2.0 2012-05-31 14:03:28 -0600 2015-06-03 15:54:40 -0600 ECMDB04049 M2MDB000582 3-Dehydroquinate 3-dehydroquinate is a member of the chemical class known as Cyclitols and Derivatives. These are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms. 3-dehydroquinate is invovled in phenylalanine, tyrosine and tryptophan biosynthesis, and the biosynthesis of secondary metabolites. Dehydroquinate is involved in the shikimate pathway. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. The aroB-encoded enzyme dehydroquinate synthase is the second enzyme of this pathway, and it catalyzes the cyclization of 3-deoxy-D-arabino-heptulosonate-7-phosphate in 3-dehydroquinate. (PMID 17586643) The aroB gene encoding dehydroquinate synthase (DHQS), which is a potential antibiotic target, was identified from the plant-pathogenic bacterium Xanthomonas oryzae pv. (PMID 19052366) 3-Dehydroquinic acid 3DQA 5-De-H-quinate 5-De-H-quinic acid 5-Dehydroquinate 5-Dehydroquinic acid Cyclohexan-1,4,5-triol-3-one-1-carboxylate Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid C7H10O6 190.1507 190.047738052 (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid 3-dehydroquinic acid O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O InChI=1S/C7H10O6/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-,5+,7-/m1/s1 WVMWZWGZRAXUBK-SYTVJDICSA-N Cytosol logp -2.05 ALOGPS logs 0.57 ALOGPS solubility 7.02e+02 g/l ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 3.3 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid ChemAxon average_mass 190.1507 ChemAxon mono_mass 190.047738052 ChemAxon smiles O[C@@H]1C[C@@](O)(CC(=O)[C@H]1O)C(O)=O ChemAxon formula C7H10O6 ChemAxon inchi InChI=1S/C7H10O6/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-,5+,7-/m1/s1 ChemAxon inchikey WVMWZWGZRAXUBK-SYTVJDICSA-N ChemAxon polar_surface_area 115.06 ChemAxon refractivity 38.7 ChemAxon polarizability 16.46 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 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 Secondary Metabolites: Shikimate Pathway The biosynthesis of shikimate 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 an NADPH driven Quinate/shikimate dehydrogenase or a NADPH driven shikimate dehydrogenase 2. Shikimate can also be transported through a shikimate:H+ symporter. PW000985 Metabolic chorismate biosynthesis from 3-dehydroquinate PWY-6163 3-dehydroquinate biosynthesis I PWY-6164 Specdb::CMs 2654 Specdb::CMs 30106 Specdb::CMs 30460 Specdb::CMs 39988 Specdb::CMs 100020 Specdb::CMs 100021 Specdb::CMs 156105 Specdb::NmrOneD 97818 Specdb::NmrOneD 97819 Specdb::NmrOneD 97820 Specdb::NmrOneD 97821 Specdb::NmrOneD 97822 Specdb::NmrOneD 97823 Specdb::NmrOneD 97824 Specdb::NmrOneD 97825 Specdb::NmrOneD 97826 Specdb::NmrOneD 97827 Specdb::NmrOneD 97828 Specdb::NmrOneD 97829 Specdb::NmrOneD 97830 Specdb::NmrOneD 97831 Specdb::NmrOneD 97832 Specdb::NmrOneD 97833 Specdb::NmrOneD 97834 Specdb::NmrOneD 97835 Specdb::NmrOneD 97836 Specdb::NmrOneD 97837 Specdb::MsMs 28433 Specdb::MsMs 28434 Specdb::MsMs 28435 Specdb::MsMs 34991 Specdb::MsMs 34992 Specdb::MsMs 34993 Specdb::MsMs 2719113 Specdb::MsMs 2719114 Specdb::MsMs 2719115 Specdb::MsMs 2963292 Specdb::MsMs 2963293 Specdb::MsMs 2963294 HMDB12710 439351 388474 C00944 32364 DEHYDROQUINATE DQA 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 Ngo, P. T., Natarajan, S., Kim, H., Hung, H. K., Kim, J. G., Lee, B. M., Ahn, Y. J., Kang, L. W. (2008). "Cloning, expression, crystallization and preliminary X-ray crystallographic analysis of 3-dehydroquinate synthase, Xoo1243, from Xanthomonas oryzae pv. oryzae." Acta Crystallogr Sect F Struct Biol Cryst Commun 64:1128-1131. 19052366 de Mendonca, J. D., Ely, F., Palma, M. S., Frazzon, J., Basso, L. A., Santos, D. S. (2007). "Functional characterization by genetic complementation of aroB-encoded dehydroquinate synthase from Mycobacterium tuberculosis H37Rv and its heterologous expression and purification." J Bacteriol 189:6246-6252. 17586643 3-dehydroquinate dehydratase P05194 AROD_ECOLI aroD http://ecmdb.ca/proteins/P05194.xml 3-dehydroquinate synthase P07639 AROB_ECOLI aroB http://ecmdb.ca/proteins/P07639.xml Quinate/shikimate dehydrogenase P0A6D5 YDIB_ECOLI ydiB http://ecmdb.ca/proteins/P0A6D5.xml NAD + Quinate <> 3-Dehydroquinate +2 Hydrogen ion + NADH R01872 3-Dehydroquinate <> 3-Dehydro-shikimate + Water R03084 3-DEHYDROQUINATE-DEHYDRATASE-RXN 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <> 3-Dehydroquinate + Phosphate R03083 3-DEHYDROQUINATE-SYNTHASE-RXN Quinate + NAD <> 3-Dehydroquinate + NADH + Hydrogen ion R01872 Quinate + NADP <> 3-Dehydroquinate + NADPH + Hydrogen ion R06846 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > Phosphate + 3-Dehydroquinate 3-DEHYDROQUINATE-SYNTHASE-RXN NAD(P)⁺ + Quinate NAD(P)H + 3-Dehydroquinate + Hydrogen ion RXN-7967 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > 3-Dehydroquinate + Inorganic phosphate 3-Dehydroquinate > 3-dehydroshikimate + Water Quinate + NAD(P)(+) > 3-Dehydroquinate + NAD(P)H Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate R01872 R06846 3-deoxy-D-arabino-heptulosonate-7-phosphate > Phosphate + 3-Dehydroquinate PW_R002911 3-Dehydroquinate > Water + 3-dehydroshikimate + 3-Dehydro-shikimate PW_R002912 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate