2.0 2012-05-31 14:04:23 -0600 2015-10-23 17:32:56 -0600 ECMDB04081 M2MDB000599 2-Hydroxy-6-ketononadienedicarboxylate 2-hydroxy-6-ketononadienedicarboxylate is an intermediate in phenylalanine metabolism. It is converted from 2,3-dihydroxy-phenylpropanoate by 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (EC:1.13.11.-), and form succinate and cis-2-hydroxypenta-2,4-dienoate by 2-hydroxy-6-ketonona-2,4-dienedioic acid hydrolase (EC:3.7.1.-) (KEGG) (2<i>E</i>,4<i>Z</i>)-2-hydroxy-6-oxonona-2,4-dienedioate (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioic acid 2-Hydroxy-6-keto-nona-2,4-dienedioate 2-Hydroxy-6-keto-nona-2,4-dienedioic acid 2-Hydroxy-6-ketonona-2,4-dienedioate 2-Hydroxy-6-ketonona-2,4-dienedioic acid 2-Hydroxy-6-ketononadienedicarboxylate 2-Hydroxy-6-ketononadienedicarboxylic acid 2-Hydroxy-6-ketononadienedioate 2-Hydroxy-6-ketononadienedioic acid 2-Hydroxy-6-oxo-nona-2,4-diene 1,9-dicarboxylate 2-Hydroxy-6-oxo-nona-2,4-diene 1,9-dicarboxylic acid 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioate 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioic acid 2-Hydroxy-6-oxonona-2,4-dienedioate 2-Hydroxy-6-oxonona-2,4-dienedioic acid C9H8O6 212.158 212.033185137 (2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate (2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate 53-42-9 O\C(=C/C=C/C(=O)CCC([O-])=O)C([O-])=O InChI=1S/C9H10O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-3,11H,4-5H2,(H,12,13)(H,14,15)/p-2/b2-1+,7-3- RFENOVFRMPRRJI-YDCWOTKKSA-L Solid Cytosol logp 0.40 ALOGPS logs -1.53 ALOGPS solubility 7.27e+00 g/l ALOGPS melting_point 152-154 oC logp 0.12 ChemAxon pka_strongest_acidic 3.25 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac (2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate ChemAxon average_mass 212.158 ChemAxon mono_mass 212.033185137 ChemAxon smiles O\C(=C/C=C/C(=O)CCC([O-])=O)C([O-])=O ChemAxon formula C9H8O6 ChemAxon inchi InChI=1S/C9H10O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-3,11H,4-5H2,(H,12,13)(H,14,15)/p-2/b2-1+,7-3- ChemAxon inchikey RFENOVFRMPRRJI-YDCWOTKKSA-L ChemAxon polar_surface_area 117.56 ChemAxon refractivity 73.01 ChemAxon polarizability 19.1 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 1 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Microbial metabolism in diverse environments ec01120 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY Specdb::NmrOneD 289215 Specdb::NmrOneD 289216 Specdb::NmrOneD 289217 Specdb::NmrOneD 289218 Specdb::NmrOneD 289219 Specdb::NmrOneD 289220 Specdb::NmrOneD 289221 Specdb::NmrOneD 289222 Specdb::NmrOneD 289223 Specdb::NmrOneD 289224 Specdb::NmrOneD 289225 Specdb::NmrOneD 289226 Specdb::NmrOneD 289227 Specdb::NmrOneD 289228 Specdb::NmrOneD 289229 Specdb::NmrOneD 289230 Specdb::NmrOneD 289231 Specdb::NmrOneD 289232 Specdb::NmrOneD 289233 Specdb::NmrOneD 289234 21158453 20117996 C04479 19615 CPD-157 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 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase P0ABR9 MHPB_ECOLI mhpB http://ecmdb.ca/proteins/P0ABR9.xml 2-hydroxy-6-oxononadienedioate/2-hydroxy-6-oxononatrienedioate hydrolase P77044 MHPC_ECOLI mhpC http://ecmdb.ca/proteins/P77044.xml 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylate R04376 1.13.11.16-RXN Water + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acid R02603 MHPCHYDROL-RXN 2-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + Water R02603 MHPCHYDROL-RXN 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylate R04376 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioate R04376 2-Hydroxy-6-ketononadienedicarboxylate + Water + 2-Hydroxy-6-ketononatrienedioate <> Succinic acid + Fumaric acid R02603