
L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-4-phosphate + ADP
L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: threonine biosynthesis from aspartatePW000976 ThumbThumb?image type=greyscaleThumb?image type=simple
threonine biosynthesisPW000817 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, Positivesplash10-0002-9100000000-9a4ebec80a996ceb6040View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9510000000-fa31ef1b6e354291d94fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-4910000000-7a0e522ac0bb6aada3aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9400000000-090a883ab8d4353e4af2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2a76e0c5095038de7b5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9220000000-92fa110ca2d5693f4ec6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e85bd4bcd5e9577442b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2fb9c2e1a0877c05b10eView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB12250
Pubchem Compound ID832
Kegg IDC03082
ChemSpider ID809
Wikipedia IDNot Available
BioCyc IDL-BETA-ASPARTYL-P
EcoCyc IDL-BETA-ASPARTYL-P

Enzymes

Protein Details
1. Bifunctional aspartokinase/homoserine dehydrogenase 1
General function:
Involved in amino acid binding
Specific function:
L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:
thrA
Uniprot ID:
P00561
Molecular weight:
89119
Reactions
L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.
Protein Details
2. Bifunctional aspartokinase/homoserine dehydrogenase 2
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:
metL
Uniprot ID:
P00562
Molecular weight:
88887
Reactions
L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.
Protein Details
3. Lysine-sensitive aspartokinase 3
General function:
Involved in amino acid binding
Specific function:
ATP + L-aspartate = ADP + 4-phospho-L- aspartate
Gene Name:
lysC
Uniprot ID:
P08660
Molecular weight:
48531
Reactions
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.
Protein Details
4. Aspartate-semialdehyde dehydrogenase
General function:
Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH
Gene Name:
asd
Uniprot ID:
P0A9Q9
Molecular weight:
40018
Reactions
L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH.