2.02012-05-31 14:29:01 -06002015-06-03 17:19:22 -0600ECMDB20129M2MDB000977cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diolCis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diol belongs to the class of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (inferred from compound structure)(2<i>E</i>)-3-[(5<i>R</i>,6<i>S</i>)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate(2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoate(2E)-3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid3-(<i>cis</i>-5,6-dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoic acid3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]acrylate3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]acrylic acid<i>cis</i>-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diolCis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diolC9H10O4182.1733182.057908808(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid[H]\C(=C(\[H])C1=CC=C[C@]([H])(O)[C@]1([H])O)C(O)=OInChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/b5-4+/t7-,9+/m0/s1AEUBLTTWYCDTGM-HXOXMVQHSA-NCytosollogp0.22logs-1.32solubility8.65e+00 g/llogp-0.4pka_strongest_acidic4.45pka_strongest_basic-3.3iupac(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acidaverage_mass182.1733mono_mass182.057908808smiles[H]\C(=C(\[H])C1=CC=C[C@]([H])(O)[C@]1([H])O)C(O)=OformulaC9H10O4inchiInChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/b5-4+/t7-,9+/m0/s1inchikeyAEUBLTTWYCDTGM-HXOXMVQHSA-Npolar_surface_area77.76refractivity48.8polarizability17.71rotatable_bond_count2acceptor_count4donor_count3physiological_charge-1formal_charge0Phenylalanine metabolismThe 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.PW000921ec00360MetabolicMicrobial metabolism in diverse environmentsec011202-Oxopent-4-enoate metabolismThe 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 cyclePW001890Metaboliccinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-6690Specdb::CMs1086087Specdb::NmrOneD308751Specdb::NmrOneD308752Specdb::NmrOneD308753Specdb::NmrOneD308754Specdb::NmrOneD308755Specdb::NmrOneD308756Specdb::NmrOneD308757Specdb::NmrOneD308758Specdb::NmrOneD308759Specdb::NmrOneD308760Specdb::NmrOneD308761Specdb::NmrOneD308762Specdb::NmrOneD308763Specdb::NmrOneD308764Specdb::NmrOneD308765Specdb::NmrOneD308766Specdb::NmrOneD308767Specdb::NmrOneD308768Specdb::NmrOneD308769Specdb::NmrOneD308770Specdb::MsMs29897Specdb::MsMs29898Specdb::MsMs29899Specdb::MsMs23099Specdb::MsMs23100Specdb::MsMs2310152821454445342C12622CPD-13034Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A3-phenylpropionate/cinnamic acid dioxygenase subunit alphaP0ABR5HCAE_ECOLIhcaEhttp://ecmdb.ca/proteins/P0ABR5.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunitP0ABW0HCAC_ECOLIhcaChttp://ecmdb.ca/proteins/P0ABW0.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase componentP77650HCAD_ECOLIhcaDhttp://ecmdb.ca/proteins/P77650.xml3-phenylpropionate/cinnamic acid dioxygenase subunit betaQ47140HCAF_ECOLIhcaFhttp://ecmdb.ca/proteins/Q47140.xml3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenaseP0CI31hcaBhttp://ecmdb.ca/proteins/P0CI31.xmltrans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR06783RXN-12072cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADHR06785RXN-12071trans-Cinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR06783cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD <> Trans-2,3-Dihydroxycinnamate + NADH + Hydrogen ionR06785cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADHcis-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-DihydroxycinnamateR06784 Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADPW_R003835NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol > NADH + Hydrogen ion + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidPW_R005157