2.0 2012-08-09 09:16:19 -0600 2015-06-03 17:21:33 -0600 ECMDB21460 M2MDB001855 Ubiquinol-6 Ubiquinol-6 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-6 has just 6 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-6 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. 2-(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl-5,6-dimethoxy-3-methylbenzene-1,4-diol Dihydroubiquinone Reduced ubiquinone Ubiquinol Ubiquinol(30) C39H60O4 592.8913 592.449160408 2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol ubiquinol-6 5677-58-7 COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC InChI=1S/C39H60O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26,40-41H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+ DYOSCPIQEYRQEO-LPHQIWJTSA-N Solid Membrane logp 8.49 ALOGPS logs -6.23 ALOGPS solubility 3.49e-04 g/l ALOGPS logp 11.59 ChemAxon pka_strongest_acidic 10.27 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol ChemAxon average_mass 592.8913 ChemAxon mono_mass 592.449160408 ChemAxon smiles COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC ChemAxon formula C39H60O4 ChemAxon inchi InChI=1S/C39H60O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26,40-41H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+ ChemAxon inchikey DYOSCPIQEYRQEO-LPHQIWJTSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 191.24 ChemAxon polarizability 75.45 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon TCA cycle (ubiquinol-6) 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. PW001006 Metabolic Specdb::CMs 25498 Specdb::CMs 39903 Specdb::CMs 282919 Specdb::CMs 424707 Specdb::CMs 424708 Specdb::CMs 424709 Specdb::CMs 424710 Specdb::CMs 424711 Specdb::NmrOneD 320471 Specdb::NmrOneD 320472 Specdb::NmrOneD 320473 Specdb::NmrOneD 320474 Specdb::NmrOneD 320475 Specdb::NmrOneD 320476 Specdb::NmrOneD 320477 Specdb::NmrOneD 320478 Specdb::NmrOneD 320479 Specdb::NmrOneD 320480 Specdb::NmrOneD 320481 Specdb::NmrOneD 320482 Specdb::NmrOneD 320483 Specdb::NmrOneD 320484 Specdb::NmrOneD 320485 Specdb::NmrOneD 320486 Specdb::NmrOneD 320487 Specdb::NmrOneD 320488 Specdb::NmrOneD 320489 Specdb::NmrOneD 320490 Specdb::MsMs 28298 Specdb::MsMs 28299 Specdb::MsMs 28300 Specdb::MsMs 34856 Specdb::MsMs 34857 Specdb::MsMs 34858 Specdb::MsMs 2395581 Specdb::MsMs 2395582 Specdb::MsMs 2395583 Specdb::MsMs 2539295 Specdb::MsMs 2539296 Specdb::MsMs 2539297 HMDB12299 3393375 52970 NULL 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 D-lactate dehydrogenase P06149 DLD_ECOLI dld http://ecmdb.ca/proteins/P06149.xml 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-6 > Fumaric acid + Ubiquinol-6 PW_R003749 L-Lactic acid + Ubiquinone-6 > Pyruvic acid + Ubiquinol-6 PW_R006151