ECMDB: O-Phosphohomoserine (ECMDB03484) (M2MDB000505)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)Transporters (1)XML

Proteins (864)

Record Information

Version

2.0

Creation Date

2012-05-31 13:59:19 -0600

Update Date

2015-06-03 15:54:24 -0600

Secondary Accession Numbers

ECMDB03484

Identification

Name:

O-Phosphohomoserine

Description

O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. It is an intermediate in glycine, serine and threonine metabolism. It is comverted to L-threonine via threonine synthase (EC:4.2.3.1). (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Amino-4-hydroxy-Butyrate phosphate
2-Amino-4-hydroxy-Butyric acid phosphate
2-amino-4-Hydroxy-butyric acid phosphoric acid
Homoserine phosphate
Homoserine phosphoric acid
L-2-Amino-4-hydroxy-Butyrate dihydrogen phosphate (ester)
L-2-Amino-4-hydroxy-Butyric acid dihydrogen phosphate (ester)
L-2-amino-4-Hydroxy-butyric acid dihydrogen phosphoric acid (ester)
O-Phospho-homoserine
O-Phospho-L-homoserine
O-phosphohomoserine
O-Phosphoryl-homoserine
O-Phosphorylhomoserine
P-HomoSer

Chemical Formula:

C₄H₁₀NO₆P

Weight:

Average: 199.0991
Monoisotopic: 199.024573569

InChI Key:

FXDNYOANAXWZHG-VKHMYHEASA-N

InChI:

InChI=1S/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1

CAS number:

4210-66-6

IUPAC Name:

(2S)-2-amino-4-(phosphonooxy)butanoic acid

Traditional IUPAC Name:

O-phosphohomoserine

SMILES:

N[C@@H](CCOP(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
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-phosphorylhomoserine (CHEBI:15961 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-3.82	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	18.1 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	1.52	ChemAxon
pKa (Strongest Basic)	9.46	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	5	ChemAxon
Refractivity	37.78 m³·mol⁻¹	ChemAxon
Polarizability	15.86 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:

Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine
Water + O-Phosphohomoserine <> Phosphate + L-Threonine
Adenosine triphosphate + L-Homoserine <> ADP + O-Phosphohomoserine
L-Homoserine + Adenosine triphosphate > Hydrogen ion + O-Phosphohomoserine + ADP
O-Phosphohomoserine + Water > Phosphate + L-Threonine
Adenosine triphosphate + L-Homoserine > ADP + O-Phosphohomoserine
O-Phosphohomoserine + Water > L-Threonine + Inorganic phosphate
L-Homoserine + Adenosine triphosphate + L-Homoserine > Adenosine diphosphate + Hydrogen ion + O-Phosphohomoserine + ADP
O-Phosphohomoserine + Water > Phosphate + L-Threonine + L-Threonine
Water + O-Phosphohomoserine <> Phosphate + L-Threonine
Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine
Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine

SMPDB Pathways:

Secondary Metabolites: threonine biosynthesis from aspartate	PW000976
threonine biosynthesis	PW000817

KEGG Pathways:

Glycine, serine and threonine metabolism ec00260
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Vitamin B6 metabolism ec00750

EcoCyc Pathways:

threonine biosynthesis from homoserine HOMOSER-THRESYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-32eaea5dd0559c46626e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9740000000-c08eab2934811bd8ba17	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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	splash10-0udi-2920000000-4ad8858fcdd6c7235181	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9400000000-0f8e18482c6cb4d65640	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-5e53d50c26289d23a51d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-6900000000-7771f160a034ddf9f1b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-8d6f322a6a23b8822896	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a90f429c8931d6b68915	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-94d81f86136a653c973b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9300000000-ba13bc26408fc381d706	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-1371bda97f3f9586cda8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-2f91689a76e6cee9ff4d	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:

Connick JH, Heywood GC, Smith DA, Stone TW: O-phosphohomoserine, a naturally occurring analogue of phosphonate amino acid antagonists, is an N-methyl-D-aspartate (NMDA) antagonist in rat hippocampus. Neurosci Lett. 1986 Jul 24;68(2):249-51. Pubmed: 3528930
Donini S, Percudani R, Credali A, Montanini B, Sartori A, Peracchi A: A threonine synthase homolog from a mammalian genome. Biochem Biophys Res Commun. 2006 Dec 1;350(4):922-8. Epub 2006 Sep 29. Pubmed: 17034760
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
Sun G, Yang K, Zhao Z, Guan S, Han X, Gross RW: Shotgun metabolomics approach for the analysis of negatively charged water-soluble cellular metabolites from mouse heart tissue. Anal Chem. 2007 Sep 1;79(17):6629-40. Epub 2007 Aug 1. Pubmed: 17665876
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15961
HMDB ID	HMDB03484
Pubchem Compound ID	151187
Kegg ID	C01102
ChemSpider ID	133252
Wikipedia ID	Not Available
BioCyc ID	O-PHOSPHO-L-HOMOSERINE
EcoCyc ID	O-PHOSPHO-L-HOMOSERINE

Enzymes

Protein Details

1. Homoserine kinase

General function:: Involved in ATP binding
Specific function:: Catalyzes the ATP-dependent phosphorylation of L- homoserine to L-homoserine phosphate. Is also able to phosphorylate the hydroxy group on gamma-carbon of L-homoserine analogs when the functional group at the alpha-position is a carboxyl, an ester, or even a hydroxymethyl group. Neither L- threonine nor L-serine are substrates of the enzyme
Gene Name:: thrB
Uniprot ID:: P00547
Molecular weight:: 33623

Reactions

ATP + L-homoserine = ADP + O-phospho-L-homoserine.

Protein Details

2. 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.

Transporters

Protein Details

1. Putative phosphonates transport system permease protein phnE

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for phosphonates; probably responsible for the translocation of the substrate across the membrane
Gene Name:: phnE
Uniprot ID:: P16683
Molecular weight:: 28383

O-Phosphohomoserine (ECMDB03484) (M2MDB000505)

Structure for #<Compound:0xabe4900c>

Enzymes

Reactions

Reactions

Transporters