2.02012-05-31 14:26:54 -06002015-09-17 15:41:53 -0600ECMDB20090M2MDB0009384-Hydroxy-2-oxopentanoate4-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-hydroxyvalerate2-Oxo-4-hydroxyvaleric acid2-oxo-4<i>S</i>-hydroxypentanoate2-Oxo-4S-hydroxypentanoate2-Oxo-4S-hydroxypentanoic acid20-Hydroxyleukotriene E420-OH-Leukotriene E44-Hydroxy-2-keto-pentanoate4-Hydroxy-2-keto-pentanoic acid4-Hydroxy-2-ketovalerate4-Hydroxy-2-ketovaleric acid4-Hydroxy-2-oxo-pentanoate4-Hydroxy-2-oxo-pentanoic acid4-Hydroxy-2-oxo-valerate4-Hydroxy-2-oxo-valeric acid4-Hydroxy-2-oxopentanoate4-Hydroxy-2-oxopentanoic acid4-Hydroxy-2-oxovalerate4-Hydroxy-2-oxovaleric acidHKPC5H7O4131.108131.0349822854-hydroxy-2-oxopentanoic acid4-hydroxy-2-oxopentanoic acid3318-73-8CC(O)CC(=O)C([O-])=OInChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h3,6H,2H2,1H3,(H,8,9)/p-1HFKQINMYQUXOCH-UHFFFAOYSA-MCytosollogp-0.67logs-0.06solubility1.16e+02 g/llogp-0.098pka_strongest_acidic3.11pka_strongest_basic-2.6iupac4-hydroxy-2-oxopentanoic acidaverage_mass131.108mono_mass131.034982285smilesCC(O)CC(=O)C([O-])=OformulaC5H7O4inchiInChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h3,6H,2H2,1H3,(H,8,9)/p-1inchikeyHFKQINMYQUXOCH-UHFFFAOYSA-Mpolar_surface_area74.6refractivity28.81polarizability11.94rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge0Phenylalanine 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 cyclePW002035Metabolic2-oxopentenoate degradationPWY-5162Specdb::MsMs23432Specdb::MsMs23433Specdb::MsMs23434Specdb::MsMs30230Specdb::MsMs30231Specdb::MsMs30232HMDB12639124121C03589176554-HYDROXY-2-KETOVALERATEKeseler, 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 370:17-25.17765195Winder, 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 80:2939-2948.183310644-hydroxy-2-oxovalerate aldolaseP51020HOA_ECOLImhpEhttp://ecmdb.ca/proteins/P51020.xml2-keto-4-pentenoate hydrataseP77608MHPD_ECOLImhpDhttp://ecmdb.ca/proteins/P77608.xmlWater + 2-Hydroxy-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoateR026014-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acidR00750MHPELY-RXNAcetaldehyde + Pyruvic acid <> 4-Hydroxy-2-oxopentanoateR00750MHPELY-RXN2-oxopent-4-enoate + Water > 4-Hydroxy-2-oxopentanoate2-OXOPENT-4-ENOATE-HYDRATASE-RXN4-Hydroxy-2-oxopentanoate <> Acetaldehyde + Pyruvic acidMHPELY-RXN4-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water2-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoatePW_R0051614-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + AcetaldehydePW_R005162