2.02012-07-30 14:55:12 -06002015-06-03 17:21:04 -0600ECMDB21278M2MDB001685QuinateQuinic 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 acid1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylate1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acidAmquinateAmquinate(USAN)Amquinic acidAmquinic acid(usan)AmquinolateAmquinolic acidChinateChinic acidKinateKinic acidL-QuinateL-Quinic acidQuinateQuinic acidC7H12O6192.1666192.063388116(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid(-)-quinic acid17230-85-2O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=OInChI=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/s1AAWZDTNXLSGCEK-WYWMIBKRSA-NSolidCytosolExtra-organismPeriplasmlogp-2.46logs0.60solubility7.65e+02 g/lmelting_point168 °C, 441 K, 334 °Flogp-2.7pka_strongest_acidic3.46pka_strongest_basic-3.2iupac(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acidaverage_mass192.1666mono_mass192.063388116smilesO[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=OformulaC7H12O6inchiInChI=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/s1inchikeyAAWZDTNXLSGCEK-WYWMIBKRSA-Npolar_surface_area118.22refractivity39.71polarizability17.02rotatable_bond_count1acceptor_count6donor_count5physiological_charge-1formal_charge0Phenylalanine, tyrosine and tryptophan biosynthesisec00400Metabolic pathwayseco01100Chorismate biosynthesisChorismate 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. PW000816MetabolicSpecdb::CMs1530Specdb::CMs131948Specdb::CMs139682Specdb::NmrOneD5251Specdb::NmrOneD129258Specdb::NmrOneD129259Specdb::NmrOneD129260Specdb::NmrOneD129261Specdb::NmrOneD129262Specdb::NmrOneD129263Specdb::NmrOneD129264Specdb::NmrOneD129265Specdb::NmrOneD129266Specdb::NmrOneD129267Specdb::NmrOneD129268Specdb::NmrOneD129269Specdb::NmrOneD129270Specdb::NmrOneD129271Specdb::NmrOneD129272Specdb::NmrOneD129273Specdb::NmrOneD129274Specdb::NmrOneD129275Specdb::NmrOneD129276Specdb::NmrOneD129277Specdb::MsMs23741Specdb::MsMs23742Specdb::MsMs23743Specdb::MsMs30539Specdb::MsMs30540Specdb::MsMs30541Specdb::MsMs1471100Specdb::MsMs1471101Specdb::MsMs1471102Specdb::MsMs1471103Specdb::MsMs1471104Specdb::MsMs1471128Specdb::MsMs1471307Specdb::MsMs1472331Specdb::MsMs1472332Specdb::MsMs1472333Specdb::MsMs1472334Specdb::MsMs1472335Specdb::MsMs1472336Specdb::MsMs1472337Specdb::MsMs1472338Specdb::MsMs1472339Specdb::MsMs1472340Specdb::MsMs1472341Specdb::MsMs1472342Specdb::NmrTwoD20682841426433C0029629751QUINATEQICQuinateQuinate/shikimate dehydrogenaseP0A6D5YDIB_ECOLIydiBhttp://ecmdb.ca/proteins/P0A6D5.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlNAD + Quinate <> 3-Dehydroquinate +2 Hydrogen ion + NADHR01872Quinate + NAD <> 3-Dehydroquinate + NADH + Hydrogen ionR01872Quinate + NADP <> 3-Dehydroquinate + NADPH + Hydrogen ionR06846NAD(P)<sup>+</sup> + Quinate NAD(P)H + 3-Dehydroquinate + Hydrogen ionRXN-7967Quinate + NAD(P)(+) > 3-Dehydroquinate + NAD(P)HQuinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimateR01872 R06846