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Identification |
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YMDB ID | YMDB00258 |
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Name | O-Phosphohomoserine |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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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 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; which is catalyzed by 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. |
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Structure | |
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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
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CAS number | 4210-66-6 |
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Weight | Average: 199.0991 Monoisotopic: 199.024573569 |
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InChI Key | FXDNYOANAXWZHG-VKHMYHEASA-N |
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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 |
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IUPAC Name | (2S)-2-amino-4-(phosphonooxy)butanoic acid |
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Traditional IUPAC Name | O-phosphohomoserine |
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Chemical Formula | C4H10NO6P |
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SMILES | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])OP(=O)(O[H])O[H] |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Glycine, serine and threonine metabolism | ec00260 |  |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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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 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 |
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References |
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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
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Synthesis Reference: | Not Available |
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External Links: | |
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