2.0 2012-05-31 14:25:34 -0600 2015-06-03 17:19:14 -0600 ECMDB20064 M2MDB000913 3-(2,3-Dihydroxyphenyl)propanoate 3-(2,3-dihydroxyphenyl)propanoate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propanoate is invovled in 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) (3R)-3-(2,4-dimethoxyphenyl)chroman-7-ol 2,3-Dhppa 2,3-DIHYDROXY-b-phenylproprionate 2,3-DIHYDROXY-B-PHENYLPROPRIONIC ACID 2,3-Dihydroxy-Benzenepropanoate 2,3-Dihydroxy-Benzenepropanoic acid 2,3-Dihydroxyphenylpropanoate 2,3-Dihydroxyphenylpropanoic acid 2,3-Dihydroxyphenylpropionate 2,3-Dihydroxyphenylpropionic acid 2-3-DIHYDROXYPHENYL-PROPIONATE 2-3-DIHYDROXYPHENYL-propionic acid 3,4-Dihydroxy-Benzenepropanoate 3,4-Dihydroxy-Benzenepropanoic acid 3,4-Dihydroxy-Hydrocinnamate 3,4-Dihydroxy-Hydrocinnamic acid 3,4-Dihydroxybenzenepropanoate 3,4-Dihydroxybenzenepropanoic acid 3,4-Dihydroxyhydrocinnamate 3,4-Dihydroxyhydrocinnamic acid 3,4-Dihydroxyphenylpropionate 3,4-Dihydroxyphenylpropionic acid 3-(2,3-Dihydroxyphenyl)propanoate 3-(2,3-Dihydroxyphenyl)propanoic acid 3-(2,3-Dihydroxyphenyl)propionate 3-(2,3-Dihydroxyphenyl)propionic acid 3-(3,4-Dihydroxyphenyl)propionate 3-(3,4-Dihydroxyphenyl)propionic acid Benzenepropanoate, 3,4-dihydroxy- (9CI) Benzenepropanoic acid, 3,4-dihydroxy- (9CI) Dihydrocaffeate Dihydrocaffeic acid Hydrocaffeate Hydrocaffeic acid C9H10O4 182.1733 182.057908808 3-(2,3-dihydroxyphenyl)propanoic acid 2,3-dhppa 3714-73-6 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) QZDSXQJWBGMRLU-UHFFFAOYSA-N Outer membrane Inner membrane logp 1.04 ALOGPS logs -1.78 ALOGPS solubility 3.02e+00 g/l ALOGPS logp 1.45 ChemAxon pka_strongest_acidic 3.84 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 3-(2,3-dihydroxyphenyl)propanoic acid ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles OC(=O)CCC1=C(O)C(O)=CC=C1 ChemAxon formula C9H10O4 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) ChemAxon inchikey QZDSXQJWBGMRLU-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 45.93 ChemAxon polarizability 17.68 ChemAxon rotatable_bond_count 3 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 Specdb::CMs 55700 Specdb::CMs 57534 Specdb::CMs 174140 Specdb::NmrOneD 262208 Specdb::NmrOneD 262209 Specdb::NmrOneD 262210 Specdb::NmrOneD 262211 Specdb::NmrOneD 262212 Specdb::NmrOneD 262213 Specdb::NmrOneD 262214 Specdb::NmrOneD 262215 Specdb::NmrOneD 262216 Specdb::NmrOneD 262217 Specdb::NmrOneD 262218 Specdb::NmrOneD 262219 Specdb::NmrOneD 262220 Specdb::NmrOneD 262221 Specdb::NmrOneD 262222 Specdb::NmrOneD 262223 Specdb::NmrOneD 262224 Specdb::NmrOneD 262225 Specdb::NmrOneD 262226 Specdb::NmrOneD 262227 Specdb::MsMs 27734 Specdb::MsMs 27735 Specdb::MsMs 27736 Specdb::MsMs 34292 Specdb::MsMs 34293 Specdb::MsMs 34294 Specdb::MsMs 2372058 Specdb::MsMs 2372059 Specdb::MsMs 2372060 Specdb::MsMs 2563197 Specdb::MsMs 2563198 Specdb::MsMs 2563199 20 19 C04044 18136 CPD-9367 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 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 cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propanoate + NADH 3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD 3-(2,3-Dihydroxyphenyl)propanoate + Oxygen > 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioate