2.02012-07-30 14:55:17 -06002015-06-03 17:21:09 -0600ECMDB21320M2MDB001722Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diolCis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is a member of the chemical class known as Cyclic Alcohols and Derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is invovled in Phenylpropionic acid degradation. r 15;80(8):2939-48.)3-(<i>cis</i>-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoic acid<i>cis</i>-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol<i>cis</i>-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diolCis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diolC9H11O4183.1812183.065733843-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate[H]O[C@]1([H])C([H])=C([H])C([H])=C(C([H])([H])C([H])([H])C([O-])=O)[C@]1([H])O[H]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)/p-1/t7-,9+/m1/s1RKDFGWAXBBGKMR-APPZFPTMSA-MCytoplasmlogp0.11logs-0.26solubility1.10e+02 g/llogp-0.39pka_strongest_acidic4.38pka_strongest_basic-3.3iupac3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoateaverage_mass183.1812mono_mass183.06573384smiles[H]O[C@]1([H])C([H])=C([H])C([H])=C(C([H])([H])C([H])([H])C([O-])=O)[C@]1([H])O[H]formulaC9H11O4inchiInChI=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)/p-1/t7-,9+/m1/s1inchikeyRKDFGWAXBBGKMR-APPZFPTMSA-Mpolar_surface_area80.59refractivity58.55polarizability17.77rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge-12-Oxopent-4-enoate metabolism 2The 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 cyclePW002035Metabolic3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoateHCAMHPDEG-PWYSpecdb::MsMs26159Specdb::MsMs26160Specdb::MsMs26161Specdb::MsMs32717Specdb::MsMs32718Specdb::MsMs3271995431277822100C11588CARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOLKeseler, 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-D590.210978823-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.xmlHydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NADCis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADHNADH + Oxygen + 3-phenylpropanoate <> NAD + Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diolPW_R003837trans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NADPW_R005945Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + NADH + Hydrogen ionPW_R005946