P. aeruginosa Metabolome Database: O-Phospho-4-hydroxy-L-threonine (PAMDB000691)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000691

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 View Structure

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

Average Molecular Weight:

215.0985

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
Monoalkyl phosphate
Short-chain hydroxy acid
Beta-hydroxy acid
Amino fatty acid
Fatty acyl
Fatty acid
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

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 mg/mL	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:

Pathways:

Glycine, serine and threonine metabolism pae00260
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Vitamin B6 metabolism pae00750

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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

O-Phospho-4-hydroxy-L-threonine (PAMDB000691)

Structure for O-Phospho-4-hydroxy-L-threonine (PAMDB000691)