2.0 2012-05-31 13:02:17 -0600 2015-09-13 12:56:09 -0600 ECMDB00930 M2MDB000204 trans-Cinnamic acid Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. It has a melting point of 133 degrees and a boiling point of 300 degrees. Cinnamic acid has a honey-like odor and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon. It is involved in E. coli's aromatic compound metabolism and 3-phenylpropanoate degradation. Cinnamic acid is also part of the biosynthetic shikimate and phenylpropanoid pathways. Its biosynthesis is performed by the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. &beta;-phenylacrylate &beta;-phenylacrylic acid (2E)-2-Phenyl-2-propenoate (2E)-2-Phenyl-2-propenoic acid (2E)-3-Phenyl-2-propenoate (2E)-3-phenyl-2-Propenoic acid (<i>E</i>)-cinnamate (E)-3-Phenylacrylate (E)-3-Phenylacrylic acid (E)-3-Phenylprop-2-enoate (E)-3-Phenylprop-2-enoic acid (E)-Cinnamate (E)-Cinnamic acid 3-Phenyl-2-propenoate 3-Phenyl-2-propenoic acid <i>trans</i>-cinnamic acid b-Phenylacrylate b-Phenylacrylic acid Beta-Phenylacrylate Beta-Phenylacrylic acid Cinnamate Cinnamic acid Trans-3-Phenyl-2-propenoate Trans-3-Phenyl-2-propenoic acid Trans-3-Phenylacrylate Trans-3-Phenylacrylic acid Trans-b-Carboxystyrene Trans-beta-Carboxystyrene Trans-Cinnamate Trans-Cinnamic acid trans-β-Carboxystyrene β-Phenylacrylate β-Phenylacrylic acid C9H8O2 148.1586 148.0524295 (2E)-3-phenylprop-2-enoic acid cinnamic acid 140-10-3 OC(=O)\C=C\C1=CC=CC=C1 InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ WBYWAXJHAXSJNI-VOTSOKGWSA-N Solid Cytosol Membrane logp 2.38 ALOGPS logs -2.38 ALOGPS solubility 6.18e-01 g/l ALOGPS melting_point 133 oC logp 2.14 ChemAxon pka_strongest_acidic 4.51 ChemAxon iupac (2E)-3-phenylprop-2-enoic acid ChemAxon average_mass 148.1586 ChemAxon mono_mass 148.0524295 ChemAxon smiles OC(=O)\C=C\C1=CC=CC=C1 ChemAxon formula C9H8O2 ChemAxon inchi InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ ChemAxon inchikey WBYWAXJHAXSJNI-VOTSOKGWSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 43.06 ChemAxon polarizability 15.43 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 Microbial metabolism in diverse environments ec01120 2-Oxopent-4-enoate metabolism The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW001890 Metabolic 2-Oxopent-4-enoate metabolism 2 The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW002035 Metabolic cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690 Specdb::CMs 677 Specdb::CMs 678 Specdb::CMs 1245 Specdb::CMs 3206 Specdb::CMs 30247 Specdb::CMs 30895 Specdb::CMs 31264 Specdb::CMs 37847 Specdb::CMs 154695 Specdb::CMs 1081799 Specdb::EiMs 488 Specdb::NmrOneD 1609 Specdb::NmrOneD 2238 Specdb::NmrOneD 2933 Specdb::NmrOneD 5018 Specdb::MsMs 1324 Specdb::MsMs 1325 Specdb::MsMs 1326 Specdb::MsMs 4924 Specdb::MsMs 4925 Specdb::MsMs 4926 Specdb::MsMs 4927 Specdb::MsMs 4928 Specdb::MsMs 4931 Specdb::MsMs 4932 Specdb::MsMs 179667 Specdb::MsMs 179668 Specdb::MsMs 179669 Specdb::MsMs 182001 Specdb::MsMs 182002 Specdb::MsMs 182003 Specdb::MsMs 437390 Specdb::MsMs 437391 Specdb::MsMs 437392 Specdb::MsMs 437393 Specdb::MsMs 437394 Specdb::MsMs 439036 Specdb::MsMs 439616 Specdb::MsMs 439617 Specdb::MsMs 447953 Specdb::NmrTwoD 1048 Specdb::NmrTwoD 1550 HMDB00930 5957728 392447 C10438 15669 CPD-674 TCA trans-Cinnamate Keseler, I. 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Chinese Chemical Letters (2007), 18(3), 272-274. http://hmdb.ca/system/metabolites/msds/000/000/837/original/HMDB00930.pdf?1358896085 3-phenylpropionate/cinnamic acid dioxygenase subunit alpha P0ABR5 HCAE_ECOLI hcaE http://ecmdb.ca/proteins/P0ABR5.xml 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunit P0ABW0 HCAC_ECOLI hcaC http://ecmdb.ca/proteins/P0ABW0.xml 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase component P77650 HCAD_ECOLI hcaD http://ecmdb.ca/proteins/P77650.xml 3-phenylpropionate/cinnamic acid dioxygenase subunit beta Q47140 HCAF_ECOLI hcaF http://ecmdb.ca/proteins/Q47140.xml trans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD R06783 RXN-12072 trans-Cinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD R06783 trans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NAD trans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD PW_R005945 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 90.2 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 360800 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 136.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 544000 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776