2.0 2015-09-08 17:50:03 -0600 2016-09-13 16:35:44 -0600 ECMDB24203 M2MDB006320 5-enolpyruvyl-shikimate 3-phosphate 5-Enolpyruvyl-shikimate 3-phosphate 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) 5-Enolpyruvyl-shikimic acid 3-phosphoric acid (3R,4S,5R)-5-[(1-carboxylatoeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate (3R,4S,5R)-5-[(1-carboxylatoeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate logp -0.11 ALOGPS logs -1.22 ALOGPS solubility 2.38e+01 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-carboxylatoeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate ChemAxon polar_surface_area 182.14 ChemAxon refractivity 85.01 ChemAxon polarizability 24.94 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 1 ChemAxon physiological_charge -4 ChemAxon formal_charge -4 ChemAxon 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 Specdb::MsMs 25802 Specdb::MsMs 25803 Specdb::MsMs 25804 Specdb::MsMs 32360 Specdb::MsMs 32361 Specdb::MsMs 32362 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 shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphate PW_R002916 5-enolpyruvyl-shikimate 3-phosphate > Phosphate + Chorismate PW_R002917