2.0 2012-05-31 14:26:54 -0600 2015-09-17 15:41:53 -0600 ECMDB20090 M2MDB000938 4-Hydroxy-2-oxopentanoate 4-hydroxy-2-oxopentanoate is a member of the chemical class known as Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. 4-hydroxy-2-oxopentanoate is invovled in Phenylpropionic acid degradation. r 15;80(8):2939-48.) 2-Oxo-4-hydroxyvalerate 2-Oxo-4-hydroxyvaleric acid 2-oxo-4<i>S</i>-hydroxypentanoate 2-Oxo-4S-hydroxypentanoate 2-Oxo-4S-hydroxypentanoic acid 20-Hydroxyleukotriene E4 20-OH-Leukotriene E4 4-Hydroxy-2-keto-pentanoate 4-Hydroxy-2-keto-pentanoic acid 4-Hydroxy-2-ketovalerate 4-Hydroxy-2-ketovaleric acid 4-Hydroxy-2-oxo-pentanoate 4-Hydroxy-2-oxo-pentanoic acid 4-Hydroxy-2-oxo-valerate 4-Hydroxy-2-oxo-valeric acid 4-Hydroxy-2-oxopentanoate 4-Hydroxy-2-oxopentanoic acid 4-Hydroxy-2-oxovalerate 4-Hydroxy-2-oxovaleric acid HKP C5H7O4 131.108 131.034982285 4-hydroxy-2-oxopentanoic acid 4-hydroxy-2-oxopentanoic acid 3318-73-8 CC(O)CC(=O)C([O-])=O InChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h3,6H,2H2,1H3,(H,8,9)/p-1 HFKQINMYQUXOCH-UHFFFAOYSA-M Cytosol logp -0.67 ALOGPS logs -0.06 ALOGPS solubility 1.16e+02 g/l ALOGPS logp -0.098 ChemAxon pka_strongest_acidic 3.11 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 4-hydroxy-2-oxopentanoic acid ChemAxon average_mass 131.108 ChemAxon mono_mass 131.034982285 ChemAxon smiles CC(O)CC(=O)C([O-])=O ChemAxon formula C5H7O4 ChemAxon inchi InChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h3,6H,2H2,1H3,(H,8,9)/p-1 ChemAxon inchikey HFKQINMYQUXOCH-UHFFFAOYSA-M ChemAxon polar_surface_area 74.6 ChemAxon refractivity 28.81 ChemAxon polarizability 11.94 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 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 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 2-oxopentenoate degradation PWY-5162 Specdb::MsMs 23432 Specdb::MsMs 23433 Specdb::MsMs 23434 Specdb::MsMs 30230 Specdb::MsMs 30231 Specdb::MsMs 30232 HMDB12639 124 121 C03589 17655 4-HYDROXY-2-KETOVALERATE 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 4-hydroxy-2-oxovalerate aldolase P51020 HOA_ECOLI mhpE http://ecmdb.ca/proteins/P51020.xml 2-keto-4-pentenoate hydratase P77608 MHPD_ECOLI mhpD http://ecmdb.ca/proteins/P77608.xml Water + 2-Hydroxy-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoate R02601 4-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acid R00750 MHPELY-RXN Acetaldehyde + Pyruvic acid <> 4-Hydroxy-2-oxopentanoate R00750 MHPELY-RXN 2-oxopent-4-enoate + Water > 4-Hydroxy-2-oxopentanoate 2-OXOPENT-4-ENOATE-HYDRATASE-RXN 4-Hydroxy-2-oxopentanoate <> Acetaldehyde + Pyruvic acid MHPELY-RXN 4-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water 2-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate PW_R005161 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + Acetaldehyde PW_R005162