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Record Information
Version	2.0
Creation Date	2012-05-31 14:09:27 -0600
Update Date	2015-06-03 15:54:54 -0600
Secondary Accession Numbers	ECMDB06802
Identification
Name:	O-Phospho-4-hydroxy-L-threonine
Description	O-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6ceffbc> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	L-alpha-amino acids
Alternative Parents	Short-chain hydroxy acids and derivatives Monoalkyl phosphates Beta hydroxy acids and derivatives Fatty acids and conjugates Secondary alcohols Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	L-threonine derivative (CHEBI:18336 ) O-phosphoamino acid (CHEBI:18336 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 22.7 g/L ALOGPS logP -2.4 ALOGPS logP -3.9 ChemAxon logS -0.98 ALOGPS pKa (Strongest Acidic) 1.31 ChemAxon pKa (Strongest Basic) 8.93 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 150.31 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 38.88 m³·mol⁻¹ ChemAxon Polarizability 16.6 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 1430936196 PW000891
KEGG Pathways:	Glycine, serine and threonine metabolism ec00260 Metabolic pathways eco01100 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Vitamin B6 metabolism ec00750
EcoCyc Pathways:	pyridoxal 5'-phosphate biosynthesis I PYRIDOXSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9200000000-a8f91387710592709ff8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-01ow-9711000000-89a880807057686a60b1 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00r2-2920000000-c23edaafe01dd32ccd6a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-9600000000-fd8c6ec273c259b6d693 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-9300000000-42e18773c2868e50da83 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03mj-9850000000-0cd651cd24395dbae4a1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9100000000-a925d7c6b56522b6d34b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-5c41cf86b2bcca517868 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-2590000000-a9146bba129194b49abb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-9200000000-e8dbc889a8d9573cd396 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001j-9000000000-9eec4757ad69989237c0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01ta-9030000000-a684f48886db0724b48e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-177256aadc387d9ad236 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 18336 HMDB ID HMDB06802 Pubchem Compound ID 440901 Kegg ID C06055 ChemSpider ID 389731 Wikipedia ID Not Available BioCyc ID 4-PHOSPHONOOXY-THREONINE EcoCyc ID 4-PHOSPHONOOXY-THREONINE Ligand Expo 4TP

Enzymes