2.0 2012-05-31 14:32:38 -0600 2015-09-17 16:24:21 -0600 ECMDB20197 M2MDB001043 Trans-2,3-Dihydroxycinnamate Trans-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 acid 2,3-Dihydroxy-trans-cinnamate 2,3-Dihydroxy-trans-cinnamic acid 2,3-Dihydroxycinnamate 2,3-Dihydroxycinnamic acid 3-(2,3-Dihydroxyphenyl)-2-Propenoate 3-(2,3-Dihydroxyphenyl)-2-Propenoic acid 3-(2,3-Dihydroxyphenyl)acrylate 3-(2,3-Dihydroxyphenyl)acrylic acid 3-(2,3-Dihydroxyphenyl)prop-2-enoate 3-(2,3-Dihydroxyphenyl)prop-2-enoic acid Trans-2,3-Dihydroxycinnamic acid C9H8O4 180.1574 180.042258744 (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid trans-2,3-dihydroxycinnamate 31082-90-3 OC(=O)C=CC1=C(O)C(O)=CC=C1 InChI=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-N Cytosol logp 1.66 ALOGPS logs -2.04 ALOGPS solubility 1.66e+00 g/l ALOGPS logp 1.53 ChemAxon pka_strongest_acidic 3.67 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 180.1574 ChemAxon mono_mass 180.042258744 ChemAxon smiles OC(=O)C=CC1=C(O)C(O)=CC=C1 ChemAxon formula C9H8O4 ChemAxon inchi InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12) ChemAxon inchikey SIUKXCMDYPYCLH-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 47.02 ChemAxon polarizability 17.21 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 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 cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690 Specdb::CMs 57160 Specdb::CMs 58096 Specdb::CMs 166020 Specdb::MsMs 78885 Specdb::MsMs 78886 Specdb::MsMs 78887 Specdb::MsMs 139365 Specdb::MsMs 139366 Specdb::MsMs 139367 Specdb::MsMs 2709788 Specdb::MsMs 2709789 Specdb::MsMs 2709790 Specdb::MsMs 2996018 Specdb::MsMs 2996019 Specdb::MsMs 2996020 5282146 4445343 C12623 32356 CPD-10796 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 3-phenylpropionate/cinnamic acid dioxygenase subunit alpha P0ABR5 HCAE_ECOLI hcaE http://ecmdb.ca/proteins/P0ABR5.xml 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase P0ABR9 MHPB_ECOLI mhpB http://ecmdb.ca/proteins/P0ABR9.xml 3-phenylpropionate/cinnamic acid dioxygenase subunit beta Q47140 HCAF_ECOLI hcaF http://ecmdb.ca/proteins/Q47140.xml 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase P0CI31 hcaB http://ecmdb.ca/proteins/P0CI31.xml 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase P77397 MHPA_ECOLI mhpA http://ecmdb.ca/proteins/P77397.xml 3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD R06787 RXN-10040 Trans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate R06788 RXN-12073 cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADH R06785 RXN-12071 cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD <> Trans-2,3-Dihydroxycinnamate + NADH + Hydrogen ion R06785 3-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NAD R06787 Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioate R06788 cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADH trans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NAD 3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD Trans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioate 3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate R06786 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioate R04376 NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-Dihydroxycinnamate R06782 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-Dihydroxycinnamate R06784