2.0 2012-08-09 09:25:33 -0600 2015-06-03 17:21:49 -0600 ECMDB21578 M2MDB001972 Ubiquinol-5 Ubiquinol-5 is a member of the chemical class known as Polyprenylbenzoquinols. They are reduced forms of polyprenylbenzoquinines (ubiquinones). These are compounds containing a polyisoprene chain attached to a quinol at the second ring position. Ubiquiol-5 has just 5 isoprene units. Normally in E. coli the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-5 is a “failed” or incomplete version of Ubiquinol 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Coenzyme Q(n) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinones or ubisemiquinones), and fully reduced (ubiquinols). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form. Ubiquionols are important in cellular respiration. They are fat-soluble and therefore mobile in cellular membranes; they play a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP. Not Available C34H52O4 524.7743 524.386560152 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]benzene-1,4-diol 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]benzene-1,4-diol COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC InChI=1S/C34H52O4/c1-24(2)14-10-15-25(3)16-11-17-26(4)18-12-19-27(5)20-13-21-28(6)22-23-30-29(7)31(35)33(37-8)34(38-9)32(30)36/h14,16,18,20,22,35-36H,10-13,15,17,19,21,23H2,1-9H3/b25-16+,26-18+,27-20+,28-22+ BJOPRJZXDVAPDG-UVCHAVPFSA-N Membrane logp 7.92 ALOGPS logs -6.05 ALOGPS solubility 4.64e-04 g/l ALOGPS logp 9.93 ChemAxon pka_strongest_acidic 10.27 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]benzene-1,4-diol ChemAxon average_mass 524.7743 ChemAxon mono_mass 524.386560152 ChemAxon smiles COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC ChemAxon formula C34H52O4 ChemAxon inchi InChI=1S/C34H52O4/c1-24(2)14-10-15-25(3)16-11-17-26(4)18-12-19-27(5)20-13-21-28(6)22-23-30-29(7)31(35)33(37-8)34(38-9)32(30)36/h14,16,18,20,22,35-36H,10-13,15,17,19,21,23H2,1-9H3/b25-16+,26-18+,27-20+,28-22+ ChemAxon inchikey BJOPRJZXDVAPDG-UVCHAVPFSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 167.44 ChemAxon polarizability 65.95 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon TCA cycle (ubiquinol-5) The TCA pathway is a catabolic pathway of aerobic respiration. It generates energy and reducing power. It is the first step in generating precursors for biosynthesis. When acetate is the carbon source, citrate synthase is rate-limiting for the TCA cycle. Respiration is an ATP-generating process in which compounds act as electron donors through a chain of electron transfer to electron acceptors. Aerobic respiration uses oxygen as the final acceptor. Anaerobic respiration uses several organic compounds as acceptors such as fumarate, nitrate and hydrogen. During the chain of electron transfer, protons (H+) are transported outside the cytoplasmic membrane, generating a proton motive force. Upon passage of protons back into the cytoplasm, the PMF energy is captured as ATP, catalyzed by a multisubunit ATPase. The cycle can start from Acetyl-CoA interacting with Oxalacetic acid and water through a citrate synthase monomer resulting in a hydrogen ion, CoA and a Citric Acid. The latter compound is dehydrated by a Citrate hydro-lyase resulting in the release of water and a cis-Aconitic acid. This compound is then hydrated through a Citrate hydro-lyase resulting in a D-threo-Isocitric acid. This compound is decarboxylated by an NADP dependent Citrate dehydrogenase, resulting in a release of carbon dioxide and NADPH and Oxoglutaric acid. The oxoglutaric acid interacts with a Coenzyme A through a NAD driven 2-oxoglutarate dehydrogenase resulting in a release of carbon dioxide, an NADH and succinyl-CoA. The succinyl-CoA interacts with a phosphate and an ADP through a 2-oxoglutarate dehydrogenase resulting in a CoA, an ATP and Succinic Acid. Succinic acid interacts with a ubiquinone, in this case a ubiquinone 1 through a succinate:quinone oxidoreductase resulting in an ubiquinol, in this case a ubiquinol-1 and a fumaric acid. The fumaric acid interacts with water through a fumarase hydratase resulting in a L-Malic acid.This compound can either interact with quinone through a malate:quinone oxidoreductase resulting in a release of hydroquinone and oxalacetic acid, or it can react with an NAD through a malate dehydrogenase resulting in a hydrogen ion, NADH and Oxalacetic acid. PW001005 Metabolic Specdb::CMs 1088451 Specdb::EiMs 5629 Specdb::MsMs 25922 Specdb::MsMs 25923 Specdb::MsMs 25924 Specdb::MsMs 32480 Specdb::MsMs 32481 Specdb::MsMs 32482 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 Succinate dehydrogenase iron-sulfur subunit P07014 DHSB_ECOLI sdhB http://ecmdb.ca/proteins/P07014.xml Succinate dehydrogenase flavoprotein subunit P0AC41 DHSA_ECOLI sdhA http://ecmdb.ca/proteins/P0AC41.xml Succinate dehydrogenase hydrophobic membrane anchor subunit P0AC44 DHSD_ECOLI sdhD http://ecmdb.ca/proteins/P0AC44.xml Succinate dehydrogenase cytochrome b556 subunit P69054 DHSC_ECOLI sdhC http://ecmdb.ca/proteins/P69054.xml Succinic acid + Ubiquinone-5 > Fumaric acid + Ubiquinol-5 PW_R003748