2.02012-05-31 13:59:19 -06002015-06-03 15:54:24 -0600ECMDB03484M2MDB000505O-PhosphohomoserineO-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 phosphate2-Amino-4-hydroxy-Butyric acid phosphate2-amino-4-Hydroxy-butyric acid phosphoric acidHomoserine phosphateHomoserine phosphoric acidL-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-homoserineO-Phospho-L-homoserineO-phosphohomoserineO-Phosphoryl-homoserineO-PhosphorylhomoserineP-HomoSerC4H10NO6P199.0991199.024573569(2S)-2-amino-4-(phosphonooxy)butanoic acidO-phosphohomoserine4210-66-6N[C@@H](CCOP(O)(O)=O)C(O)=OInChI=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/s1FXDNYOANAXWZHG-VKHMYHEASA-NSolidCytosollogp-2.34logs-1.04solubility1.81e+01 g/llogp-3.2pka_strongest_acidic1.52pka_strongest_basic9.46iupac(2S)-2-amino-4-(phosphonooxy)butanoic acidaverage_mass199.0991mono_mass199.024573569smilesN[C@@H](CCOP(O)(O)=O)C(O)=OformulaC4H10NO6PinchiInChI=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/s1inchikeyFXDNYOANAXWZHG-VKHMYHEASA-Npolar_surface_area130.08refractivity37.78polarizability15.86rotatable_bond_count5acceptor_count6donor_count4physiological_charge-2formal_charge0Glycine, serine and threonine metabolismec00260Vitamin B6 metabolismec00750Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Secondary Metabolites: threonine biosynthesis from aspartateThe 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. PW000976Metabolicthreonine biosynthesisThe 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. PW000817Metabolicthreonine biosynthesis from homoserineHOMOSER-THRESYN-PWYSpecdb::CMs2582Specdb::CMs38613Specdb::CMs137760Specdb::CMs145494Specdb::NmrOneD22022Specdb::NmrOneD22023Specdb::NmrOneD22024Specdb::NmrOneD22025Specdb::NmrOneD22026Specdb::NmrOneD22027Specdb::NmrOneD22028Specdb::NmrOneD22029Specdb::NmrOneD22030Specdb::NmrOneD22031Specdb::NmrOneD22032Specdb::NmrOneD22033Specdb::NmrOneD22034Specdb::NmrOneD22035Specdb::NmrOneD22036Specdb::NmrOneD22037Specdb::NmrOneD22038Specdb::NmrOneD22039Specdb::NmrOneD22040Specdb::NmrOneD22041Specdb::MsMs26465Specdb::MsMs26466Specdb::MsMs26467Specdb::MsMs33023Specdb::MsMs33024Specdb::MsMs33025Specdb::MsMs2269078Specdb::MsMs2269079Specdb::MsMs2269080Specdb::MsMs3073377Specdb::MsMs3073378Specdb::MsMs3073379HMDB03484151187133252C0110215961O-PHOSPHO-L-HOMOSERINEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Connick JH, Heywood GC, Smith DA, Stone TW: O-phosphohomoserine, a naturally occurring analogue of phosphonate amino acid antagonists, is an N-methyl-D-aspartate (NMDA) antagonist in rat hippocampus. Neurosci Lett. 1986 Jul 24;68(2):249-51.3528930Donini S, Percudani R, Credali A, Montanini B, Sartori A, Peracchi A: A threonine synthase homolog from a mammalian genome. Biochem Biophys Res Commun. 2006 Dec 1;350(4):922-8. Epub 2006 Sep 29.17034760Sun G, Yang K, Zhao Z, Guan S, Han X, Gross RW: Shotgun metabolomics approach for the analysis of negatively charged water-soluble cellular metabolites from mouse heart tissue. Anal Chem. 2007 Sep 1;79(17):6629-40. Epub 2007 Aug 1.17665876Homoserine kinaseP00547KHSE_ECOLIthrBhttp://ecmdb.ca/proteins/P00547.xmlThreonine synthaseP00934THRC_ECOLIthrChttp://ecmdb.ca/proteins/P00934.xmlPutative phosphonates transport system permease protein phnEP16683PHNE_ECOLIphnEhttp://ecmdb.ca/proteins/P16683.xmlAdenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-PhosphohomoserineR01771HOMOSERKIN-RXNWater + O-Phosphohomoserine <> Phosphate + L-ThreonineR01466THRESYN-RXNAdenosine triphosphate + L-Homoserine <> ADP + O-PhosphohomoserineR01771HOMOSERKIN-RXNL-Homoserine + Adenosine triphosphate > Hydrogen ion + O-Phosphohomoserine + ADPHOMOSERKIN-RXNO-Phosphohomoserine + Water > Phosphate + L-ThreonineR01466THRESYN-RXNAdenosine triphosphate + L-Homoserine > ADP + O-PhosphohomoserineO-Phosphohomoserine + Water > L-Threonine + Inorganic phosphateL-Homoserine + Adenosine triphosphate + L-Homoserine > Adenosine diphosphate + Hydrogen ion + O-Phosphohomoserine + ADPPW_R002920O-Phosphohomoserine + Water > Phosphate + L-Threonine + L-ThreoninePW_R002921Water + O-Phosphohomoserine <> Phosphate + L-ThreonineAdenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-PhosphohomoserineAdenosine triphosphate + L-Homoserine <> ADP + Hydrogen ion + O-Phosphohomoserine