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Identification
YMDB IDYMDB00355
NameO-Phospho-4-hydroxy-L-threonine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionO-Phospho-4-hydroxy-L-threonine, also known as 4-(phosphonooxy)-threonine, 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-Phospho-4-hydroxy-L-threonine is a very strong basic compound (based on its pKa). O-Phospho-4-hydroxy-L-threonine exists in all living species, ranging from bacteria to humans. Within yeast, O-phospho-4-hydroxy-L-threonine participates in a number of enzymatic reactions. In particular, O-phospho-4-hydroxy-L-threonine and oxoglutaric acid can be biosynthesized from 2-oxo-3-hydroxy-4-phosphobutanoic acid and L-glutamic acid through its interaction with the enzyme 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase. In addition, O-phospho-4-hydroxy-L-threonine can be converted into 2-amino-3-oxo-4-phosphonooxybutyrate through its interaction with the enzyme 4-hydroxy-L-threonine phosphate dehydrogenase, nad-dependent. In yeast, O-phospho-4-hydroxy-L-threonine is involved in the metabolic pathway called the vitamin B6 pathway.
Structure
Thumb
Synonyms
  • 4-(Phosphonooxy)-L-threonine
  • 4-(Phosphonooxy)-threonine
  • 4-phosphonooxy-L-threonine
  • O-Phospho-4-hydroxy-L-threonine
  • 4-Phosphooxy-L-threonine
  • 4-Phospho-hydroxy-threonine
  • 4-(Phosphohydroxy)-L-threonine
  • 4-Phosphohydroxythreonine
  • 4-Phosphothreonine
CAS numberNot Available
WeightAverage: 215.0985
Monoisotopic: 215.019488191
InChI KeyFKHAKIJOKDGEII-GBXIJSLDSA-N
InChIInChI=1S/C4H10NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h2-3,6H,1,5H2,(H,7,8)(H2,9,10,11)/t2-,3+/m1/s1
IUPAC Name(2S,3S)-2-amino-3-hydroxy-4-(phosphonooxy)butanoic acid
Traditional IUPAC Name4-(phosphonooxy)-L-threonine
Chemical FormulaC4H10NO7P
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])[C@]([H])(O[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
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Monoalkyl phosphate
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility22.7 g/LALOGPS
logP-2.4ALOGPS
logP-3.9ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)8.93ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area150.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.88 m³·mol⁻¹ChemAxon
Polarizability16.6 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
Vitamin B6PW002488 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acidO-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
O-Phospho-4-hydroxy-L-threonine + NADNADH + hydron + 2-Amino-3-oxo-4-phosphonooxybutyrate
KEGG Reactions
water + O-Phospho-4-hydroxy-L-threoninephosphate + 4-Hydroxy-L-threonine
L-Glutamic acid + 2-Oxo-3-hydroxy-4-phosphobutanoic acidOxoglutaric acid + O-Phospho-4-hydroxy-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, Positivesplash10-0002-9200000000-a8f91387710592709ff8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ow-9711000000-89a880807057686a60b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-2920000000-c23edaafe01dd32ccd6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9600000000-fd8c6ec273c259b6d693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9300000000-42e18773c2868e50da83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mj-9850000000-0cd651cd24395dbae4a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-a925d7c6b56522b6d34bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c41cf86b2bcca517868JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • 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 ID18336
HMDB IDHMDB06802
Pubchem Compound ID1006
Kegg IDC06055
ChemSpider ID389731
FOODB IDFDB024088
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine
Gene Name:
SER1
Uniprot ID:
P33330
Molecular weight:
43415.19922
Reactions
O-phospho-L-serine + 2-oxoglutarate → 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate → (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.
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.