2.0 2012-05-31 14:32:26 -0600 2015-09-17 15:42:00 -0600 ECMDB20193 M2MDB001039 Shikimate 3-phosphate Shikimate 3-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. Shikimate 3-phosphate is involved in the shikimate pathway. The shikimate pathway enzyme 5-enolpyruvyl shikimate-3-phosphate synthase (EPSP synthase) has received attention in the past because it is the target of the broad-spectrum herbicide glyphosate. (PMID 16225867) The enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) catalyzes the penultimate step of the shikimate pathway and is the target of the broad-spectrum herbicide glyphosate. (PMID 15736934) 3-Phosphoshikimate 3-Phosphoshikimic acid 5-Phosphoshikimate 5-Phosphoshikimic acid S3P Shikimate 5-phosphate Shikimate-3-P Shikimate-3-Phosphate Shikimate-5-P Shikimate-5-phosphate SHIKIMATE-5P Shikimic acid 3-phosphate Shikimic acid 3-phosphoric acid Shikimic acid 5-phosphate Shikimic acid 5-phosphoric acid Shikimic acid-3-P Shikimic acid-3-phosphoric acid Shikimic acid-5-P Shikimic acid-5-phosphoric acid SHIKIMic acid-5P C7H8O8P 251.108 250.997324955 (3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid 3-phosphoshikimic acid [H][C@@]1(O)CC(=C[C@@]([H])(OP([O-])([O-])=O)[C@@]1([H])O)C([O-])=O InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/p-3/t4-,5-,6+/m1/s1 QYOJSKGCWNAKGW-PBXRRBTRSA-K Cytosol logp -2.07 ALOGPS logs -1.08 ALOGPS solubility 2.10e+01 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid ChemAxon average_mass 251.108 ChemAxon mono_mass 250.997324955 ChemAxon smiles [H][C@@]1(O)CC(=C[C@@]([H])(OP([O-])([O-])=O)[C@@]1([H])O)C([O-])=O ChemAxon formula C7H8O8P ChemAxon inchi InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/p-3/t4-,5-,6+/m1/s1 ChemAxon inchikey QYOJSKGCWNAKGW-PBXRRBTRSA-K ChemAxon polar_surface_area 144.52 ChemAxon refractivity 49.83 ChemAxon polarizability 20.46 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Metabolic pathways eco01100 Chorismate biosynthesis Chorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway is catalyzed by three separate enzymes, all involved in the biosynthesis of Shikimic acid, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent. The biosynthesis of chorismate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving Quinate/shikimate dehydrogenase and shikimate dehydrogenase 2. Shikimic acid is phosphorylated by Shikimate kinase 2 into shikimate 3-phosphate. Shikimate 3- phophate and a phosphoenolpyruvic acid are then joined through a 3-phosphoshikimate 1-carboxyvinyltransferase to produce a 5-enoylpyruvyl-shikimate 3-phosphate while releasing a phosphate. This in turns produces our final product Chorismate through a chorismate synthase. PW000816 Metabolic chorismate biosynthesis from 3-dehydroquinate PWY-6163 Specdb::CMs 2520 Specdb::NmrOneD 254788 Specdb::NmrOneD 254789 Specdb::NmrOneD 254790 Specdb::NmrOneD 254791 Specdb::NmrOneD 254792 Specdb::NmrOneD 254793 Specdb::NmrOneD 254794 Specdb::NmrOneD 254795 Specdb::NmrOneD 254796 Specdb::NmrOneD 254797 Specdb::NmrOneD 254798 Specdb::NmrOneD 254799 Specdb::NmrOneD 254800 Specdb::NmrOneD 254801 Specdb::NmrOneD 254802 Specdb::NmrOneD 254803 Specdb::NmrOneD 254804 Specdb::NmrOneD 254805 Specdb::NmrOneD 254806 Specdb::NmrOneD 254807 Specdb::MsMs 29480 Specdb::MsMs 29481 Specdb::MsMs 29482 Specdb::MsMs 36038 Specdb::MsMs 36039 Specdb::MsMs 36040 Specdb::MsMs 3597220 Specdb::MsMs 3597221 Specdb::MsMs 3597222 Specdb::MsMs 3598265 Specdb::MsMs 3598266 Specdb::MsMs 3598267 1095 108789 C03175 17052 SHIKIMATE-5P S3P 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 Priestman, M. A., Healy, M. L., Funke, T., Becker, A., Schonbrunn, E. (2005). "Molecular basis for the glyphosate-insensitivity of the reaction of 5-enolpyruvylshikimate 3-phosphate synthase with shikimate." FEBS Lett 579:5773-5780. 16225867 Priestman, M. A., Healy, M. L., Becker, A., Alberg, D. G., Bartlett, P. A., Lushington, G. H., Schonbrunn, E. (2005). "Interaction of phosphonate analogues of the tetrahedral reaction intermediate with 5-enolpyruvylshikimate-3-phosphate synthase in atomic detail." Biochemistry 44:3241-3248. 15736934 3-phosphoshikimate 1-carboxyvinyltransferase P0A6D3 AROA_ECOLI aroA http://ecmdb.ca/proteins/P0A6D3.xml Shikimate kinase 1 P0A6D7 AROK_ECOLI aroK http://ecmdb.ca/proteins/P0A6D7.xml Shikimate kinase 2 P0A6E1 AROL_ECOLI aroL http://ecmdb.ca/proteins/P0A6E1.xml Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate R02412 SHIKIMATE-KINASE-RXN Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate R03460 2.5.1.19-RXN Adenosine triphosphate + Shikimic acid <> ADP + Shikimate 3-phosphate R02412 Shikimic acid + Adenosine triphosphate > Hydrogen ion + Shikimate 3-phosphate + ADP SHIKIMATE-KINASE-RXN Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate Adenosine triphosphate + Shikimic acid > ADP + Shikimate 3-phosphate Shikimic acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + shikimate 3-phosphate + ADP + Shikimate 3-phosphate PW_R002915 shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphate PW_R002916 Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate