2.0 2012-05-31 14:05:52 -0600 2015-09-13 12:56:14 -0600 ECMDB04128 M2MDB000625 Benzeneacetic acid Benzeneacetic acid or phenylacetate is produced by a number of microorganisms including E. coli via the aerobic metabolism of phenylalanine (via oxidation). Phenylacetate is then converted into phenylacetyl-CoA where it is processed into a variety of other compounds mediated by the paa operon (PMID:12846838). Phenylacetate is also produced by a number of plants and is used as a perfumery and flavoring ingredient. It has a sweet taste at low concentrations and has a rose-like odor. It can also be used as a phytotoxin or seed germination inhibitor (Dictionary of Organic Compounds) 2-Phenylacetate 2-Phenylacetic acid 2-phenylethanoate 2-phenylethanoic acid A-Toluate A-Toluic acid Alpha-Toluate Alpha-Toluic acid Benzeneacetate Benzeneacetic acid Benzylformate Benzylformic acid Omega-Phenylacetate Omega-Phenylacetic acid Phenylacetate Phenylacetic acid Phenylethanoate Phenylethanoic acid W-Phenylacetate W-Phenylacetic acid α-Toluate α-Toluic acid C8H8O2 136.1479 136.0524295 2-phenylacetic acid ω-phenylacetic acid 103-82-2 OC(=O)CC1=CC=CC=C1 InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) WLJVXDMOQOGPHL-UHFFFAOYSA-N Solid Cytosol logp 1.72 ALOGPS logs -1.58 ALOGPS solubility 3.61e+00 g/l ALOGPS melting_point 76.7 oC logp 1.61 ChemAxon pka_strongest_acidic 4.55 ChemAxon iupac 2-phenylacetic acid ChemAxon average_mass 136.1479 ChemAxon mono_mass 136.0524295 ChemAxon smiles OC(=O)CC1=CC=CC=C1 ChemAxon formula C8H8O2 ChemAxon inchi InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) ChemAxon inchikey WLJVXDMOQOGPHL-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 37.37 ChemAxon polarizability 13.85 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 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 Styrene degradation ec00643 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 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 Specdb::CMs 1016 Specdb::CMs 2640 Specdb::CMs 29481 Specdb::CMs 31075 Specdb::CMs 31879 Specdb::CMs 37358 Specdb::CMs 162591 Specdb::CMs 1054061 Specdb::EiMs 436 Specdb::NmrOneD 1195 Specdb::NmrOneD 1204 Specdb::NmrOneD 2772 Specdb::NmrOneD 4993 Specdb::NmrOneD 4994 Specdb::NmrOneD 142890 Specdb::NmrOneD 142891 Specdb::NmrOneD 142892 Specdb::NmrOneD 142893 Specdb::NmrOneD 142894 Specdb::NmrOneD 142895 Specdb::NmrOneD 142896 Specdb::NmrOneD 142897 Specdb::NmrOneD 142898 Specdb::NmrOneD 142899 Specdb::NmrOneD 142900 Specdb::NmrOneD 142901 Specdb::NmrOneD 142902 Specdb::NmrOneD 142903 Specdb::NmrOneD 142904 Specdb::NmrOneD 142905 Specdb::NmrOneD 142906 Specdb::NmrOneD 142907 Specdb::NmrOneD 142908 Specdb::NmrOneD 142909 Specdb::MsMs 6130 Specdb::MsMs 178593 Specdb::MsMs 178594 Specdb::MsMs 178595 Specdb::MsMs 180912 Specdb::MsMs 180913 Specdb::MsMs 180914 Specdb::MsMs 438658 Specdb::MsMs 440176 Specdb::MsMs 2252735 Specdb::MsMs 2253762 Specdb::MsMs 2254811 Specdb::MsMs 2255745 Specdb::MsMs 2256898 Specdb::MsMs 2257710 Specdb::MsMs 2258846 Specdb::MsMs 2259708 Specdb::MsMs 2761072 Specdb::MsMs 2761073 Specdb::MsMs 2761074 Specdb::MsMs 2945016 Specdb::MsMs 2945017 Specdb::MsMs 2945018 Specdb::NmrTwoD 1208 HMDB00209 999 10181341 C07086 18401 PAC Phenylacetic_acid Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. 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Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44. http://hmdb.ca/system/metabolites/msds/000/000/147/original/HMDB00209.pdf?1358462709 Phenylacetate-coenzyme A ligase P76085 PAAK_ECOLI paaK http://ecmdb.ca/proteins/P76085.xml Phenylacetaldehyde dehydrogenase P80668 FEAB_ECOLI feaB http://ecmdb.ca/proteins/P80668.xml thioesterase, most active with ring-hydroxylated phenylacetyl-coenzyme A thioesters P76084 paaI http://ecmdb.ca/proteins/P76084.xml Water + NAD + Phenylacetaldehyde <>2 Hydrogen ion + NADH + Benzeneacetic acid R02536 Adenosine triphosphate + Coenzyme A + Benzeneacetic acid <> Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate R02539 Phenylacetaldehyde + NAD + Water <> Benzeneacetic acid + NADH + Hydrogen ion R02536 Phenylacetyl-CoA + Water <> Benzeneacetic acid + Coenzyme A R09840 Phenylacetaldehyde + NAD + Water > Benzeneacetic acid + NADH Adenosine triphosphate + Benzeneacetic acid + CoA > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA Phenylacetaldehyde + NAD + Water > NADH + Hydrogen ion + Benzeneacetic acid PW_R005918 Benzeneacetic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA PW_R005919