2.0 2012-05-31 14:53:48 -0600 2015-09-17 15:41:50 -0600 ECMDB20620 M2MDB001418 Ubiquinone-6 Ubiquinone-6 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-6 has just 6 isoprene units. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-6 is a “failed” or incomplete version of Ubiquinone 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays 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. C9504_SIGMA Coenzyme Q6 Coenzyme Qq6 Coenzyme-?Q6 Coenzyme-Q6 Coenzyme-Q<SUB>6</SUB> CoQ-6 CoQ6 Q6 Ubiquinone 30 Ubiquinone 6 Ubiquinone Q6 Ubiquinone(30) Ubiquinone(6) Ubiquinone-30 C39H58O4 590.8754 590.433510344 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-methylcyclohexa-2,5-diene-1,4-dione ubiquinone 6 1065-31-2 COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O InChI=1S/C39H58O4/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/h16,18,20,22,24,26H,11-15,17,19,21,23,25,27H2,1-10H3 GXNFPEOUKFOTKY-UHFFFAOYSA-N Inner membrane Membrane Outer membrane logp 8.41 ALOGPS logs -6.26 ALOGPS solubility 3.25e-04 g/l ALOGPS logp 10.52 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-methylcyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 590.8754 ChemAxon mono_mass 590.433510344 ChemAxon smiles COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ChemAxon formula C39H58O4 ChemAxon inchi InChI=1S/C39H58O4/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/h16,18,20,22,24,26H,11-15,17,19,21,23,25,27H2,1-10H3 ChemAxon inchikey GXNFPEOUKFOTKY-UHFFFAOYSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 191.39 ChemAxon polarizability 73.44 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 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::NmrOneD 260568 Specdb::NmrOneD 260569 Specdb::NmrOneD 260570 Specdb::NmrOneD 260571 Specdb::NmrOneD 260572 Specdb::NmrOneD 260573 Specdb::NmrOneD 260574 Specdb::NmrOneD 260575 Specdb::NmrOneD 260576 Specdb::NmrOneD 260577 Specdb::NmrOneD 260578 Specdb::NmrOneD 260579 Specdb::NmrOneD 260580 Specdb::NmrOneD 260581 Specdb::NmrOneD 260582 Specdb::NmrOneD 260583 Specdb::NmrOneD 260584 Specdb::NmrOneD 260585 Specdb::NmrOneD 260586 Specdb::NmrOneD 260587 Specdb::MsMs 103914 Specdb::MsMs 103915 Specdb::MsMs 103916 Specdb::MsMs 170082 Specdb::MsMs 170083 Specdb::MsMs 170084 5283544 4446657 C17568 UBIQUINONE-6 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 Kanehisa, 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. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.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