2.02012-05-31 14:32:38 -06002015-09-17 16:24:21 -0600ECMDB20197M2MDB001043Trans-2,3-DihydroxycinnamateTrans-2,3-dihydroxycinnamate is a member of the chemical class known as Hydroxycinnamic Acid Derivatives. These are compounds containing an cinnamic acid derivative where the benzene ring is hydroxylated. (2<i>E</i>)-3-(2,3-dihydroxyphenyl)prop-2-enoate(2E)-3-(2,3-dihydroxyphenyl)acrylate(2E)-3-(2,3-dihydroxyphenyl)acrylic acid(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid2,3-Dihydroxy-trans-cinnamate2,3-Dihydroxy-trans-cinnamic acid2,3-Dihydroxycinnamate2,3-Dihydroxycinnamic acid3-(2,3-Dihydroxyphenyl)-2-Propenoate3-(2,3-Dihydroxyphenyl)-2-Propenoic acid3-(2,3-Dihydroxyphenyl)acrylate3-(2,3-Dihydroxyphenyl)acrylic acid3-(2,3-Dihydroxyphenyl)prop-2-enoate3-(2,3-Dihydroxyphenyl)prop-2-enoic acidTrans-2,3-Dihydroxycinnamic acidC9H8O4180.1574180.042258744(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acidtrans-2,3-dihydroxycinnamate31082-90-3OC(=O)C=CC1=C(O)C(O)=CC=C1InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)SIUKXCMDYPYCLH-UHFFFAOYSA-NCytosollogp1.66logs-2.04solubility1.66e+00 g/llogp1.53pka_strongest_acidic3.67pka_strongest_basic-6.3iupac(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acidaverage_mass180.1574mono_mass180.042258744smilesOC(=O)C=CC1=C(O)C(O)=CC=C1formulaC9H8O4inchiInChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)inchikeySIUKXCMDYPYCLH-UHFFFAOYSA-Npolar_surface_area77.76refractivity47.02polarizability17.21rotatable_bond_count2acceptor_count4donor_count3physiological_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 environmentsec01120cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-6690Specdb::CMs57160Specdb::CMs58096Specdb::CMs166020Specdb::MsMs78885Specdb::MsMs78886Specdb::MsMs78887Specdb::MsMs139365Specdb::MsMs139366Specdb::MsMs139367Specdb::MsMs2709788Specdb::MsMs2709789Specdb::MsMs2709790Specdb::MsMs2996018Specdb::MsMs2996019Specdb::MsMs299602052821464445343C1262332356CPD-10796Keseler, 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-D114.220805103-phenylpropionate/cinnamic acid dioxygenase subunit alphaP0ABR5HCAE_ECOLIhcaEhttp://ecmdb.ca/proteins/P0ABR5.xml2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenaseP0ABR9MHPB_ECOLImhpBhttp://ecmdb.ca/proteins/P0ABR9.xml3-phenylpropionate/cinnamic acid dioxygenase subunit betaQ47140HCAF_ECOLIhcaFhttp://ecmdb.ca/proteins/Q47140.xml3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenaseP0CI31hcaBhttp://ecmdb.ca/proteins/P0CI31.xml3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylaseP77397MHPA_ECOLImhpAhttp://ecmdb.ca/proteins/P77397.xml3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NADR06787RXN-10040Trans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioateR06788RXN-12073cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADHR06785RXN-12071cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD <> Trans-2,3-Dihydroxycinnamate + NADH + Hydrogen ionR067853-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NADR06787Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioateR06788cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADHtrans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NAD3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NADTrans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioate3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-DihydroxycinnamateR06786 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioateR04376 NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-DihydroxycinnamateR06782 cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion + Trans-2,3-DihydroxycinnamateR06784