2.0 2012-05-31 14:07:52 -0600 2015-09-13 12:56:14 -0600 ECMDB06236 M2MDB000661 Phenylacetaldehyde Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. (PMID: 16910727, 7818768, 15606130) .alpha.-toluic aldehyde 1-Oxo-2-phenylethane 2-Phenylacetaldehyde 2-Phenylethanal A-Phenylacetaldehyde A-Tolualdehyde A-Toluic aldehyde Alpha-Phenylacetaldehyde Alpha-Tolualdehyde Alpha-Toluic aldehyde Benzenacetaldehyde Benzeneacetaldehyde Benzylcarboxaldehyde FEMA No. 2974 Hyacinthin Oxophenylethane Phenacetaldehyde Phenyl-Acetaldehyde Phenylacetaldehyde Phenylacetic aldehyde Phenylethanal α-Phenylacetaldehyde α-Tolualdehyde α-Toluic aldehyde C8H8O 120.1485 120.057514878 2-phenylacetaldehyde phenylacetaldehyde 122-78-1 O=CCC1=CC=CC=C1 InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 DTUQWGWMVIHBKE-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp 1.75 ALOGPS logs -1.76 ALOGPS solubility 2.08e+00 g/l ALOGPS melting_point 120.5-121.5 oC logp 1.45 ChemAxon pka_strongest_acidic 14.98 ChemAxon pka_strongest_basic -7 ChemAxon iupac 2-phenylacetaldehyde ChemAxon average_mass 120.1485 ChemAxon mono_mass 120.057514878 ChemAxon smiles O=CCC1=CC=CC=C1 ChemAxon formula C8H8O ChemAxon inchi InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 ChemAxon inchikey DTUQWGWMVIHBKE-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 36.44 ChemAxon polarizability 12.91 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 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 phenylethylamine degradation I 2PHENDEG-PWY Specdb::CMs 954 Specdb::CMs 960 Specdb::CMs 3424 Specdb::CMs 29540 Specdb::CMs 31533 Specdb::CMs 31534 Specdb::CMs 32185 Specdb::CMs 32186 Specdb::CMs 32208 Specdb::CMs 32209 Specdb::CMs 32210 Specdb::CMs 32211 Specdb::CMs 135391 Specdb::CMs 143125 Specdb::EiMs 671 Specdb::NmrOneD 67932 Specdb::NmrOneD 67933 Specdb::NmrOneD 67934 Specdb::NmrOneD 67935 Specdb::NmrOneD 67936 Specdb::NmrOneD 67937 Specdb::NmrOneD 67938 Specdb::NmrOneD 67939 Specdb::NmrOneD 67940 Specdb::NmrOneD 67941 Specdb::NmrOneD 67942 Specdb::NmrOneD 67943 Specdb::NmrOneD 67944 Specdb::NmrOneD 67945 Specdb::NmrOneD 67946 Specdb::NmrOneD 67947 Specdb::NmrOneD 67948 Specdb::NmrOneD 67949 Specdb::NmrOneD 67950 Specdb::NmrOneD 67951 Specdb::MsMs 2478 Specdb::MsMs 2479 Specdb::MsMs 2480 Specdb::MsMs 6106 Specdb::MsMs 7760 Specdb::MsMs 7761 Specdb::MsMs 7762 Specdb::MsMs 14432 Specdb::MsMs 14433 Specdb::MsMs 14434 Specdb::MsMs 2251780 Specdb::MsMs 2397450 Specdb::MsMs 2397451 Specdb::MsMs 2397452 Specdb::MsMs 2541254 Specdb::MsMs 2541255 Specdb::MsMs 2541256 HMDB06236 998 13876539 C00601 16424 PHENYLACETALDEHYDE HY1 PAA 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 Cho, I. H., Kim, S. Y., Choi, H. K., Kim, Y. S. (2006). "Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.)." J Agric Food Chem 54:6332-6335. 16910727 Watson WP, Munter T, Golding BT: A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics. Chem Res Toxicol. 2004 Dec;17(12):1562-7. 15606130 Sumner SJ, Fennell TR: Review of the metabolic fate of styrene. Crit Rev Toxicol. 1994;24 Suppl:S11-33. 7818768 Sun Zhirong; Hu Xiang; Zhou Ding Wastewater minimization in indirect electrochemical synthesis of phenylacetaldehyde. TheScientificWorldJournal (2002), 2 48-52. http://hmdb.ca/system/metabolites/msds/000/005/361/original/HMDB06236.pdf?1358462404 Primary amine oxidase P46883 AMO_ECOLI tynA http://ecmdb.ca/proteins/P46883.xml Phenylacetaldehyde dehydrogenase P80668 FEAB_ECOLI feaB http://ecmdb.ca/proteins/P80668.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 + NAD + Phenylacetaldehyde <>2 Hydrogen ion + NADH + Benzeneacetic acid R02536 Water + Oxygen + Phenylethylamine > Hydrogen peroxide + Ammonium + Phenylacetaldehyde Phenylacetaldehyde + NAD + Water <> Benzeneacetic acid + NADH + Hydrogen ion R02536 Phenylethylamine + Oxygen + Water <> Phenylacetaldehyde + Ammonia + Hydrogen peroxide R02613 Water + Oxygen + Phenylethylamine > Hydrogen ion + Hydrogen peroxide + Ammonia + Phenylacetaldehyde R02613 AMINEPHEN-RXN Water + NAD + Phenylacetaldehyde <> Hydrogen ion + NADH + phenylacetate PHENDEHYD-RXN Phenylethylamine + Water + Oxygen > Phenylacetaldehyde + Ammonia + Hydrogen peroxide Phenylacetaldehyde + NAD + Water > Benzeneacetic acid + NADH Phenylacetaldehyde + NAD + Water > NADH + Hydrogen ion + Benzeneacetic acid PW_R005918