2.0 2012-05-31 13:56:51 -0600 2015-06-03 15:54:17 -0600 ECMDB02654 M2MDB000461 Phenylethylamine Phenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It is also known as 2-phenylethylamine, and is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer 1-phenylethylamine. (HMDB) In E. coli phenylalanine metabolism, 2-phenylethylamine can be degraded to phenylacetaldehyde in a reversible reaction catalyzed by a primary-amine oxidase (EC:1.4.3.21). (KEGG) &beta;-phenylethylamine (2-Aminoethyl)benzene (2-Aminoethyl)polystyrene 1-Amino-2-phenylethane 1-Phenethylamine 1-Phenyl-2-amino-athan 1-Phenyl-2-amino-athan (GERMAN) 1-Phenyl-2-amino-athan [German] 1-Phenyl-2-aminoethane 1tnj 1utm 1uto 2-Amino-1-phenylethane 2-Amino-fenylethan 2-Amino-fenylethan [Czech] 2-Fenylethylamin 2-Fenylethylamin [Czech] 2-Phenethylamine 2-Phenyl-Ethanamine 2-Phenylethanamine 2-phenylethanamine (ACD/Name 4.0) 2-Phenylethylamine 2-phenylethylamine (ACD/Name 4.0) b Phenethylamine B-Aminoethylbenzene B-Phenethylamine B-Phenylaethylamin B-Phenylaethylamin (german) b-Phenylaethylamin [german] B-Phenylethylamine Benzeneethanamine Benzeneethanamine hydrochloride Beta Phenethylamine Beta-Aminoethylbenzene Beta-Phenethylamine Beta-Phenylaethylamin Beta-phenylaethylamin (german) Beta-Phenylaethylamin [german] Beta-Phenylethylamine Omega-phenylethylamine PEA Phenethylamine Phenethylamine hydrochloride Phenylethylamine Polystyrene A-NH2 β Phenethylamine β-Aminoethylbenzene β-Phenethylamine β-Phenylaethylamin β-Phenylaethylamin (german) β-Phenylaethylamin [german] β-Phenylethylamine C8H11N 121.1796 121.089149357 2-phenylethan-1-amine 2-phenylethylamine 64-04-0 NCCC1=CC=CC=C1 InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 BHHGXPLMPWCGHP-UHFFFAOYSA-N Solid Extra-organism Periplasm logp 1.41 ALOGPS logs -1.74 ALOGPS solubility 2.19e+00 g/l ALOGPS logp 1.39 ChemAxon pka_strongest_basic 9.79 ChemAxon iupac 2-phenylethan-1-amine ChemAxon average_mass 121.1796 ChemAxon mono_mass 121.089149357 ChemAxon smiles NCCC1=CC=CC=C1 ChemAxon formula C8H11N ChemAxon inchi InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 ChemAxon inchikey BHHGXPLMPWCGHP-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 39.29 ChemAxon polarizability 14.35 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 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 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 phenylethylamine degradation I 2PHENDEG-PWY Specdb::CMs 1044 Specdb::CMs 1248 Specdb::CMs 3027 Specdb::CMs 27376 Specdb::CMs 28073 Specdb::CMs 28122 Specdb::CMs 29046 Specdb::CMs 29532 Specdb::CMs 31563 Specdb::CMs 31564 Specdb::CMs 32178 Specdb::CMs 146217 Specdb::EiMs 1837 Specdb::NmrOneD 3950 Specdb::NmrOneD 4232 Specdb::NmrOneD 5052 Specdb::NmrOneD 5053 Specdb::NmrOneD 96898 Specdb::NmrOneD 96899 Specdb::NmrOneD 96900 Specdb::NmrOneD 96901 Specdb::NmrOneD 96902 Specdb::NmrOneD 96903 Specdb::NmrOneD 96904 Specdb::NmrOneD 96905 Specdb::NmrOneD 96906 Specdb::NmrOneD 96907 Specdb::NmrOneD 96908 Specdb::NmrOneD 96909 Specdb::NmrOneD 96910 Specdb::NmrOneD 96911 Specdb::NmrOneD 96912 Specdb::NmrOneD 96913 Specdb::NmrOneD 96914 Specdb::NmrOneD 96915 Specdb::NmrOneD 96916 Specdb::NmrOneD 96917 Specdb::MsMs 20336 Specdb::MsMs 20337 Specdb::MsMs 20338 Specdb::MsMs 21887 Specdb::MsMs 21888 Specdb::MsMs 21889 Specdb::MsMs 441452 Specdb::MsMs 446752 Specdb::MsMs 446753 Specdb::MsMs 446754 Specdb::MsMs 446755 Specdb::MsMs 446756 Specdb::MsMs 446807 Specdb::MsMs 446808 Specdb::MsMs 446809 Specdb::MsMs 446810 Specdb::MsMs 446811 Specdb::MsMs 448397 Specdb::MsMs 448398 Specdb::MsMs 448399 Specdb::MsMs 448400 Specdb::MsMs 448401 Specdb::MsMs 448402 Specdb::MsMs 448403 Specdb::MsMs 448404 HMDB12275 1001 13856352 C05332 18397 PHENYLETHYLAMINE PEA Phenylethylamine 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 Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. 12205654 O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. 7906896 Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. 7360842 Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. 21690383 Primary amine oxidase P46883 AMO_ECOLI tynA http://ecmdb.ca/proteins/P46883.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Water + Oxygen + Phenylethylamine > Hydrogen peroxide + Ammonium + Phenylacetaldehyde Phenylethylamine + Oxygen + Water <> Phenylacetaldehyde + Ammonia + Hydrogen peroxide R02613 Water + Oxygen + Phenylethylamine > Hydrogen ion + Hydrogen peroxide + Ammonia + Phenylacetaldehyde R02613 AMINEPHEN-RXN Phenylethylamine + Water + Oxygen > Phenylacetaldehyde + Ammonia + Hydrogen peroxide Luria-Bertani (LB) media Shake flask 0.43 uM true 0.11 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 1716 446 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911