2.0 2012-07-30 14:55:17 -0600 2015-06-03 17:21:09 -0600 ECMDB21320 M2MDB001722 Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol Cis-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-(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 cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol cis-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diol Cis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diol C9H11O4 183.1812 183.06573384 3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate 3-[(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/s1 RKDFGWAXBBGKMR-APPZFPTMSA-M Cytoplasm logp 0.11 ALOGPS logs -0.26 ALOGPS solubility 1.10e+02 g/l ALOGPS logp -0.39 ChemAxon pka_strongest_acidic 4.38 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate ChemAxon average_mass 183.1812 ChemAxon mono_mass 183.06573384 ChemAxon smiles [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] ChemAxon formula C9H11O4 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)/p-1/t7-,9+/m1/s1 ChemAxon inchikey RKDFGWAXBBGKMR-APPZFPTMSA-M ChemAxon polar_surface_area 80.59 ChemAxon refractivity 58.55 ChemAxon polarizability 17.77 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon 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::MsMs 26159 Specdb::MsMs 26160 Specdb::MsMs 26161 Specdb::MsMs 32717 Specdb::MsMs 32718 Specdb::MsMs 32719 9543127 7822100 C11588 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 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 Hydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH NADH + Oxygen + 3-phenylpropanoate <> NAD + Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol PW_R003837 trans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD PW_R005945 Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + NADH + Hydrogen ion PW_R005946