2.0 2012-05-31 14:24:21 -0600 2015-10-15 16:14:56 -0600 ECMDB20041 M2MDB000890 2-Hydroxy-2,4-pentadienoate 2-hydroxy-2,4-pentadienoate is a member of the chemical class known as Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (2E)-2-hydroxypenta-2,4-dienoate (2E)-2-hydroxypenta-2,4-dienoic acid 2-Hydroxy-2,4-pentadienoate 2-Hydroxy-2,4-pentadienoic acid 2-Hydroxypent-2,4-dienoate 2-Hydroxypent-2,4-dienoic acid 2-Hydroxypenta-2,4-dienoate 2-Hydroxypenta-2,4-dienoic acid 2-Oxopent-4-enoate 2-Oxopent-4-enoic acid <i>cis</i>-2-hydroxypenta-2,4-dienoate Cis-2-Hydroxypenta-2,4-dienoate Cis-2-Hydroxypenta-2,4-dienoic acid HPD Oxopent-4-enoate Oxopent-4-enoic acid C5H6O3 114.0993 114.031694058 2-oxopent-4-enoate oxopent-4-enoate 159694-16-3 OC(=O)C(=O)CC=C InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8) NOXRYJAWRSNUJD-UHFFFAOYSA-N Cytosol logp -0.21 ALOGPS logs -0.77 ALOGPS solubility 2.21e+01 g/l ALOGPS logp 0.91 ChemAxon pka_strongest_acidic 3.26 ChemAxon pka_strongest_basic -9.7 ChemAxon iupac 2-oxopent-4-enoate ChemAxon average_mass 114.0993 ChemAxon mono_mass 114.031694058 ChemAxon smiles OC(=O)C(=O)CC=C ChemAxon formula C5H6O3 ChemAxon inchi InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8) ChemAxon inchikey NOXRYJAWRSNUJD-UHFFFAOYSA-N ChemAxon polar_surface_area 57.2 ChemAxon refractivity 38.1 ChemAxon polarizability 9.98 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 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 Benzoate degradation via hydroxylation ec00362 Ethylbenzene degradation ec00642 Biphenyl degradation ec00621 Toluene and xylene degradation ec00622 1,4-Dichlorobenzene degradation ec00627 Fluorene degradation ec00628 Carbazole degradation ec00629 Styrene degradation ec00643 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 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 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY Specdb::MsMs 1390909 Specdb::MsMs 1390910 Specdb::MsMs 1390911 5280361 951 C00596 1113 CPD-6761 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-hydroxy-6-oxononadienedioate/2-hydroxy-6-oxononatrienedioate hydrolase P77044 MHPC_ECOLI mhpC http://ecmdb.ca/proteins/P77044.xml 2-keto-4-pentenoate hydratase P77608 MHPD_ECOLI mhpD http://ecmdb.ca/proteins/P77608.xml Water + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acid R02603 MHPCHYDROL-RXN Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate R06789 RXN-12070 Water + 2-Hydroxy-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoate R02601 2-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + Water R02603 MHPCHYDROL-RXN 2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid R06789 2-Hydroxy-2,4-pentadienoate > 2-oxopent-4-enoate RXN-7282 4-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water 2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate PW_R005159 2-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate PW_R005161