2.02012-10-10 12:19:38 -06002015-06-03 17:26:03 -0600ECMDB23159M2MDB0035492-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA is an intermediate in phenylacetate metabolism. It is a substrate for 1,2-phenylacetyl-CoA epoxidase which catalyzes the reduction of phenylacetyl-CoA (PA-CoA) to form 1,2-epoxyphenylacetyl-CoA. The subunit A is the catalytic subunit involved in the incorporation of one atom of molecular oxygen into phenylacetyl-CoAS-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethyl 2-(7-oxabicyclo4.1.0hepta-2,4-dien-6-yl)ethanethioateS-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethyl 2-(7-oxabicyclo4.1.0Hepta-2,4-dien-6-yl)ethanethioic acidC29H42N7O18P3S901.666901.151987801(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(2-{7-oxabicyclo[4.1.0]hepta-2,4-dien-1-yl}acetyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(2-{7-oxabicyclo[4.1.0]hepta-2,4-dien-1-yl}acetyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC12OC1([H])C=CC=C2)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=OInChI=1S/C29H42N7O18P3S/c1-28(2,23(40)26(41)32-8-6-18(37)31-9-10-58-19(38)11-29-7-4-3-5-17(29)52-29)13-50-57(47,48)54-56(45,46)49-12-16-22(53-55(42,43)44)21(39)27(51-16)36-15-35-20-24(30)33-14-34-25(20)36/h3-5,7,14-17,21-23,27,39-40H,6,8-13H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t16-,17?,21-,22-,23+,27-,29?/m1/s1ZTMHVINYLDVBNO-FOGVYBFTSA-Nlogp0.24logs-2.22solubility5.48e+00 g/llogp-4.5pka_strongest_acidic0.83pka_strongest_basic4.79iupac(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(2-{7-oxabicyclo[4.1.0]hepta-2,4-dien-1-yl}acetyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acidaverage_mass901.666mono_mass901.151987801smiles[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC12OC1([H])C=CC=C2)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=OformulaC29H42N7O18P3SinchiInChI=1S/C29H42N7O18P3S/c1-28(2,23(40)26(41)32-8-6-18(37)31-9-10-58-19(38)11-29-7-4-3-5-17(29)52-29)13-50-57(47,48)54-56(45,46)49-12-16-22(53-55(42,43)44)21(39)27(51-16)36-15-35-20-24(30)33-14-34-25(20)36/h3-5,7,14-17,21-23,27,39-40H,6,8-13H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t16-,17?,21-,22-,23+,27-,29?/m1/s1inchikeyZTMHVINYLDVBNO-FOGVYBFTSA-Npolar_surface_area383.14refractivity200.33polarizability80.11rotatable_bond_count22acceptor_count20donor_count9physiological_charge-3formal_charge0Benzoate degradation via CoA ligationec00632Butanoate metabolismec00650Phenylalanine 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.PW000921ec00360MetabolicTryptophan metabolismThe 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
PW000815ec00380Metabolicbeta-Alanine metabolismThe 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.PW000896ec00410MetabolicPropanoate 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.PW000940ec00640Metabolicalpha-Linolenic acid metabolismec00592Lysine degradationec00310Valine, leucine and isoleucine degradationec00280Biosynthesis of unsaturated fatty acidsec01040Fatty 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 degradationec00281Limonene and pinene degradationec00903Caprolactam degradationec00930Microbial metabolism in diverse environmentsec01120Phenylethylamine metabolismThe process of phenylethylamine metabolism starts with 2-phenylethylamine interacting with an oxygen molecule and a water molecule in the periplasmic space through a phenylethylamine oxidase. This reaction results in the release of a hydrogen peroxide, ammonium and phenylacetaldehyde.
Phenylacetaldehyde is introduced into the cytosol and degraded into phenylacetate by reaction with a phenylacetaldehyde dehydrogenase. This reaction involves phenylacetaldehyde interacting with NAD, and a water molecule and then resulting in the release of NADH, and 2 hydrogen ion.
Phenylacetate is then degraded. The first step involves phenylacetate interacting with an coenzyme A and an ATP driven phenylacetate-CoA ligase resulting in the release of a AMP, a diphosphate and a phenylacetyl-CoA. This resulting compound the interacts with a hydrogen ion, NADPH, and oxygen molecule through a ring 1,2-phenylacetyl-CoA epoxidase protein complex resulting in the release of a water molecule, an NADP and a 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA. This compound is then metabolized by a ring 1,2 epoxyphenylacetyl-CoA isomerase resulting in a 2-oxepin-2(3H)-ylideneacetyl-CoA. This compound is then hydrolated through a oxepin-CoA hydrolase resulting in a 3-oxo-5,6-didehydrosuberyl-CoA semialdehyde. This commpound then interacts with a water molecule and NADP driven 3-oxo-5,6-dehydrosuberyl-CoA semialadehyde dehydrogenase resulting in 2 hydrogen ions, a NADPH and a 3-oxo-5,6-didehydrosuberyl-CoA. The resulting compound interacts with a coenzyme A and a 3-oxo-5,6 dehydrosuberyl-CoA thiolase resulting in an acetyl-CoA and a 2,3-didehydroadipyl-CoA. This resulting compound is the hydrated by a 2,3-dehydroadipyl-CoA hydratas resulting in a 3-hydroxyadipyl-CoA whuch is dehydrogenated through an NAD driven 3-hydroxyadipyl-CoA dehydrogenase resulting in a NADH, a hydrogen ion and a 3-oxoadipyl-CoA. The latter compound then interacts with conezyme A through a beta-ketoadipyl-CoA thiolase resulting in an acetyl-CoA and a succinyl-CoA. The succinyl-CoA is then integrated into the TCA cycle.PW002027MetabolicSpecdb::EiMs5073Specdb::NmrOneD303891Specdb::NmrOneD303892Specdb::NmrOneD303893Specdb::NmrOneD303894Specdb::NmrOneD303895Specdb::NmrOneD303896Specdb::NmrOneD303897Specdb::NmrOneD303898Specdb::NmrOneD303899Specdb::NmrOneD303900Specdb::NmrOneD303901Specdb::NmrOneD303902Specdb::NmrOneD303903Specdb::NmrOneD303904Specdb::NmrOneD303905Specdb::NmrOneD303906Specdb::NmrOneD303907Specdb::NmrOneD303908Specdb::NmrOneD303909Specdb::NmrOneD303910Specdb::MsMs24935Specdb::MsMs24936Specdb::MsMs24937Specdb::MsMs31493Specdb::MsMs31494Specdb::MsMs3149546926194C2006263458Probable phenylacetic acid degradation NADH oxidoreductase paaEP76081PAAE_ECOLIpaaEhttp://ecmdb.ca/proteins/P76081.xmlProbable enoyl-CoA hydratase paaFP76082PAAF_ECOLIpaaFhttp://ecmdb.ca/proteins/P76082.xmlProbable enoyl-CoA hydratase paaGP77467PAAG_ECOLIpaaGhttp://ecmdb.ca/proteins/P77467.xmlPhenylacetic acid degradation protein paaBP76078PAAB_ECOLIpaaBhttp://ecmdb.ca/proteins/P76078.xmlPhenylacetic acid degradation protein paaAP76077PAAA_ECOLIpaaAhttp://ecmdb.ca/proteins/P76077.xmlPhenylacetic acid degradation protein paaDP76080PAAD_ECOLIpaaDhttp://ecmdb.ca/proteins/P76080.xmlPhenylacetic acid degradation protein paaCP76079PAAC_ECOLIpaaChttp://ecmdb.ca/proteins/P76079.xmlPhenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA > 2-Oxepin-2(3H)-ylideneacetyl-CoAPhenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoAR098382-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA <> 2-Oxepin-2(3H)-ylideneacetyl-CoAR09837Phenylacetyl-CoA + Hydrogen ion + NADPH + Oxygen > Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoAPW_R005920