2.02012-05-31 14:24:21 -06002015-10-15 16:14:56 -0600ECMDB20041M2MDB0008902-Hydroxy-2,4-pentadienoate2-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 acid2-Hydroxy-2,4-pentadienoate2-Hydroxy-2,4-pentadienoic acid2-Hydroxypent-2,4-dienoate2-Hydroxypent-2,4-dienoic acid2-Hydroxypenta-2,4-dienoate2-Hydroxypenta-2,4-dienoic acid2-Oxopent-4-enoate2-Oxopent-4-enoic acid<i>cis</i>-2-hydroxypenta-2,4-dienoateCis-2-Hydroxypenta-2,4-dienoateCis-2-Hydroxypenta-2,4-dienoic acidHPDOxopent-4-enoateOxopent-4-enoic acidC5H6O3114.0993114.0316940582-oxopent-4-enoateoxopent-4-enoate159694-16-3OC(=O)C(=O)CC=CInChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8)NOXRYJAWRSNUJD-UHFFFAOYSA-NCytosollogp-0.21logs-0.77solubility2.21e+01 g/llogp0.91pka_strongest_acidic3.26pka_strongest_basic-9.7iupac2-oxopent-4-enoateaverage_mass114.0993mono_mass114.031694058smilesOC(=O)C(=O)CC=CformulaC5H6O3inchiInChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8)inchikeyNOXRYJAWRSNUJD-UHFFFAOYSA-Npolar_surface_area57.2refractivity38.1polarizability9.98rotatable_bond_count3acceptor_count3donor_count0physiological_charge-1formal_charge-1Phenylalanine metabolismThe 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.PW000921ec00360MetabolicBenzoate degradation via hydroxylationec00362Ethylbenzene degradationec00642Biphenyl degradationec00621Toluene and xylene degradationec006221,4-Dichlorobenzene degradationec00627Fluorene degradationec00628Carbazole degradationec00629Styrene degradationec00643Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco011002-Oxopent-4-enoate metabolismThe 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 cyclePW001890Metabolic2-Oxopent-4-enoate metabolism 2The 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 cyclePW002035Metaboliccinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-66903-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoateHCAMHPDEG-PWYSpecdb::MsMs1390909Specdb::MsMs1390910Specdb::MsMs13909115280361951C005961113CPD-6761Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.177651952-hydroxy-6-oxononadienedioate/2-hydroxy-6-oxononatrienedioate hydrolaseP77044MHPC_ECOLImhpChttp://ecmdb.ca/proteins/P77044.xml2-keto-4-pentenoate hydrataseP77608MHPD_ECOLImhpDhttp://ecmdb.ca/proteins/P77608.xmlWater + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acidR02603MHPCHYDROL-RXNWater + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoateR06789RXN-12070Water + 2-Hydroxy-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoateR026012-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + WaterR02603MHPCHYDROL-RXN2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acidR067892-Hydroxy-2,4-pentadienoate > 2-oxopent-4-enoateRXN-72824-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoatePW_R0051592-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoatePW_R005161