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 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
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.