O-Phosphohomoserine (YMDB00258)

Identification

YMDB ID

YMDB00258

Name

O-Phosphohomoserine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

O-Phosphohomoserine, also known as homoserine phosphate, 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. O-Phosphohomoserine exists in all living species, ranging from bacteria to plants to humans. In yeast, O-phosphohomoserine is involved in the metabolic pathway called the threonine metabolism pathway. Based on a literature review a significant number of articles have been published on O-Phosphohomoserine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-amino-4-hydroxy-Butyric acid phosphate
Homoserine phosphate
L-2-amino-4-hydroxy-Butyric acid dihydrogen phosphate (ester)
O-Phospho-homoserine
O-Phospho-L-homoserine
L-Homoserine, dihydrogen phosphate (ester)
Homoserine phosphoric acid
L-Homoserine, dihydrogen phosphoric acid (ester)
O-Phosphohomoserine, (DL)-isomer

CAS number

4210-66-6

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

IUPAC Name

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

Traditional IUPAC Name

O-phosphohomoserine

Chemical Formula

C₄H₁₀NO₆P

SMILES

[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])OP(=O)(O[H])O[H]

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
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

Organoleptic Properties

Not Available

SMPDB Pathways

threonine metabolism

PW002401

KEGG Pathways

Glycine, serine and threonine metabolism

ec00260

SMPDB Reactions

L-Homoserine + Adenosine triphosphate → ADP + hydron + O-Phosphohomoserine

O-Phosphohomoserine + water → phosphate + L-Threonine

KEGG Reactions

Adenosine triphosphate + L-Homoserine → hydron + O-Phosphohomoserine + ADP

water + O-Phosphohomoserine → phosphate + L-Threonine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-32eaea5dd0559c46626e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9740000000-c08eab2934811bd8ba17	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2920000000-4ad8858fcdd6c7235181	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9400000000-0f8e18482c6cb4d65640	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-5e53d50c26289d23a51d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-6900000000-7771f160a034ddf9f1b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-8d6f322a6a23b8822896	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a90f429c8931d6b68915	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-94d81f86136a653c973b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9300000000-ba13bc26408fc381d706	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-1371bda97f3f9586cda8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-2f91689a76e6cee9ff4d	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Huo, X., Viola, R. E. (1996). "Substrate specificity and identification of functional groups of homoserine kinase from Escherichia coli." Biochemistry 35:16180-16185.8973190
Ramos, C., Calderon, I. L. (1994). "Biochemical evidence that the Saccharomyces cerevisiae THR4 gene encodes threonine synthetase." FEBS Lett 351:357-359.8082795

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15961
HMDB ID	HMDB03484
Pubchem Compound ID	151187
Kegg ID	C01102
ChemSpider ID	133252
FOODB ID	FDB023182
Wikipedia ID	Not Available
BioCyc 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
Gene Name:: THR1
Uniprot ID:: P17423
Molecular weight:: 38712.0

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
Gene Name:: THR4
Uniprot ID:: P16120
Molecular weight:: 57473.69922

Reactions

O-phospho-L-homoserine + H(2)O → L-threonine + phosphate.

Structure for #<Compound:0xaf449d14>

Enzymes

Reactions

Reactions