2.0 2015-06-08 15:08:39 -0600 2015-08-05 16:22:05 -0600 ECMDB23860 M2MDB005459 trans-2,3-Dehydroacyl-CoA An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any 2,3-trans-enoic acid 2-Hydroxy-2-(4-hydroxyphenyl)acetonitrile 4-Hydroxybenzaldehyde cyanonhydrin a,4-Dihydroxybenzeneacetonitrile alpha,4-Dihydroxybenzeneacetonitrile P-Hydroxymandelonitrile Para-hydroxymandelonitrile α,4-dihydroxybenzeneacetonitrile C8H7NO2 149.1467 149.047678473 2-hydroxy-2-(4-hydroxyphenyl)acetonitrile p-hydroxymandelonitrile OC(C#N)C1=CC=C(O)C=C1 InChI=1S/C8H7NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H HOOOPXDSCKBLFG-UHFFFAOYSA-N logp 0.73 ALOGPS logs -1.25 ALOGPS solubility 8.37e+00 g/l ALOGPS logp 0.65 ChemAxon pka_strongest_acidic 9.46 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac 2-hydroxy-2-(4-hydroxyphenyl)acetonitrile ChemAxon average_mass 149.1467 ChemAxon mono_mass 149.047678473 ChemAxon smiles OC(C#N)C1=CC=C(O)C=C1 ChemAxon formula C8H7NO2 ChemAxon inchi InChI=1S/C8H7NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H ChemAxon inchikey HOOOPXDSCKBLFG-UHFFFAOYSA-N ChemAxon polar_surface_area 64.25 ChemAxon refractivity 39.66 ChemAxon polarizability 14.53 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Benzoate degradation via CoA ligation ec00632 Butanoate metabolism ec00650 Reductive carboxylate cycle (CO2 fixation) ec00720 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 Tryptophan metabolism The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW000815 ec00380 Metabolic beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic alpha-Linolenic acid metabolism ec00592 Lysine degradation ec00310 Valine, leucine and isoleucine degradation ec00280 Biosynthesis of unsaturated fatty acids ec01040 Benzoate degradation via hydroxylation ec00362 Fatty acid elongation in mitochondria ec00062 Fatty acid metabolism This 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 thioesterase PW000796 ec00071 Metabolic Geraniol degradation ec00281 1,4-Dichlorobenzene degradation ec00627 Limonene and pinene degradation ec00903 Caprolactam degradation ec00930 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Specdb::CMs 85867 Specdb::NmrOneD 266688 Specdb::NmrOneD 266689 Specdb::NmrOneD 266690 Specdb::NmrOneD 266691 Specdb::NmrOneD 266692 Specdb::NmrOneD 266693 Specdb::NmrOneD 266694 Specdb::NmrOneD 266695 Specdb::NmrOneD 266696 Specdb::NmrOneD 266697 Specdb::NmrOneD 266698 Specdb::NmrOneD 266699 Specdb::NmrOneD 266700 Specdb::NmrOneD 266701 Specdb::NmrOneD 266702 Specdb::NmrOneD 266703 Specdb::NmrOneD 266704 Specdb::NmrOneD 266705 Specdb::NmrOneD 266706 Specdb::NmrOneD 266707 Specdb::MsMs 23573 Specdb::MsMs 23574 Specdb::MsMs 23575 Specdb::MsMs 30371 Specdb::MsMs 30372 Specdb::MsMs 30373 C00658 (3S)-3-Hydroxyacyl-CoA <> trans-2,3-Dehydroacyl-CoA + trans-3-Enoyl-CoA + Water R02685 R07314 trans-2,3-Dehydroacyl-CoA + NADP <> trans,trans-2,3,4,5-Tetradehydroacyl-CoA + NADPH + Hydrogen ion R04319 trans-2,3-Dehydroacyl-CoA + NADP <> trans,trans-2,3,4,5-Tetradehydroacyl-CoA + NADPH + Hydrogen ion