2.0 2012-05-31 13:01:05 -0600 2015-09-13 12:56:09 -0600 ECMDB00764 M2MDB000184 Hydrocinnamic acid Hydrocinnamic acid is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases [EC 1.14.12.-] in the pathway phenylalanine metabolism (KEGG). 3-Phenyl-N-propionate 3-Phenyl-N-propionic acid 3-Phenylpropanoate 3-Phenylpropanoic acid 3-Phenylpropionate 3-Phenylpropionic acid B-Phenylpropionate B-Phenylpropionic acid Benzenepropionate Benzenepropionic acid Benzylacetate Benzylacetic acid Beta-Phenylpropionate Beta-Phenylpropionic acid Dihydrocinnamate Dihydrocinnamic acid HCA Hydrocinnamate Hydrocinnamic acid Omega-Phenylpropanoate Omega-Phenylpropanoic acid Phenylpropanoate Phenylpropanoic acid PPA W-Phenylpropanoate W-Phenylpropanoic acid β-Phenylpropionate β-Phenylpropionic acid C9H10O2 150.1745 150.068079564 3-phenylpropanoic acid 3-phenylpropionic acid 501-52-0 OC(=O)CCC1=CC=CC=C1 InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) XMIIGOLPHOKFCH-UHFFFAOYSA-N Solid Cytosol Extra-organism Membrane Periplasm logp 1.84 ALOGPS logs -1.95 ALOGPS solubility 1.70e+00 g/l ALOGPS melting_point 45-48 oC logp 2.06 ChemAxon pka_strongest_acidic 4.73 ChemAxon iupac 3-phenylpropanoic acid ChemAxon average_mass 150.1745 ChemAxon mono_mass 150.068079564 ChemAxon smiles OC(=O)CCC1=CC=CC=C1 ChemAxon formula C9H10O2 ChemAxon inchi InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) ChemAxon inchikey XMIIGOLPHOKFCH-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 41.97 ChemAxon polarizability 15.94 ChemAxon rotatable_bond_count 3 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 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY Specdb::CMs 644 Specdb::CMs 1113 Specdb::CMs 5688 Specdb::CMs 28257 Specdb::CMs 28435 Specdb::CMs 28436 Specdb::CMs 29482 Specdb::CMs 29676 Specdb::CMs 30034 Specdb::CMs 30571 Specdb::CMs 31224 Specdb::CMs 31825 Specdb::CMs 37751 Specdb::CMs 136079 Specdb::CMs 143813 Specdb::CMs 1074856 Specdb::NmrOneD 1530 Specdb::NmrOneD 145250 Specdb::NmrOneD 145251 Specdb::NmrOneD 145252 Specdb::NmrOneD 145253 Specdb::NmrOneD 145254 Specdb::NmrOneD 145255 Specdb::NmrOneD 145256 Specdb::NmrOneD 145257 Specdb::NmrOneD 145258 Specdb::NmrOneD 145259 Specdb::NmrOneD 145260 Specdb::NmrOneD 145261 Specdb::NmrOneD 145262 Specdb::NmrOneD 145263 Specdb::NmrOneD 145264 Specdb::NmrOneD 145265 Specdb::NmrOneD 145266 Specdb::NmrOneD 145267 Specdb::NmrOneD 145268 Specdb::NmrOneD 145269 Specdb::MsMs 1098 Specdb::MsMs 1099 Specdb::MsMs 1100 Specdb::MsMs 4647 Specdb::MsMs 4648 Specdb::MsMs 4649 Specdb::MsMs 4650 Specdb::MsMs 4651 Specdb::MsMs 4652 Specdb::MsMs 4653 Specdb::MsMs 4654 Specdb::MsMs 20072 Specdb::MsMs 20073 Specdb::MsMs 20074 Specdb::MsMs 20714 Specdb::MsMs 20715 Specdb::MsMs 20716 Specdb::MsMs 21623 Specdb::MsMs 21624 Specdb::MsMs 21625 Specdb::MsMs 22265 Specdb::MsMs 22266 Specdb::MsMs 22267 Specdb::MsMs 285579 Specdb::MsMs 373698 Specdb::NmrTwoD 1476 HMDB00764 107 10181339 C05629 3-PHENYLPROPIONATE HCI 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). 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(1999), 18 pp. http://hmdb.ca/system/metabolites/msds/000/000/683/original/HMDB00764.pdf?1358894538 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 Probable 3-phenylpropionic acid transporter Q47142 HCAT_ECOLI hcaT http://ecmdb.ca/proteins/Q47142.xml Putative 3-hydroxyphenylpropionic acid transporter P77589 MHPT_ECOLI mhpT http://ecmdb.ca/proteins/P77589.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 Hydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD Hydrocinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD R06782 HCAMULTI-RXN Hydrocinnamic acid + NADH + Oxygen + Hydrogen ion > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD HCAMULTI-RXN Hydrocinnamic acid + NADH + Oxygen > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD R06782 HCAMULTI-RXN NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-Dihydroxycinnamate R06782 Hydrocinnamic acid + NADH + Oxygen <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol PW_R003850