2.0 2012-05-31 14:29:05 -0600 2015-06-03 17:19:22 -0600 ECMDB20130 M2MDB000978 cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol Cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol (also known as 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate) is an intermediate invovled in Phenylpropionic acid degradation. It is a substrate for the enzyme 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase (hcaB). This enzyme normally converts 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol) into 3-(2,3-dihydroxylphenyl)propanoic acid (DHPP) and 2,3-dihydroxicinnamic acid (DHCI), respectively. Cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol is also a substrate for 3-phenylpropionate/cinnamic acid dioxygenase (hcaE and hcaF), which is also part of the phentylpropionic acid degradatioin pathway. This enzyme catalyzes the reaction 3-phenylpropanoate + NADH + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+ 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoic acid 3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoate 3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoic acid cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol cis-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diol Cis-3-(2-Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol Cis-3-(2-Carboxyethyl)-3,5-cyclohexadiene-1,2-diol Cis-3-(3-Carboxyethyl)-3,5-cyclohexadiene-1,2-diol Cis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diol C9H12O4 184.1892 184.073558872 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid [H][C@]1(O)C=CC=C(CCC(O)=O)[C@@]1([H])O InChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/t7-,9+/m0/s1 RKDFGWAXBBGKMR-IONNQARKSA-N Cytosol logp -0.14 ALOGPS logs -0.74 ALOGPS solubility 3.36e+01 g/l ALOGPS logp -0.39 ChemAxon pka_strongest_acidic 4.38 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid ChemAxon average_mass 184.1892 ChemAxon mono_mass 184.073558872 ChemAxon smiles [H][C@]1(O)C=CC=C(CCC(O)=O)[C@@]1([H])O ChemAxon formula C9H12O4 ChemAxon inchi InChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/t7-,9+/m0/s1 ChemAxon inchikey RKDFGWAXBBGKMR-IONNQARKSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 47.71 ChemAxon polarizability 18.16 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 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY Specdb::CMs 1084302 Specdb::EiMs 2680 Specdb::NmrOneD 314581 Specdb::NmrOneD 314582 Specdb::NmrOneD 314583 Specdb::NmrOneD 314584 Specdb::NmrOneD 314585 Specdb::NmrOneD 314586 Specdb::NmrOneD 314587 Specdb::NmrOneD 314588 Specdb::NmrOneD 314589 Specdb::NmrOneD 314590 Specdb::NmrOneD 314591 Specdb::NmrOneD 314592 Specdb::NmrOneD 314593 Specdb::NmrOneD 314594 Specdb::NmrOneD 314595 Specdb::NmrOneD 314596 Specdb::NmrOneD 314597 Specdb::NmrOneD 314598 Specdb::NmrOneD 314599 Specdb::NmrOneD 314600 Specdb::MsMs 25754 Specdb::MsMs 25755 Specdb::MsMs 25756 Specdb::MsMs 32312 Specdb::MsMs 32313 Specdb::MsMs 32314 443290 391536 C11588 10472 CARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOL 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 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 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A 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 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase P0CI31 hcaB http://ecmdb.ca/proteins/P0CI31.xml Hydrocinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD R06782 HCAMULTI-RXN cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion R06784 PHENPRODIOLDEHYDROG-RXN Hydrocinnamic acid + NADH + Oxygen + Hydrogen ion > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD HCAMULTI-RXN cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > Hydrogen ion + 3-(2,3-Dihydroxyphenyl)propionic acid + NADH PHENPRODIOLDEHYDROG-RXN cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propanoate + NADH 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 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 NADH + Oxygen + 3-phenylpropanoate <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol PW_R003836 Hydrocinnamic acid + NADH + Oxygen <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol PW_R003850