2.0 2012-05-31 14:24:24 -0600 2015-06-03 17:19:11 -0600 ECMDB20042 M2MDB000891 2-Hydroxy-6-ketononatrienedioate 2-hydroxy-6-ketononatrienedioate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioate (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioate (2E,4Z,7E)-2-hydroxy-6-oxononatrienedioic acid 2-hydroxy-6-ketononatrienedioate 2-Hydroxy-6-ketononatrienedioic acid 2-Hydroxy-6-oxonona-2,4,7-triene-1,9-dioate 2-Hydroxy-6-oxonona-2,4,7-triene-1,9-dioic acid 2-Hydroxy-6-oxonona-2,4,7-trienedioate 2-Hydroxy-6-oxonona-2,4,7-trienedioic acid 2-Hydroxy-6-oxononatrienedioate 2-Hydroxy-6-oxononatrienedioic acid C9H8O6 212.1562 212.032087988 2-hydroxy-6-oxonona-2,4,7-trienedioic acid 2-hydroxy-6-oxonona-2,4,7-trienedioic acid OC(=O)C=CC(=O)C=CC=C(O)C(O)=O InChI=1S/C9H8O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-5,11H,(H,12,13)(H,14,15) WCJYZUFKKTYNLB-UHFFFAOYSA-N Cytosol logp 0.57 ALOGPS logs -2.99 ALOGPS solubility 2.18e-01 g/l ALOGPS logp 0.48 ChemAxon pka_strongest_acidic 2.71 ChemAxon pka_strongest_basic -6.2 ChemAxon iupac 2-hydroxy-6-oxonona-2,4,7-trienedioic acid ChemAxon average_mass 212.1562 ChemAxon mono_mass 212.032087988 ChemAxon smiles OC(=O)C=CC(=O)C=CC=C(O)C(O)=O ChemAxon formula C9H8O6 ChemAxon inchi InChI=1S/C9H8O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-5,11H,(H,12,13)(H,14,15) ChemAxon inchikey WCJYZUFKKTYNLB-UHFFFAOYSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 52.41 ChemAxon polarizability 19.33 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 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 2-Oxopent-4-enoate metabolism The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW001890 Metabolic 2-Oxopent-4-enoate metabolism 2 The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW002035 Metabolic cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690 Specdb::CMs 1086661 Specdb::NmrOneD 289235 Specdb::NmrOneD 289236 Specdb::NmrOneD 289237 Specdb::NmrOneD 289238 Specdb::NmrOneD 289239 Specdb::NmrOneD 289240 Specdb::NmrOneD 289241 Specdb::NmrOneD 289242 Specdb::NmrOneD 289243 Specdb::NmrOneD 289244 Specdb::NmrOneD 289245 Specdb::NmrOneD 289246 Specdb::NmrOneD 289247 Specdb::NmrOneD 289248 Specdb::NmrOneD 289249 Specdb::NmrOneD 289250 Specdb::NmrOneD 289251 Specdb::NmrOneD 289252 Specdb::NmrOneD 289253 Specdb::NmrOneD 289254 Specdb::MsMs 23072 Specdb::MsMs 23073 Specdb::MsMs 23074 Specdb::MsMs 29870 Specdb::MsMs 29871 Specdb::MsMs 29872 5282147 4445344 C12624 31082 CPD0-2184 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 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 Trans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate R06788 RXN-12073 Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate R06789 RXN-12070 Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioate R06788 2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid R06789 Trans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioate 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 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate PW_R005158 2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate PW_R005159