P. aeruginosa Metabolome Database: L-Threonine O-3-phosphate (PAMDB001646)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001646

Identification

Name:

L-Threonine O-3-phosphate

Description:

In Pseudomonas aeruginosa, acid phosphatase / phosphotransferase and alkaline phosphatase are the enzymes that catalyze the chemical reaction L-threonine 3-O-phosphate[periplasmic space] + H2O[periplasmic space] -> L-threonine[periplasmic space] + phosphate[periplasmic space], where L-Threonine O-3-phosphate is a substrate (EcoCyc compound: L-THREONINE-O-3-PHOSPHATE).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2S,3R)-2-amino-3-hydroxybutanoate
(2S,3R)-2-amino-3-hydroxybutanoate 3-phosphate
(2S,3R)-2-amino-3-hydroxybutanoic acid
(2S,3R)-2-amino-3-hydroxybutanoic acid 3-phosphate
(2S,3R)-2-amino-3-Hydroxybutanoic acid 3-phosphoric acid
L-Threonine O-3-phosphate
L-Threonine O-3-phosphoric acid
L-Threonine O-phosphate
L-Threonine O-phosphoric acid
L-Threonine phosphate
L-Threonine phosphoric acid
O-Phospho-L-threonine
O-Phosphono-L-threonine
O3-phosphothreonine
Phospho-L-threonine
Phosphothreonine
Synonyms Sources
Threonine phosphate ester
Threonine phosphoric acid ester
Threoninium dihydrogen phosphate
Threoninium dihydrogen phosphoric acid

Chemical Formula:

C₄H₁₀NO₆P

Average Molecular Weight:

199.0991

Monoisotopic Molecular Weight:

199.024573569

InChI Key:

USRGIUJOYOXOQJ-GBXIJSLDSA-N

InChI:

InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1

CAS number:

1114-81-4

IUPAC Name:

(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid

Traditional IUPAC Name:

phosphothreonine

SMILES:

C[C@@H](OP(O)(O)=O)[C@H](N)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
Phosphoethanolamine
Monoalkyl phosphate
Amino fatty acid
Fatty acyl
Fatty acid
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

threonine derivative (CHEBI:37525 )
O-phosphoamino acid (CHEBI:37525 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	23.5 mg/mL	ALOGPS
logP	-1.9	ALOGPS
logP	-2.7	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.08 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.33 m³·mol^-1	ChemAxon
Polarizability	15.43 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:

Water + L-Threonine O-3-phosphate > Phosphate + L-Threonine

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-6900000000-6cd4ab972cda9b9e8854	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9300000000-7755990490f9b0d090c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-f7e90830423c5451204b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-6900000000-ad7260fbe15d44575ebf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-c0ec684a681c34652a92	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d20cfbbcad9f78ca2901	View in MoNA

References

References:

Kataoka, H., Nakai, K., Katagiri, Y., Makita, M. (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection." Biomed Chromatogr 7:184-188. Pubmed: 7693088
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)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	37525
HMDB ID	HMDB11185
Pubchem Compound ID	3246323
Kegg ID	C12147
ChemSpider ID	2497038
Wikipedia ID	Not Available
BioCyc ID	L-THREONINE-O-3-PHOSPHATE
EcoCyc ID	L-THREONINE-O-3-PHOSPHATE
Ligand Expo	TPO

Enzymes

Protein Details

• Class B acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:: aphA
Locus Tag:: PA1409
Molecular weight:: 38 kDa

Reactions

A phosphate monoester + H(2)O = an alcohol + phosphate.

L-Threonine O-3-phosphate (PAMDB001646)

Structure for L-Threonine O-3-phosphate (PAMDB001646)

Enzymes

Reactions

Transporters