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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 is a very strong basic compound (based on its pKa). O-Phosphohomoserine exists in all living species, ranging from bacteria to humans. Within yeast, O-phosphohomoserine participates in a number of enzymatic reactions. In particular, O-phosphohomoserine can be biosynthesized from L-homoserine through its interaction with the enzyme homoserine kinase. In addition, O-phosphohomoserine can be converted into L-threonine; which is mediated by the enzyme threonine synthase. In yeast, O-phosphohomoserine is involved in the metabolic pathway called the threonine metabolism pathway.
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 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
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.