ECMDB: O-Phospho-4-hydroxy-L-threonine (ECMDB06802) (M2MDB000691)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (1082)

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

MOL SDF PDB SMILES InChI

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

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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.88 m³·mol⁻¹	ChemAxon
Polarizability	16.6 Å³	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:

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

Protein Details

1. Threonine synthase

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.

Protein Details

2. Pyridoxine 5'-phosphate synthase

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.

Protein Details

3. 4-hydroxythreonine-4-phosphate dehydrogenase

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.

Protein Details

4. Phosphoserine aminotransferase

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.

O-Phospho-4-hydroxy-L-threonine (ECMDB06802) (M2MDB000691)

Structure for #<Compound:0xab827480>

Enzymes

Reactions

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Reactions

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