2.0 2012-05-31 14:08:40 -0600 2015-06-03 15:54:52 -0600 ECMDB06503 M2MDB000676 Phenylacetyl-CoA Phenylacetyl-CoA is an intermediate in the metabolism of phenylacetic acid. Phenylacetyl-CoA is synthesized by the Phenylacetyl-CoA ligase protein paaK using the following reaction: ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA. Phenylacetate-CoA Phenylacetic acid-CoA C29H42N7O17P3S 885.667 885.157073179 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid phenylacetyl-coa 7532-39-0 CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1 InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1 ZIGIFDRJFZYEEQ-CECATXLMSA-N Solid Cytosol logp -0.03 ALOGPS logs -2.44 ALOGPS solubility 3.19e+00 g/l ALOGPS logp -5.1 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 885.667 ChemAxon mono_mass 885.157073179 ChemAxon smiles CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1 ChemAxon formula C29H42N7O17P3S ChemAxon inchi InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1 ChemAxon inchikey ZIGIFDRJFZYEEQ-CECATXLMSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 196.93 ChemAxon polarizability 79.56 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 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 Microbial metabolism in diverse environments ec01120 Phenylethylamine metabolism The 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. PW002027 Metabolic phenylacetate degradation I (aerobic) PWY0-321 Specdb::NmrOneD 74652 Specdb::NmrOneD 74653 Specdb::NmrOneD 74654 Specdb::NmrOneD 74655 Specdb::NmrOneD 74656 Specdb::NmrOneD 74657 Specdb::NmrOneD 74658 Specdb::NmrOneD 74659 Specdb::NmrOneD 74660 Specdb::NmrOneD 74661 Specdb::NmrOneD 74662 Specdb::NmrOneD 74663 Specdb::NmrOneD 74664 Specdb::NmrOneD 74665 Specdb::NmrOneD 74666 Specdb::NmrOneD 74667 Specdb::NmrOneD 74668 Specdb::NmrOneD 74669 Specdb::NmrOneD 74670 Specdb::NmrOneD 74671 Specdb::MsMs 25358 Specdb::MsMs 25359 Specdb::MsMs 25360 Specdb::MsMs 31916 Specdb::MsMs 31917 Specdb::MsMs 31918 Specdb::MsMs 2346497 Specdb::MsMs 2346498 Specdb::MsMs 2346499 Specdb::MsMs 2593027 Specdb::MsMs 2593028 Specdb::MsMs 2593029 HMDB06503 439267 145148 C00582 15537 CPD-207 FAQ 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 Potempska A, Loo YH, Wisniewski HM: On the possible mechanism of phenylacetate neurotoxicity: inhibition of choline acetyltransferase by phenylacetyl-CoA. J Neurochem. 1984 May;42(5):1499-501. 6142928 Probable phenylacetic acid degradation NADH oxidoreductase paaE P76081 PAAE_ECOLI paaE http://ecmdb.ca/proteins/P76081.xml Phenylacetate-coenzyme A ligase P76085 PAAK_ECOLI paaK http://ecmdb.ca/proteins/P76085.xml Phenylacetic acid degradation protein paaB P76078 PAAB_ECOLI paaB http://ecmdb.ca/proteins/P76078.xml Phenylacetic acid degradation protein paaA P76077 PAAA_ECOLI paaA http://ecmdb.ca/proteins/P76077.xml Phenylacetic acid degradation protein paaD P76080 PAAD_ECOLI paaD http://ecmdb.ca/proteins/P76080.xml Phenylacetic acid degradation protein paaC P76079 PAAC_ECOLI paaC http://ecmdb.ca/proteins/P76079.xml thioesterase, most active with ring-hydroxylated phenylacetyl-coenzyme A thioesters P76084 paaI http://ecmdb.ca/proteins/P76084.xml Hydrogen ion + NADPH + Oxygen + Phenylacetyl-CoA > Water + NADP + Ring 1,2-epoxyphenylacetyl-CoA Adenosine triphosphate + Coenzyme A + Benzeneacetic acid <> Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate R02539 Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA R09838 Phenylacetyl-CoA + Water <> Benzeneacetic acid + Coenzyme A R09840 Coenzyme A + phenylacetate + Adenosine triphosphate > Phenylacetyl-CoA + Pyrophosphate + Adenosine monophosphate PHENYLACETATE--COA-LIGASE-RXN Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion > 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water RXN0-2042 Phenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water Adenosine triphosphate + Benzeneacetic acid + CoA > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA Benzeneacetic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA PW_R005919 Phenylacetyl-CoA + Hydrogen ion + NADPH + Oxygen > Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA PW_R005920