2.0 2012-05-31 14:03:57 -0600 2015-06-03 15:54:41 -0600 ECMDB04061 M2MDB000591 3-(2,3-Dihydroxyphenyl)propionic acid 3-(2,3-dihydroxyphenyl)propionate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propionate is invovled in Phenylalanine metabolism, Microbial metabolism in diverse environments, and Phenylpropionic acid degradation. The compound 3-(2,3-dihydroxyphenyl)propionate (DHPP) is a common intermediate of both pathways which must be cleaved by the MhpB dioxygenase before entering into the primary cell metabolism. (PMID 19520845) 2,3-DHP 2,3-Dihydroxyphenylpropanoate 2,3-Dihydroxyphenylpropanoic acid 3-(2,3-Dihydroxyphenyl)propanoate 3-(2,3-Dihydroxyphenyl)propanoic acid 3-(2,3-Dihydroxyphenyl)propionate 3-(2,3-Dihydroxyphenyl)propionic acid 3-(2,3-Hihydroxyphenyl)propanoate 3-(2,3-Hihydroxyphenyl)propanoic acid 3-Carboxyethylcatechol C9H9O4 181.1654 181.050083776 3-(2-carboxyethyl)-2-hydroxybenzen-1-olate 3-(2-carboxyethyl)-2-hydroxybenzenolate OC(=O)CCC1=C(O)C([O-])=CC=C1 InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)/p-1 QZDSXQJWBGMRLU-UHFFFAOYSA-M Cytosol logp 0.87 ALOGPS logs -1.11 ALOGPS solubility 1.55e+01 g/l ALOGPS logp 1.45 ChemAxon pka_strongest_acidic 3.84 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 3-(2-carboxyethyl)-2-hydroxybenzen-1-olate ChemAxon average_mass 181.1654 ChemAxon mono_mass 181.050083776 ChemAxon smiles OC(=O)CCC1=C(O)C([O-])=CC=C1 ChemAxon formula C9H9O4 ChemAxon inchi InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)/p-1 ChemAxon inchikey QZDSXQJWBGMRLU-UHFFFAOYSA-M ChemAxon polar_surface_area 80.59 ChemAxon refractivity 56.48 ChemAxon polarizability 17.31 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 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 2-Oxopent-4-enoate metabolism The 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 cycle PW001890 Metabolic 2-Oxopent-4-enoate metabolism 2 The 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 cycle PW002035 Metabolic 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY Specdb::NmrOneD 288655 Specdb::NmrOneD 288656 Specdb::NmrOneD 288657 Specdb::NmrOneD 288658 Specdb::NmrOneD 288659 Specdb::NmrOneD 288660 Specdb::NmrOneD 288661 Specdb::NmrOneD 288662 Specdb::NmrOneD 288663 Specdb::NmrOneD 288664 Specdb::NmrOneD 288665 Specdb::NmrOneD 288666 Specdb::NmrOneD 288667 Specdb::NmrOneD 288668 Specdb::NmrOneD 288669 Specdb::NmrOneD 288670 Specdb::NmrOneD 288671 Specdb::NmrOneD 288672 Specdb::NmrOneD 288673 Specdb::NmrOneD 288674 Specdb::MsMs 27842 Specdb::MsMs 27843 Specdb::MsMs 27844 Specdb::MsMs 34400 Specdb::MsMs 34401 Specdb::MsMs 34402 9543123 7822096 C04044 46951 2-3-DIHYDROXYPHENYL-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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Manso, I., Torres, B., Andreu, J. M., Menendez, M., Rivas, G., Alfonso, C., Diaz, E., Garcia, J. L., Galan, B. (2009). "3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli." J Biol Chem 284:21218-21228. 19520845 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase P0ABR9 MHPB_ECOLI mhpB http://ecmdb.ca/proteins/P0ABR9.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-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD R06786 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylate R04376 1.13.11.16-RXN Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylate R04376 cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion R06784 PHENPRODIOLDEHYDROG-RXN 3-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD R06786 Hydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NAD MHPHYDROXY-RXN cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > Hydrogen ion + 3-(2,3-Dihydroxyphenyl)propionic acid + NADH PHENPRODIOLDEHYDROG-RXN 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 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 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > (2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Hydrogen ion PW_R005882