2.02015-06-04 15:18:24 -06002015-08-05 16:22:04 -0600ECMDB23793M2MDB0043493-Oxoacyl-CoAA group of coenzymes involved in the metabolism of fatty acids(3S)-2-keto-3-Phenylbutanoate(3S)-2-keto-3-Phenylbutanoic acid(3S)-2-keto-3-Phenylbutyrate(3S)-2-keto-3-Phenylbutyric acid(3S)-2-oxo-3-Phenylbutyrate(3S)-2-oxo-3-Phenylbutyric acid(3S)-3-Methyl-2-keto-3-phenylpropanoate(3S)-3-Methyl-2-keto-3-phenylpropanoic acid(3S)-3-Methyl-2-keto-3-phenylpropionate(3S)-3-Methyl-2-keto-3-phenylpropionic acid(3S)-3-Methyl-2-oxo-3-phenylpropanoate(3S)-3-Methyl-2-oxo-3-phenylpropanoic acid(3S)-3-Methyl-2-oxo-3-phenylpropionate(3S)-3-Methyl-2-oxo-3-phenylpropionic acid(3S)-b-Methyl-phenylpyruvate(3S)-b-Methyl-phenylpyruvic acid(3S)-beta-Methyl-phenylpyruvate(3S)-beta-Methyl-phenylpyruvic acid(3S)-β-methyl-phenylpyruvate(3S)-β-methyl-phenylpyruvic acidC10H10O3178.187178.062994182(3S)-2-oxo-3-phenylbutanoic acid(3S)-2-oxo-3-phenylbutanoic acidC[C@H](C(=O)C(O)=O)C1=CC=CC=C1InChI=1S/C10H10O3/c1-7(9(11)10(12)13)8-5-3-2-4-6-8/h2-7H,1H3,(H,12,13)/t7-/m0/s1AXLLOSUYAVXOIN-ZETCQYMHSA-Nlogp1.83logs-2.38solubility7.50e-01 g/llogp2.44pka_strongest_acidic3.42pka_strongest_basic-9.8iupac(3S)-2-oxo-3-phenylbutanoic acidaverage_mass178.187mono_mass178.062994182smilesC[C@H](C(=O)C(O)=O)C1=CC=CC=C1formulaC10H10O3inchiInChI=1S/C10H10O3/c1-7(9(11)10(12)13)8-5-3-2-4-6-8/h2-7H,1H3,(H,12,13)/t7-/m0/s1inchikeyAXLLOSUYAVXOIN-ZETCQYMHSA-Npolar_surface_area54.37refractivity47.29polarizability17.87rotatable_bond_count3acceptor_count3donor_count1physiological_charge-1formal_charge0Butanoate metabolismec00650alpha-Linolenic acid metabolismec00592Valine, leucine and isoleucine degradationec00280Biosynthesis of unsaturated fatty acidsec01040Benzoate degradation via hydroxylationec00362Fatty acid elongation in mitochondriaec00062Fatty acid metabolismThis pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized.
The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterasePW000796ec00071MetabolicGeraniol degradationec00281Ethylbenzene degradationec00642Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Specdb::CMs1088984Specdb::EiMs2199Specdb::MsMs23174Specdb::MsMs23175Specdb::MsMs23176Specdb::MsMs29972Specdb::MsMs29973Specdb::MsMs29974C00264(3S)-3-Hydroxyacyl-CoA + NAD <> 3-Oxoacyl-CoA + NADH + Hydrogen ionR01778 Acyl-CoA + Acetyl-CoA <> Coenzyme A + 3-Oxoacyl-CoAR00391