2.0 2012-05-31 13:03:39 -0600 2015-06-03 15:53:40 -0600 ECMDB01024 M2MDB000229 Phosphohydroxypyruvic acid Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG). 2-Oxo-3-(phosphonooxy)-Propanoate 2-Oxo-3-(phosphonooxy)-Propanoic acid 3-p-Hydroxy-pyr 3-P-Hydroxypyruvate 3-P-Hydroxypyruvic acid 3-p-OH-pyr 3-p-OH-pyruvate 3-p-OH-pyruvic acid 3-Phosphohydroxy-pyr 3-Phosphohydroxypyruvate 3-Phosphohydroxypyruvic acid 3-Phosphonooxypyruvate 3-Phosphonooxypyruvic acid 3PHPA Phosphohydroxypyruate Phosphohydroxypyruic acid Phosphohydroxypyruvate Phosphohydroxypyruvic acid C3H5O7P 184.0414 183.977289026 2-oxo-3-(phosphonooxy)propanoic acid phosphohydroxypyruvate 3913-50-6 OC(=O)C(=O)COP(O)(O)=O InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9) LFLUCDOSQPJJBE-UHFFFAOYSA-N Solid Cytosol logp -1.75 ALOGPS logs -1.14 ALOGPS solubility 1.34e+01 g/l ALOGPS logp -0.87 ChemAxon pka_strongest_acidic 1.02 ChemAxon iupac 2-oxo-3-(phosphonooxy)propanoic acid ChemAxon average_mass 184.0414 ChemAxon mono_mass 183.977289026 ChemAxon smiles OC(=O)C(=O)COP(O)(O)=O ChemAxon formula C3H5O7P ChemAxon inchi InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9) ChemAxon inchikey LFLUCDOSQPJJBE-UHFFFAOYSA-N ChemAxon polar_surface_area 121.13 ChemAxon refractivity 30.56 ChemAxon polarizability 12.69 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Glycine, serine and threonine metabolism ec00260 Methane metabolism ec00680 Vitamin B6 metabolism ec00750 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Secondary Metabolites: cysteine biosynthesis from serine The pathway starts with a 3-phosphoglyceric acid interacting with an NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in an NADH, a hydrogen ion and a phosphohydroxypyruvic acid. This compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in a oxoglutaric acid and a DL-D-phosphoserine. The latter compound then interacts with a water molecule through a phosphoserine phosphatase resulting in a phosphate and an L-serine. The L-serine interacts with an acetyl-coa through a serine acetyltransferase resulting in a release of a Coenzyme A and a O-Acetylserine. The O-acetylserine then interacts with a hydrogen sulfide through a O-acetylserine sulfhydrylase A resulting in an acetic acid, a hydrogen ion and an L-cysteine PW000977 Metabolic cysteine biosynthesis The pathway of cysteine biosynthesis is a two-step conversion starting from L-serine and yielding L-cysteine. L-serine biosynthesis is shown for context. L-cysteine can also be synthesized from sulfate derivatives. The process through L-serine involves a serine acetyltransferase that produces a O-acetylserine which reacts together with hydrogen sulfide through a cysteine synthase complex in order to produce L-cysteine and acetic acid. Hydrogen sulfide is produced from a sulfate. Sulfate reacts with sulfate adenylyltransferase to produce adenosine phosphosulfate. This compound in turn is phosphorylated through a adenylyl-sulfate kinase into a phosphoadenosine phosphosulfate which in turn reacts with a phosphoadenosine phosphosulfate reductase to produce a sulfite. The sulfite reacts with a sulfite reductase to produce the hydrogen sulfide. This pathway is regulated at the genetic level in its second step, wtih both cysteine synthase isozymes being under the positive control of the cysteine-responsive transcription factor CysB. It is also subject to very strong feedback inhibition of its first step by the final pathway product, cysteine. Although two cysteine synthase isozymes exist, only cysteine synthase A (CysK) forms a complex with serine acetyltransferase. CysK is also the only one of the two cysteine synthases that is required for cell viability on cysteine-free medium. Both steps in this pathway are reversible. Based on genetic and proteomic data, it appears that the cysteine synthases may actually act as a sulfur scavenging system during sulfur starvation, stripping sulfur off of L-cysteine, generating any number of variant amino acids in the process. PW000800 Metabolic serine biosynthesis and metabolism Serine biosynthesis is a major metabolic pathway in E. coli. Its end product, serine, is not only used in protein synthesis, but also as a precursor for the biosynthesis of glycine, cysteine, tryptophan, and phospholipids. In addition, it directly or indirectly serves as a source of one-carbon units for the biosynthesis of various compounds. The biosynthesis of serine starts with 3-phosphoglyceric acid being metabolized by a NAD driven D-3-phosphoglycerate dehydrogenase / α-ketoglutarate reductase resulting in the release of a NADH, a hydrogen ion and a phosphohydroxypyruvic acid. The latter compound then interacts with an L-glutamic acid through a 3-phosphoserine aminotransferase / phosphohydroxythreonine aminotransferase resulting in oxoglutaric acid and DL-D-phosphoserine. The DL-D-phosphoserine can also be imported into the cytoplasm through a phosphonate ABC transporter. The DL-D-phosphoserine is dephosphorylated by interacting with a water molecule through a phosphoserine phosphatase resulting in the release of a phosphate and an L-serine L-serine is then metabolized by being dehydrated through either a L-serine dehydratase 2 or a L-serine dehydratase 1 resulting in the release of a water molecule, a hydrogen ion and a 2-aminoacrylic acid. The latter compound is an isomer of a 2-iminopropanoate which reacts spontaneously with a water molecule and a hydrogen ion resulting in the release of Ammonium and pyruvic acid. Pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an acetyl-CoA. PW000809 Metabolic homoserine biosynthesis SERSYN-PWY Specdb::CMs 2973 Specdb::CMs 37896 Specdb::CMs 160784 Specdb::NmrOneD 146110 Specdb::NmrOneD 146111 Specdb::NmrOneD 146112 Specdb::NmrOneD 146113 Specdb::NmrOneD 146114 Specdb::NmrOneD 146115 Specdb::NmrOneD 146116 Specdb::NmrOneD 146117 Specdb::NmrOneD 146118 Specdb::NmrOneD 146119 Specdb::NmrOneD 146120 Specdb::NmrOneD 146121 Specdb::NmrOneD 146122 Specdb::NmrOneD 146123 Specdb::NmrOneD 146124 Specdb::NmrOneD 146125 Specdb::NmrOneD 146126 Specdb::NmrOneD 146127 Specdb::NmrOneD 146128 Specdb::NmrOneD 146129 Specdb::MsMs 23018 Specdb::MsMs 23019 Specdb::MsMs 23020 Specdb::MsMs 29816 Specdb::MsMs 29817 Specdb::MsMs 29818 Specdb::MsMs 2276754 Specdb::MsMs 2276755 Specdb::MsMs 2276756 Specdb::MsMs 3092701 Specdb::MsMs 3092702 Specdb::MsMs 3092703 HMDB01024 105 103 C03232 30933 3-P-HYDROXYPYRUVATE HPV Phosphohydroxypyruvic acid 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 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 Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. 23455439 Zhao G, Winkler ME: A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria. J Bacteriol. 1996 Jan;178(1):232-9. 8550422 Achouri Y, Rider MH, Schaftingen EV, Robbi M: Cloning, sequencing and expression of rat liver 3-phosphoglycerate dehydrogenase. Biochem J. 1997 Apr 15;323 ( Pt 2):365-70. 9163325 D-3-phosphoglycerate dehydrogenase P0A9T0 SERA_ECOLI serA http://ecmdb.ca/proteins/P0A9T0.xml Phosphoserine aminotransferase P23721 SERC_ECOLI serC http://ecmdb.ca/proteins/P23721.xml Uncharacterized Nudix hydrolase nudL P43337 NUDL_ECOLI nudL http://ecmdb.ca/proteins/P43337.xml Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine R04173 3-Phosphoglycerate + NAD > Phosphohydroxypyruvic acid + Hydrogen ion + NADH PGLYCDEHYDROG-RXN 3-Phospho-D-glycerate + NAD <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion R01513 Phosphoserine + alpha-Ketoglutarate <> Phosphohydroxypyruvic acid + L-Glutamate R04173 Phosphohydroxypyruvic acid + Water > Hydroxypyruvic acid + Phosphate RXN0-6562 3-Phosphoglycerate + NAD <> Hydrogen ion + Phosphohydroxypyruvic acid + NADH PGLYCDEHYDROG-RXN Phosphoserine + Oxoglutaric acid <> Phosphohydroxypyruvic acid + L-Glutamate PSERTRANSAM-RXN 3-Phospho-D-glycerate + NAD > Phosphohydroxypyruvic acid + NADH R01513 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 3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate R01513 3-Phosphoglyceric acid + NAD + 3-Phosphoglycerate > NADH + Hydrogen ion + Phosphohydroxypyruvic acid PW_R002843 Phosphohydroxypyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + DL-O-Phosphoserine PW_R002844 3 3-Phospho-D-glycerate + NAD <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine