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O-Phosphohomoserine (YMDB00258)

Identification
YMDB IDYMDB00258
NameO-Phosphohomoserine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionO-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
Thumb
MOLSDFPDBSMILESInChI
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 number4210-66-6
WeightAverage: 199.0991
Monoisotopic: 199.024573569
InChI KeyFXDNYOANAXWZHG-VKHMYHEASA-N
InChIInChI=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 NameO-phosphohomoserine
Chemical FormulaC4H10NO6P
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-3.82PhysProp
Predicted Properties
PropertyValueSource
Water Solubility18.1 g/LALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.52ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.78 m³·mol⁻¹ChemAxon
Polarizability15.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
threonine metabolismPW002401 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
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 ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-32eaea5dd0559c46626eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9740000000-c08eab2934811bd8ba17JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2920000000-4ad8858fcdd6c7235181JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9400000000-0f8e18482c6cb4d65640JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-5e53d50c26289d23a51dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-7771f160a034ddf9f1b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8d6f322a6a23b8822896JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a90f429c8931d6b68915JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-94d81f86136a653c973bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9300000000-ba13bc26408fc381d706JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-1371bda97f3f9586cda8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-2f91689a76e6cee9ff4dJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID15961
HMDB IDHMDB03484
Pubchem Compound ID151187
Kegg IDC01102
ChemSpider ID133252
FOODB IDFDB023182
Wikipedia IDNot Available
BioCyc IDO-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.