2.0 2012-05-31 14:04:26 -0600 2015-06-03 15:54:43 -0600 ECMDB04083 M2MDB000600 3-(3-Hydroxyphenyl)propionate 3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID 15479001, 12663291). -(3-Hydroxyphenyl)propionate -(3-Hydroxyphenyl)propionic acid -(m-hydroxyphenyl)propionate -(m-hydroxyphenyl)propionic acid 3-(3-Hydroxy-phenyl)-propanoate 3-(3-Hydroxy-phenyl)-propanoic acid 3-(3-Hydroxy-phenyl)-propionate 3-(3-hydroxy-phenyl)-propionic acid 3-(3-Hydroxyphenyl)propanoate 3-(3-Hydroxyphenyl)propanoic acid 3-(3-Hydroxyphenyl)propionic acid 3-(m-Hydroxyphenyl)propionate 3-(m-Hydroxyphenyl)propionic acid 3-Hydroxy-Benzenepropanoate 3-Hydroxy-Benzenepropanoic acid 3-Hydroxybenzenepropanoate 3-Hydroxybenzenepropanoic acid 3-Hydroxydihydrocinnamate 3-Hydroxydihydrocinnamic acid 3-Hydroxyhydrocinnamate 3-hydroxyhydrocinnamic acid 3-Hydroxyphenylpropanoate 3-Hydroxyphenylpropanoic acid 3-Hydroxyphenylpropionate 3-Hydroxyphenylpropionic acid 3HPP B-(3-Hydroxyphenyl)propionate B-(3-Hydroxyphenyl)propionic acid B-(m-Hydroxyphenyl)propionate B-(m-Hydroxyphenyl)propionic acid Beta-(3-Hydroxyphenyl)propionate Beta-(3-Hydroxyphenyl)propionic acid Beta-(m-Hydroxyphenyl)propionate Beta-(m-Hydroxyphenyl)propionic acid Dihydro-3-coumarate Dihydro-3-coumaric acid Dihydro-m-coumarate Dihydro-m-coumaric acid m-Hydrocoumarate M-hydrocoumaric acid M-Hydroxy-hydrocinnamate M-Hydroxy-Hydrocinnamic acid M-Hydroxyphenylpropionate M-Hydroxyphenylpropionic acid MHP β-(3-Hydroxyphenyl)propionate β-(3-Hydroxyphenyl)propionic acid β-(m-Hydroxyphenyl)propionate β-(m-Hydroxyphenyl)propionic acid C9H9O3 165.166 165.055169154 3-(2-carboxyethyl)benzen-1-olate 3-(2-carboxyethyl)benzenolate 621-54-5 OC(=O)CCC1=CC([O-])=CC=C1 InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)/p-1 QVWAEZJXDYOKEH-UHFFFAOYSA-M Solid Outer membrane Inner membrane logp 1.03 ALOGPS logs -1.37 ALOGPS solubility 7.76e+00 g/l ALOGPS logp 1.75 ChemAxon pka_strongest_acidic 4.21 ChemAxon pka_strongest_basic -6 ChemAxon iupac 3-(2-carboxyethyl)benzen-1-olate ChemAxon average_mass 165.166 ChemAxon mono_mass 165.055169154 ChemAxon smiles OC(=O)CCC1=CC([O-])=CC=C1 ChemAxon formula C9H9O3 ChemAxon inchi InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)/p-1 ChemAxon inchikey QVWAEZJXDYOKEH-UHFFFAOYSA-M ChemAxon polar_surface_area 60.36 ChemAxon refractivity 54.5 ChemAxon polarizability 16.53 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 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::NmrOneD 345548 Specdb::NmrOneD 345549 Specdb::NmrOneD 345550 Specdb::NmrOneD 345551 Specdb::NmrOneD 345552 Specdb::NmrOneD 345553 Specdb::NmrOneD 345554 Specdb::NmrOneD 345555 Specdb::NmrOneD 345556 Specdb::NmrOneD 345557 Specdb::NmrOneD 345558 Specdb::NmrOneD 345559 Specdb::NmrOneD 345560 Specdb::NmrOneD 345561 Specdb::NmrOneD 345562 Specdb::NmrOneD 345563 Specdb::NmrOneD 345564 Specdb::NmrOneD 345565 Specdb::NmrOneD 345566 Specdb::NmrOneD 345567 Specdb::MsMs 24632 Specdb::MsMs 24633 Specdb::MsMs 24634 Specdb::MsMs 31190 Specdb::MsMs 31191 Specdb::MsMs 31192 HMDB00375 6931501 5305660 C11457 1427 3-HYDROXYPHENYL-PROPIONATE 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 Rios, L. Y., Gonthier, M. P., Remesy, C., Mila, I., Lapierre, C., Lazarus, S. A., Williamson, G., Scalbert, A. (2003). "Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects." Am J Clin Nutr 77:912-918. 12663291 Konishi, Y., Kobayashi, S. (2004). "Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers." J Agric Food Chem 52:6418-6424. 15479001 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase P77397 MHPA_ECOLI mhpA http://ecmdb.ca/proteins/P77397.xml Putative 3-hydroxyphenylpropionic acid transporter P77589 MHPT_ECOLI mhpT http://ecmdb.ca/proteins/P77589.xml Hydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NAD MHPHYDROXY-RXN