2.0 2012-05-31 10:25:19 -0600 2015-06-03 15:53:26 -0600 ECMDB00272 M2MDB000113 Phosphoserine Phosphoserine is phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling. Phosphorylated serine residues are often referred to as phosphoserine. 3-O-Phosphoserine 3-P-Serine 3-Phospho-serine 3-Phosphoserine 3PSer Dexfosfoserine Fosforina L-3-Phosphoserine L-O-Phosphoserine L-O-Serine phosphate L-O-Serine phosphoric acid L-Phosphoserine L-Serine dihydrogen phosphate (ester) L-Serine dihydrogen phosphoric acid (ester) L-Serine phosphate L-Serine phosphoric acid L-Serinephosphate L-Serinephosphorate L-Serinephosphoric acid L-Seryl phosphate L-Seryl phosphoric acid O-Phospho-L-serine P-Ser P-Serine Phosphorylserine Phosphoserine Serine phosphate Serine phosphoric acid Serine-3-p Serine-3-phosphate Serine-3-phosphoric acid Seryl phosphate Seryl phosphoric acid C3H8NO6P 185.0725 185.008923505 (2S)-2-amino-3-(phosphonooxy)propanoic acid phosphoserine 407-41-0 N[C@@H](COP(O)(O)=O)C(O)=O InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1 BZQFBWGGLXLEPQ-REOHCLBHSA-N Solid Cytosol Extra-organism Periplasm logp -2.32 ALOGPS logs -0.97 ALOGPS solubility 1.99e+01 g/l ALOGPS melting_point 170-171 oC logp -3.2 ChemAxon pka_strongest_acidic 1.2 ChemAxon pka_strongest_basic 9.39 ChemAxon iupac (2S)-2-amino-3-(phosphonooxy)propanoic acid ChemAxon average_mass 185.0725 ChemAxon mono_mass 185.008923505 ChemAxon smiles N[C@@H](COP(O)(O)=O)C(O)=O ChemAxon formula C3H8NO6P ChemAxon inchi InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1 ChemAxon inchikey BZQFBWGGLXLEPQ-REOHCLBHSA-N ChemAxon polar_surface_area 130.08 ChemAxon refractivity 32.91 ChemAxon polarizability 13.97 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Glycine, serine and threonine metabolism ec00260 Methane metabolism ec00680 Vitamin B6 metabolism ec00750 Aminoacyl-tRNA biosynthesis ec00970 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 homoserine biosynthesis SERSYN-PWY Specdb::CMs 509 Specdb::CMs 510 Specdb::CMs 511 Specdb::CMs 1492 Specdb::CMs 2586 Specdb::CMs 30393 Specdb::CMs 30394 Specdb::CMs 30657 Specdb::CMs 31111 Specdb::CMs 32179 Specdb::CMs 32180 Specdb::CMs 37396 Specdb::CMs 136676 Specdb::CMs 144410 Specdb::CMs 1056501 Specdb::CMs 1056503 Specdb::CMs 1056504 Specdb::CMs 1056506 Specdb::CMs 1056508 Specdb::NmrOneD 1308 Specdb::NmrOneD 4960 Specdb::NmrOneD 4961 Specdb::NmrOneD 6362 Specdb::NmrOneD 6363 Specdb::NmrOneD 6364 Specdb::NmrOneD 6365 Specdb::NmrOneD 6366 Specdb::NmrOneD 6367 Specdb::NmrOneD 6368 Specdb::NmrOneD 6369 Specdb::NmrOneD 6370 Specdb::NmrOneD 6371 Specdb::NmrOneD 6372 Specdb::NmrOneD 6373 Specdb::NmrOneD 6374 Specdb::NmrOneD 6375 Specdb::NmrOneD 6376 Specdb::NmrOneD 6377 Specdb::NmrOneD 6378 Specdb::NmrOneD 6379 Specdb::NmrOneD 6380 Specdb::NmrOneD 6381 Specdb::MsMs 475 Specdb::MsMs 476 Specdb::MsMs 477 Specdb::MsMs 3895 Specdb::MsMs 3896 Specdb::MsMs 3897 Specdb::MsMs 3898 Specdb::MsMs 3899 Specdb::MsMs 3903 Specdb::MsMs 178479 Specdb::MsMs 178480 Specdb::MsMs 178481 Specdb::MsMs 180798 Specdb::MsMs 180799 Specdb::MsMs 180800 Specdb::MsMs 439096 Specdb::MsMs 446797 Specdb::MsMs 446798 Specdb::MsMs 446799 Specdb::MsMs 446800 Specdb::MsMs 446801 Specdb::MsMs 2226435 Specdb::MsMs 2228262 Specdb::MsMs 2228800 Specdb::MsMs 2230666 Specdb::NmrTwoD 1251 HMDB00272 68841 62074 C01005 15811 3-P-SERINE SEP Phosphoserine 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). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Molina JA, Jimenez-Jimenez FJ, Gomez P, Vargas C, Navarro JA, Orti-Pareja M, Gasalla T, Benito-Leon J, Bermejo F, Arenas J: Decreased cerebrospinal fluid levels of neutral and basic amino acids in patients with Parkinson's disease. J Neurol Sci. 1997 Sep 10;150(2):123-7. 9268238 Barruel, Elena Mery. Biosynthesis of phosphoserine in vitro. Anales Fac. Quim. y Farm. (1960), 12 228-33. Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Phosphoserine phosphatase P0AGB0 SERB_ECOLI serB http://ecmdb.ca/proteins/P0AGB0.xml Phosphoserine aminotransferase P23721 SERC_ECOLI serC http://ecmdb.ca/proteins/P23721.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine R04173 Water + Phosphoserine > Phosphate + L-Serine Phosphoserine + Water <> L-Serine + Phosphate R00582 Phosphoserine + alpha-Ketoglutarate <> Phosphohydroxypyruvic acid + L-Glutamate R04173 Phosphoserine + Oxoglutaric acid <> Phosphohydroxypyruvic acid + L-Glutamate PSERTRANSAM-RXN Phosphoserine + Oxoglutaric acid > Phosphohydroxypyruvic acid + L-Glutamate PSERTRANSAM-RXN Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid R04173 Phosphoserine + O-Phospho-D-serine + Water <> L-Serine + D-Serine + Phosphate R00582 R02853 Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine