Record Information
Version2.0
Creation Date2012-05-31 14:09:27 -0600
Update Date2015-06-03 15:54:54 -0600
Secondary Accession Numbers
  • ECMDB06802
Identification
Name:O-Phospho-4-hydroxy-L-threonine
DescriptionO-Phospho-4-hydroxy-L-threonine is involved in the vitamin B6 metabolism system. O-Phospho-4-hydroxy-L-threonine is a precursor for pyridoxine. O-Phospho-4-hydroxy-L-threonine can be converted to 4-hydroxy-L-threonine and 2-Amino-3-oxo-4-phosphonooxybutyrate by threonine synthase [EC:4.2.3.1] and 4-hydroxythreonine-4-phosphate dehydrogenase [EC:1.1.1.262], respectively.
Structure
Thumb
Synonyms:
  • 4-(Phosphonooxy)-L-threonine
  • 4-(Phosphonooxy)-threonine
  • 4-Phospho-hydroxy-threonine
  • 4-Phosphonooxy-L-threonine
  • O-phospho-4-hydroxy-L-threonine
  • L-Threo-3-hydroxy-homoserine phosphate
  • L-threo-3-Hydroxy-homoserine phosphoric acid
  • O-Phospho-4-hydroxy-L-threonine
  • Phospho-hydroxy-threonine
Chemical Formula:C4H10NO7P
Weight:Average: 215.0985
Monoisotopic: 215.019488191
InChI Key:FKHAKIJOKDGEII-GBXIJSLDSA-N
InChI:InChI=1S/C4H10NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h2-3,6H,1,5H2,(H,7,8)(H2,9,10,11)/t2-,3+/m1/s1
CAS number:Not Available
IUPAC Name:(2S,3S)-2-amino-3-hydroxy-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name:4-(phosphonooxy)-L-threonine
SMILES:N[C@@H]([C@H](O)COP(O)(O)=O)C(O)=O
Chemical Taxonomy
Description 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
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Monoalkyl phosphate
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility22.7 g/LALOGPS
logP-2.4ALOGPS
logP-3.9ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)8.93ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area150.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.88 m³·mol⁻¹ChemAxon
Polarizability16.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
1-Deoxy-D-xylulose 5-phosphate + NAD + O-Phospho-4-hydroxy-L-threonine > Carbon dioxide + Hydrogen ion +2 Water + NADH + Pyridoxine 5'-phosphate + Phosphate
Water + O-Phospho-4-hydroxy-L-threonine > 4-Hydroxy-L-threonine + Phosphate
L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
O-Phospho-4-hydroxy-L-threonine + alpha-Ketoglutarate <> 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate
O-Phospho-4-hydroxy-L-threonine + Water <> 4-Hydroxy-L-threonine + Phosphate
O-Phospho-4-hydroxy-L-threonine + NAD <> 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
O-Phospho-4-hydroxy-L-threonine + NAD > Hydrogen ion + NADH + 2-Amino-3-oxo-4-phosphonooxybutyrate
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
4-Hydroxy-L-threonine + Adenosine triphosphate > Hydrogen ion + O-Phospho-4-hydroxy-L-threonine + ADP
O-Phospho-4-hydroxy-L-threonine + NAD > 2-Amino-3-phosphonopropionic acid + Carbon dioxide + NADH
O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate
Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
NAD + 2-Amino-3-oxo-4-phosphonooxybutyrate + O-Phospho-4-hydroxy-L-threonine <> 3-Amino-2-oxopropyl phosphate + Carbon dioxide + NADH + Hydrogen ion
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> A-Ketoglutaric acid oxime + O-Phospho-4-hydroxy-L-threonine
L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine
L-Glutamic acid + L-Glutamate <> Oxoglutaric acid + O-Phospho-4-hydroxy-L-threonine
L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + A-Ketoglutaric acid oxime
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
O-Phospho-4-hydroxy-L-threonine + NAD <>2 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
L-Glutamate + 2 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
O-Phospho-4-hydroxy-L-threonine + NAD <>2 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
SMPDB Pathways:
Vitamin B6 1430936196PW000891 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, Positivesplash10-0002-9200000000-a8f91387710592709ff8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ow-9711000000-89a880807057686a60b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-2920000000-c23edaafe01dd32ccd6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9600000000-fd8c6ec273c259b6d693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9300000000-42e18773c2868e50da83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mj-9850000000-0cd651cd24395dbae4a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-a925d7c6b56522b6d34bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c41cf86b2bcca517868View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2590000000-a9146bba129194b49abbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-e8dbc889a8d9573cd396View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9000000000-9eec4757ad69989237c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ta-9030000000-a684f48886db0724b48eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-177256aadc387d9ad236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18336
HMDB IDHMDB06802
Pubchem Compound ID440901
Kegg IDC06055
ChemSpider ID389731
Wikipedia IDNot Available
BioCyc ID4-PHOSPHONOOXY-THREONINE
EcoCyc ID4-PHOSPHONOOXY-THREONINE
Ligand Expo4TP

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the gamma-elimination of phosphate from L- phosphohomoserine and the beta-addition of water to produce L- threonine. To a lesser extent, is able to slowly catalyze the deamination of L-threonine into alpha-ketobutyrate and that of L- serine and 3-chloroalanine into pyruvate. Is also able to rapidly convert vinylglycine to threonine, which proves that the pyridoxal p-quinonoid of vinylglycine is an intermediate in the TS reaction
Gene Name:
thrC
Uniprot ID:
P00934
Molecular weight:
47113
Reactions
O-phospho-L-homoserine + H(2)O = L-threonine + phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the complicated ring closure reaction between the two acyclic compounds 1-deoxy-D-xylulose-5-phosphate (DXP) and 3-amino-2-oxopropyl phosphate (1-amino-acetone-3-phosphate or AAP) to form pyridoxine 5'-phosphate (PNP) and inorganic phosphate
Gene Name:
pdxJ
Uniprot ID:
P0A794
Molecular weight:
26384
Reactions
1-deoxy-D-xylulose 5-phosphate + 3-amino-2-oxopropyl phosphate = pyridoxine 5'-phosphate + phosphate + 2 H(2)O.
General function:
Involved in 4-hydroxythreonine-4-phosphate dehydrogenase activity
Specific function:
Catalyzes the NAD(P)-dependent oxidation of 4- (phosphohydroxy)-L-threonine (HTP) into 2-amino-3-oxo-4- (phosphohydroxy)butyric acid which spontaneously decarboxylates to form 3-amino-2-oxopropyl phosphate (AHAP)
Gene Name:
pdxA
Uniprot ID:
P19624
Molecular weight:
35114
Reactions
4-(phosphonooxy)-L-threonine + NAD(+) = (2S)-2-amino-3-oxo-4-phosphonooxybutanoate + NADH.
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Uniprot ID:
P23721
Molecular weight:
39783
Reactions
O-phospho-L-serine + 2-oxoglutarate = 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.