2.02012-05-31 13:02:17 -06002015-09-13 12:56:09 -0600ECMDB00930M2MDB000204trans-Cinnamic acidCinnamic 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.β-phenylacrylateβ-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 acid3-Phenyl-2-propenoate3-Phenyl-2-propenoic acid<i>trans</i>-cinnamic acidb-Phenylacrylateb-Phenylacrylic acidBeta-PhenylacrylateBeta-Phenylacrylic acidCinnamateCinnamic acidTrans-3-Phenyl-2-propenoateTrans-3-Phenyl-2-propenoic acidTrans-3-PhenylacrylateTrans-3-Phenylacrylic acidTrans-b-CarboxystyreneTrans-beta-CarboxystyreneTrans-CinnamateTrans-Cinnamic acidtrans-β-Carboxystyreneβ-Phenylacrylateβ-Phenylacrylic acidC9H8O2148.1586148.0524295(2E)-3-phenylprop-2-enoic acidcinnamic acid140-10-3OC(=O)\C=C\C1=CC=CC=C1InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+WBYWAXJHAXSJNI-VOTSOKGWSA-NSolidCytosolMembranelogp2.38logs-2.38solubility6.18e-01 g/lmelting_point133 oClogp2.14pka_strongest_acidic4.51iupac(2E)-3-phenylprop-2-enoic acidaverage_mass148.1586mono_mass148.0524295smilesOC(=O)\C=C\C1=CC=CC=C1formulaC9H8O2inchiInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+inchikeyWBYWAXJHAXSJNI-VOTSOKGWSA-Npolar_surface_area37.3refractivity43.06polarizability15.43rotatable_bond_count2acceptor_count2donor_count1physiological_charge-1formal_charge0Phenylalanine metabolismThe 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.PW000921ec00360MetabolicMicrobial metabolism in diverse environmentsec011202-Oxopent-4-enoate metabolismThe 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 cyclePW001890Metabolic2-Oxopent-4-enoate metabolism 2The 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 cyclePW002035Metaboliccinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-6690Specdb::CMs677Specdb::CMs678Specdb::CMs1245Specdb::CMs3206Specdb::CMs30247Specdb::CMs30895Specdb::CMs31264Specdb::CMs37847Specdb::CMs154695Specdb::CMs1081799Specdb::EiMs488Specdb::NmrOneD1609Specdb::NmrOneD2238Specdb::NmrOneD2933Specdb::NmrOneD5018Specdb::MsMs1324Specdb::MsMs1325Specdb::MsMs1326Specdb::MsMs4924Specdb::MsMs4925Specdb::MsMs4926Specdb::MsMs4927Specdb::MsMs4928Specdb::MsMs4931Specdb::MsMs4932Specdb::MsMs179667Specdb::MsMs179668Specdb::MsMs179669Specdb::MsMs182001Specdb::MsMs182002Specdb::MsMs182003Specdb::MsMs437390Specdb::MsMs437391Specdb::MsMs437392Specdb::MsMs437393Specdb::MsMs437394Specdb::MsMs439036Specdb::MsMs439616Specdb::MsMs439617Specdb::MsMs447953Specdb::NmrTwoD1048Specdb::NmrTwoD1550HMDB009305957728392447C1043815669CPD-674TCAtrans-CinnamateKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Ishii, 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). 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Chinese Chemical Letters (2007), 18(3), 272-274. http://hmdb.ca/system/metabolites/msds/000/000/837/original/HMDB00930.pdf?13588960853-phenylpropionate/cinnamic acid dioxygenase subunit alphaP0ABR5HCAE_ECOLIhcaEhttp://ecmdb.ca/proteins/P0ABR5.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunitP0ABW0HCAC_ECOLIhcaChttp://ecmdb.ca/proteins/P0ABW0.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase componentP77650HCAD_ECOLIhcaDhttp://ecmdb.ca/proteins/P77650.xml3-phenylpropionate/cinnamic acid dioxygenase subunit betaQ47140HCAF_ECOLIhcaFhttp://ecmdb.ca/proteins/Q47140.xmltrans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR06783RXN-12072trans-Cinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR06783trans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NADtrans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NADPW_R00594548 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h90.2uM0.037 oCBW25113Stationary Phase, glucose limited3608000Ishii, 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 316:593-597.1737977648 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h136.0uM0.037 oCBW25113Stationary Phase, glucose limited5440000Ishii, 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