2.0 2012-07-30 14:55:12 -0600 2015-06-03 17:21:04 -0600 ECMDB21278 M2MDB001685 Quinate Quinic acid is a cyclitol, a cyclic polyol. It is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee. It is a constituent of the tara tannins.; This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A new medicament for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market. ()-quinate ()-quinic acid (-)-quinate (-)-Quinic acid (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylate (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylate 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid Amquinate Amquinate(USAN) Amquinic acid Amquinic acid(usan) Amquinolate Amquinolic acid Chinate Chinic acid Kinate Kinic acid L-Quinate L-Quinic acid Quinate Quinic acid C7H12O6 192.1666 192.063388116 (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid (-)-quinic acid 17230-85-2 O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 AAWZDTNXLSGCEK-WYWMIBKRSA-N Solid Cytosol Extra-organism Periplasm logp -2.46 ALOGPS logs 0.60 ALOGPS solubility 7.65e+02 g/l ALOGPS melting_point 168 °C, 441 K, 334 °F logp -2.7 ChemAxon pka_strongest_acidic 3.46 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid ChemAxon average_mass 192.1666 ChemAxon mono_mass 192.063388116 ChemAxon smiles O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O ChemAxon formula C7H12O6 ChemAxon inchi InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 ChemAxon inchikey AAWZDTNXLSGCEK-WYWMIBKRSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 39.71 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 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 Specdb::CMs 1530 Specdb::CMs 131948 Specdb::CMs 139682 Specdb::NmrOneD 5251 Specdb::NmrOneD 129258 Specdb::NmrOneD 129259 Specdb::NmrOneD 129260 Specdb::NmrOneD 129261 Specdb::NmrOneD 129262 Specdb::NmrOneD 129263 Specdb::NmrOneD 129264 Specdb::NmrOneD 129265 Specdb::NmrOneD 129266 Specdb::NmrOneD 129267 Specdb::NmrOneD 129268 Specdb::NmrOneD 129269 Specdb::NmrOneD 129270 Specdb::NmrOneD 129271 Specdb::NmrOneD 129272 Specdb::NmrOneD 129273 Specdb::NmrOneD 129274 Specdb::NmrOneD 129275 Specdb::NmrOneD 129276 Specdb::NmrOneD 129277 Specdb::MsMs 23741 Specdb::MsMs 23742 Specdb::MsMs 23743 Specdb::MsMs 30539 Specdb::MsMs 30540 Specdb::MsMs 30541 Specdb::MsMs 1471100 Specdb::MsMs 1471101 Specdb::MsMs 1471102 Specdb::MsMs 1471103 Specdb::MsMs 1471104 Specdb::MsMs 1471128 Specdb::MsMs 1471307 Specdb::MsMs 1472331 Specdb::MsMs 1472332 Specdb::MsMs 1472333 Specdb::MsMs 1472334 Specdb::MsMs 1472335 Specdb::MsMs 1472336 Specdb::MsMs 1472337 Specdb::MsMs 1472338 Specdb::MsMs 1472339 Specdb::MsMs 1472340 Specdb::MsMs 1472341 Specdb::MsMs 1472342 Specdb::NmrTwoD 2068 28414 26433 C00296 29751 QUINATE QIC Quinate Quinate/shikimate dehydrogenase P0A6D5 YDIB_ECOLI ydiB http://ecmdb.ca/proteins/P0A6D5.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 NAD + Quinate <> 3-Dehydroquinate +2 Hydrogen ion + NADH R01872 Quinate + NAD <> 3-Dehydroquinate + NADH + Hydrogen ion R01872 Quinate + NADP <> 3-Dehydroquinate + NADPH + Hydrogen ion R06846 NAD(P)⁺ + Quinate NAD(P)H + 3-Dehydroquinate + Hydrogen ion RXN-7967 Quinate + NAD(P)(+) > 3-Dehydroquinate + NAD(P)H Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate R01872 R06846