2.0 2012-05-31 13:59:19 -0600 2015-06-03 15:54:24 -0600 ECMDB03484 M2MDB000505 O-Phosphohomoserine O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. It is an intermediate in glycine, serine and threonine metabolism. It is comverted to L-threonine via threonine synthase (EC:4.2.3.1). (KEGG) 2-Amino-4-hydroxy-Butyrate phosphate 2-Amino-4-hydroxy-Butyric acid phosphate 2-amino-4-Hydroxy-butyric acid phosphoric acid Homoserine phosphate Homoserine phosphoric acid L-2-Amino-4-hydroxy-Butyrate dihydrogen phosphate (ester) L-2-Amino-4-hydroxy-Butyric acid dihydrogen phosphate (ester) L-2-amino-4-Hydroxy-butyric acid dihydrogen phosphoric acid (ester) O-Phospho-homoserine O-Phospho-L-homoserine O-phosphohomoserine O-Phosphoryl-homoserine O-Phosphorylhomoserine P-HomoSer C4H10NO6P 199.0991 199.024573569 (2S)-2-amino-4-(phosphonooxy)butanoic acid O-phosphohomoserine 4210-66-6 N[C@@H](CCOP(O)(O)=O)C(O)=O 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 FXDNYOANAXWZHG-VKHMYHEASA-N Solid Cytosol logp -2.34 ALOGPS logs -1.04 ALOGPS solubility 1.81e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 1.52 ChemAxon pka_strongest_basic 9.46 ChemAxon iupac (2S)-2-amino-4-(phosphonooxy)butanoic acid ChemAxon average_mass 199.0991 ChemAxon mono_mass 199.024573569 ChemAxon smiles N[C@@H](CCOP(O)(O)=O)C(O)=O ChemAxon formula C4H10NO6P ChemAxon 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 ChemAxon inchikey FXDNYOANAXWZHG-VKHMYHEASA-N ChemAxon polar_surface_area 130.08 ChemAxon refractivity 37.78 ChemAxon polarizability 15.86 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycine, serine and threonine metabolism ec00260 Vitamin B6 metabolism ec00750 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Secondary Metabolites: threonine biosynthesis from aspartate The biosynthesis of threonine starts with L-aspartic acid being phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000976 Metabolic threonine biosynthesis The biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817 Metabolic threonine biosynthesis from homoserine HOMOSER-THRESYN-PWY Specdb::CMs 2582 Specdb::CMs 38613 Specdb::CMs 137760 Specdb::CMs 145494 Specdb::NmrOneD 22022 Specdb::NmrOneD 22023 Specdb::NmrOneD 22024 Specdb::NmrOneD 22025 Specdb::NmrOneD 22026 Specdb::NmrOneD 22027 Specdb::NmrOneD 22028 Specdb::NmrOneD 22029 Specdb::NmrOneD 22030 Specdb::NmrOneD 22031 Specdb::NmrOneD 22032 Specdb::NmrOneD 22033 Specdb::NmrOneD 22034 Specdb::NmrOneD 22035 Specdb::NmrOneD 22036 Specdb::NmrOneD 22037 Specdb::NmrOneD 22038 Specdb::NmrOneD 22039 Specdb::NmrOneD 22040 Specdb::NmrOneD 22041 Specdb::MsMs 26465 Specdb::MsMs 26466 Specdb::MsMs 26467 Specdb::MsMs 33023 Specdb::MsMs 33024 Specdb::MsMs 33025 Specdb::MsMs 2269078 Specdb::MsMs 2269079 Specdb::MsMs 2269080 Specdb::MsMs 3073377 Specdb::MsMs 3073378 Specdb::MsMs 3073379 HMDB03484 151187 133252 C01102 15961 O-PHOSPHO-L-HOMOSERINE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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Epub 2007 Aug 1. 17665876 Homoserine kinase P00547 KHSE_ECOLI thrB http://ecmdb.ca/proteins/P00547.xml Threonine synthase P00934 THRC_ECOLI thrC http://ecmdb.ca/proteins/P00934.xml Putative phosphonates transport system permease protein phnE P16683 PHNE_ECOLI phnE http://ecmdb.ca/proteins/P16683.xml Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine R01771 HOMOSERKIN-RXN Water + O-Phosphohomoserine <> Phosphate + L-Threonine R01466 THRESYN-RXN Adenosine triphosphate + L-Homoserine <> ADP + O-Phosphohomoserine R01771 HOMOSERKIN-RXN L-Homoserine + Adenosine triphosphate > Hydrogen ion + O-Phosphohomoserine + ADP HOMOSERKIN-RXN O-Phosphohomoserine + Water > Phosphate + L-Threonine R01466 THRESYN-RXN Adenosine triphosphate + L-Homoserine > ADP + O-Phosphohomoserine O-Phosphohomoserine + Water > L-Threonine + Inorganic phosphate L-Homoserine + Adenosine triphosphate + L-Homoserine > Adenosine diphosphate + Hydrogen ion + O-Phosphohomoserine + ADP PW_R002920 O-Phosphohomoserine + Water > Phosphate + L-Threonine + L-Threonine PW_R002921 Water + O-Phosphohomoserine <> Phosphate + L-Threonine Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine Adenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine