2.0 2012-05-31 14:27:48 -0600 2015-06-03 17:19:19 -0600 ECMDB20106 M2MDB000954 5-O-(1-Carboxyvinyl)-3-phosphoshikimate 5-o-(1-carboxyvinyl)-3-phosphoshikimate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. The shikimate pathway enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) is the target of the broad spectrum herbicide glyphosate. (PMID 19211556) 5-Enolpyruvylshikimate-3-phosphate (EPSP) synthase (AroA) is a key enzyme in the aromatic amino acid biosynthetic pathway in microorganisms and plants, and is the target of the herbicide glyphosate. (PMID 16469313) 3-Enolpyruvyl-shikimate-5-P 3-Enolpyruvyl-shikimate-5-phosphate 3-Enolpyruvyl-shikimic acid-5-P 3-Enolpyruvyl-shikimic acid-5-phosphoric acid 5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE 5-ENOLPYRUVYLSHIKIMic acid-3-phosphoric acid 5-O-(1-Carboxyvinyl)-3-phosphoshikimate 5-O-(1-Carboxyvinyl)-3-phosphoshikimic acid 5EPS3P EPS EPSP O5-(1-carboxyvinyl)-3-phosphate shikimate O5-(1-Carboxyvinyl)-3-phosphoric acid shikimic acid O5-(1-carboxyvinyl)-3-phosphoshikimate O5-(1-carboxyvinyl)-3-phosphoshikimic acid C10H13O10P 324.178 324.024633148 (3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid (3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid 89771-75-5 O[C@H]1[C@@H](CC(=C[C@H]1OP(O)(O)=O)C(O)=O)OC(=C)C(O)=O InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1 QUTYKIXIUDQOLK-PRJMDXOYSA-N Cytosol logp -0.83 ALOGPS logs -1.76 ALOGPS solubility 5.63e+00 g/l ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 1.31 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid ChemAxon average_mass 324.178 ChemAxon mono_mass 324.024633148 ChemAxon smiles O[C@H]1[C@@H](CC(=C[C@H]1OP(O)(O)=O)C(O)=O)OC(=C)C(O)=O ChemAxon formula C10H13O10P ChemAxon inchi InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1 ChemAxon inchikey QUTYKIXIUDQOLK-PRJMDXOYSA-N ChemAxon polar_surface_area 170.82 ChemAxon refractivity 65.58 ChemAxon polarizability 26.13 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Metabolic pathways eco01100 chorismate biosynthesis from 3-dehydroquinate PWY-6163 Specdb::CMs 3300 Specdb::NmrOneD 257628 Specdb::NmrOneD 257629 Specdb::NmrOneD 257630 Specdb::NmrOneD 257631 Specdb::NmrOneD 257632 Specdb::NmrOneD 257633 Specdb::NmrOneD 257634 Specdb::NmrOneD 257635 Specdb::NmrOneD 257636 Specdb::NmrOneD 257637 Specdb::NmrOneD 257638 Specdb::NmrOneD 257639 Specdb::NmrOneD 257640 Specdb::NmrOneD 257641 Specdb::NmrOneD 257642 Specdb::NmrOneD 257643 Specdb::NmrOneD 257644 Specdb::NmrOneD 257645 Specdb::NmrOneD 257646 Specdb::NmrOneD 257647 Specdb::MsMs 24782 Specdb::MsMs 24783 Specdb::MsMs 24784 Specdb::MsMs 31340 Specdb::MsMs 31341 Specdb::MsMs 31342 439463 388567 C01269 16257 3-ENOLPYRUVYL-SHIKIMATE-5P EPS 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 Funke, T., Yang, Y., Han, H., Healy-Fried, M., Olesen, S., Becker, A., Schonbrunn, E. (2009). "Structural basis of glyphosate resistance resulting from the double mutation Thr97 -> Ile and Pro101 -> Ser in 5-enolpyruvylshikimate-3-phosphate synthase from Escherichia coli." J Biol Chem 284:9854-9860. 19211556 Sun, Y. C., Li, Y., Zhang, H., Yan, H. Q., Dowling, D. N., Wang, Y. P. (2006). "Reconstitution of the enzyme AroA and its glyphosate tolerance by fragment complementation." FEBS Lett 580:1521-1527. 16469313 3-phosphoshikimate 1-carboxyvinyltransferase P0A6D3 AROA_ECOLI aroA http://ecmdb.ca/proteins/P0A6D3.xml Chorismate synthase P12008 AROC_ECOLI aroC http://ecmdb.ca/proteins/P12008.xml Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate R03460 2.5.1.19-RXN 5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate R01714 CHORISMATE-SYNTHASE-RXN 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Phosphate + Chorismate R01714 CHORISMATE-SYNTHASE-RXN Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Chorismate + Inorganic phosphate 5 5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate