2.0 2012-07-30 14:55:15 -0600 2015-06-03 17:21:06 -0600 ECMDB21296 M2MDB001700 Ubiquinone-8 Ubiquinone-8 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-8 has isoprene units. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. 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. 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]-1,4-benzoquinone Coenzyme Q8 Coenzyme-Q8 Coenzyme-Q<SUB>8</SUB> COQ8 Ubiquinone 8 Ubiquinone(8) Ubiquinone-8 C49H74O4 727.1095 726.558710856 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-dione ubiquinone 8 2394-68-5 COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O InChI=1S/C49H74O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+ ICFIZJQGJAJRSU-SGHXUWJISA-N Membrane logp 9.39 ALOGPS logs -6.49 ALOGPS solubility 2.38e-04 g/l ALOGPS logp 13.84 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 727.1095 ChemAxon mono_mass 726.558710856 ChemAxon smiles COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ChemAxon formula C49H74O4 ChemAxon inchi InChI=1S/C49H74O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+ ChemAxon inchikey ICFIZJQGJAJRSU-SGHXUWJISA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 239 ChemAxon polarizability 93.25 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon TCA cycle (ubiquinol-8) 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. PW001008 Metabolic Specdb::MsMs 38309 Specdb::MsMs 38310 Specdb::MsMs 38311 Specdb::MsMs 40757 Specdb::MsMs 40758 Specdb::MsMs 40759 Specdb::MsMs 3609058 Specdb::MsMs 3609059 Specdb::MsMs 3609060 Specdb::MsMs 3609061 Specdb::MsMs 3609062 Specdb::MsMs 3609063 5283546 4446659 C17569 61683 UBIQUINONE-8 UQ8 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 NADH dehydrogenase P00393 DHNA_ECOLI ndh http://ecmdb.ca/proteins/P00393.xml D-lactate dehydrogenase P06149 DLD_ECOLI dld http://ecmdb.ca/proteins/P06149.xml Pyruvate dehydrogenase [cytochrome] P07003 POXB_ECOLI poxB http://ecmdb.ca/proteins/P07003.xml Succinate dehydrogenase iron-sulfur subunit P07014 DHSB_ECOLI sdhB http://ecmdb.ca/proteins/P07014.xml Respiratory nitrate reductase 1 alpha chain P09152 NARG_ECOLI narG http://ecmdb.ca/proteins/P09152.xml Dihydroorotate dehydrogenase P0A7E1 PYRD_ECOLI pyrD http://ecmdb.ca/proteins/P0A7E1.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit C P0A996 GLPC_ECOLI glpC http://ecmdb.ca/proteins/P0A996.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit A P0A9C0 GLPA_ECOLI glpA http://ecmdb.ca/proteins/P0A9C0.xml Formate dehydrogenase, nitrate-inducible, iron-sulfur subunit P0AAJ3 FDNH_ECOLI fdnH http://ecmdb.ca/proteins/P0AAJ3.xml Formate dehydrogenase-O iron-sulfur subunit P0AAJ5 FDOH_ECOLI fdoH http://ecmdb.ca/proteins/P0AAJ5.xml Formate hydrogenlyase subunit 2 P0AAK1 HYCB_ECOLI hycB http://ecmdb.ca/proteins/P0AAK1.xml Cytochrome c-552 P0ABK9 NRFA_ECOLI nrfA http://ecmdb.ca/proteins/P0ABK9.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 Hydrogenase-1 large chain P0ACD8 MBHL_ECOLI hyaB http://ecmdb.ca/proteins/P0ACD8.xml Hydrogenase-2 large chain P0ACE0 MBHM_ECOLI hybC http://ecmdb.ca/proteins/P0ACE0.xml Probable quinol monooxygenase ygiN P0ADU2 YGIN_ECOLI ygiN http://ecmdb.ca/proteins/P0ADU2.xml Formate dehydrogenase, nitrate-inducible, cytochrome b556(fdn) subunit P0AEK7 FDNI_ECOLI fdnI http://ecmdb.ca/proteins/P0AEK7.xml Formate dehydrogenase, cytochrome b556(fdo) subunit P0AEL0 FDOI_ECOLI fdoI http://ecmdb.ca/proteins/P0AEL0.xml Glycolate oxidase subunit glcD P0AEP9 GLCD_ECOLI glcD http://ecmdb.ca/proteins/P0AEP9.xml Respiratory nitrate reductase 2 gamma chain P0AF32 NARV_ECOLI narV http://ecmdb.ca/proteins/P0AF32.xml NADH-quinone oxidoreductase subunit A P0AFC3 NUOA_ECOLI nuoA http://ecmdb.ca/proteins/P0AFC3.xml NADH-quinone oxidoreductase subunit B P0AFC7 NUOB_ECOLI nuoB http://ecmdb.ca/proteins/P0AFC7.xml NADH-quinone oxidoreductase subunit E P0AFD1 NUOE_ECOLI nuoE http://ecmdb.ca/proteins/P0AFD1.xml NADH-quinone oxidoreductase subunit H P0AFD4 NUOH_ECOLI nuoH http://ecmdb.ca/proteins/P0AFD4.xml NADH-quinone oxidoreductase subunit I P0AFD6 NUOI_ECOLI nuoI http://ecmdb.ca/proteins/P0AFD6.xml NADH-quinone oxidoreductase subunit J P0AFE0 NUOJ_ECOLI nuoJ http://ecmdb.ca/proteins/P0AFE0.xml NADH-quinone oxidoreductase subunit K P0AFE4 NUOK_ECOLI nuoK http://ecmdb.ca/proteins/P0AFE4.xml NADH-quinone oxidoreductase subunit M P0AFE8 NUOM_ECOLI nuoM http://ecmdb.ca/proteins/P0AFE8.xml NADH-quinone oxidoreductase subunit N P0AFF0 NUON_ECOLI nuoN http://ecmdb.ca/proteins/P0AFF0.xml L-aspartate oxidase P10902 NADB_ECOLI nadB http://ecmdb.ca/proteins/P10902.xml Respiratory nitrate reductase 1 beta chain P11349 NARH_ECOLI narH http://ecmdb.ca/proteins/P11349.xml Respiratory nitrate reductase 1 gamma chain P11350 NARI_ECOLI narI http://ecmdb.ca/proteins/P11350.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit B P13033 GLPB_ECOLI glpB http://ecmdb.ca/proteins/P13033.xml Aerobic glycerol-3-phosphate dehydrogenase P13035 GLPD_ECOLI glpD http://ecmdb.ca/proteins/P13035.xml Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml Formate hydrogenlyase subunit 5 P16431 HYCE_ECOLI hycE http://ecmdb.ca/proteins/P16431.xml Formate hydrogenlyase subunit 6 P16432 HYCF_ECOLI hycF http://ecmdb.ca/proteins/P16432.xml Formate hydrogenlyase subunit 7 P16433 HYCG_ECOLI hycG http://ecmdb.ca/proteins/P16433.xml 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.xml Probable nitrate reductase molybdenum cofactor assembly chaperone NarW P19317 NARW_ECOLI narW http://ecmdb.ca/proteins/P19317.xml Respiratory nitrate reductase 2 beta chain P19318 NARY_ECOLI narY http://ecmdb.ca/proteins/P19318.xml Respiratory nitrate reductase 2 alpha chain P19319 NARZ_ECOLI narZ http://ecmdb.ca/proteins/P19319.xml Formate dehydrogenase, nitrate-inducible, major subunit P24183 FDNG_ECOLI fdnG http://ecmdb.ca/proteins/P24183.xml NADH-quinone oxidoreductase subunit F P31979 NUOF_ECOLI nuoF http://ecmdb.ca/proteins/P31979.xml Formate dehydrogenase-O major subunit P32176 FDOG_ECOLI fdoG http://ecmdb.ca/proteins/P32176.xml L-lactate dehydrogenase [cytochrome] P33232 LLDD_ECOLI lldD http://ecmdb.ca/proteins/P33232.xml NADH-quinone oxidoreductase subunit C/D P33599 NUOCD_ECOLI nuoC http://ecmdb.ca/proteins/P33599.xml NADH-quinone oxidoreductase subunit G P33602 NUOG_ECOLI nuoG http://ecmdb.ca/proteins/P33602.xml NADH-quinone oxidoreductase subunit L P33607 NUOL_ECOLI nuoL http://ecmdb.ca/proteins/P33607.xml Periplasmic nitrate reductase P33937 NAPA_ECOLI napA http://ecmdb.ca/proteins/P33937.xml Malate:quinone oxidoreductase P33940 MQO_ECOLI mqo http://ecmdb.ca/proteins/P33940.xml Glycolate oxidase iron-sulfur subunit P52074 GLCF_ECOLI glcF http://ecmdb.ca/proteins/P52074.xml Succinate dehydrogenase cytochrome b556 subunit P69054 DHSC_ECOLI sdhC http://ecmdb.ca/proteins/P69054.xml Hydrogenase-1 small chain P69739 MBHS_ECOLI hyaA http://ecmdb.ca/proteins/P69739.xml Hydrogenase-2 small chain P69741 MBHT_ECOLI hybO http://ecmdb.ca/proteins/P69741.xml Ferredoxin-type protein napG P0AAL3 NAPG_ECOLI napG http://ecmdb.ca/proteins/P0AAL3.xml Modulator of drug activity B P0AEY5 MDAB_ECOLI mdaB http://ecmdb.ca/proteins/P0AEY5.xml Uncharacterized protein ykgE P77252 YKGE_ECOLI ykgE http://ecmdb.ca/proteins/P77252.xml Ferredoxin-type protein napH P33934 NAPH_ECOLI napH http://ecmdb.ca/proteins/P33934.xml Ubiquinol oxidase subunit 2 P0ABJ1 CYOA_ECOLI cyoA http://ecmdb.ca/proteins/P0ABJ1.xml Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit P0AAM1 CYBH_ECOLI hyaC http://ecmdb.ca/proteins/P0AAM1.xml Uncharacterized protein ykgG P77433 YKGG_ECOLI ykgG http://ecmdb.ca/proteins/P77433.xml Glycolate oxidase subunit glcE P52073 GLCE_ECOLI glcE http://ecmdb.ca/proteins/P52073.xml Cytochrome o ubiquinol oxidase protein cyoD P0ABJ6 CYOD_ECOLI cyoD http://ecmdb.ca/proteins/P0ABJ6.xml Thiol:disulfide interchange protein dsbA P0AEG4 DSBA_ECOLI dsbA http://ecmdb.ca/proteins/P0AEG4.xml Hydrogenase-2 operon protein hybA P0AAJ8 HYBA_ECOLI hybA http://ecmdb.ca/proteins/P0AAJ8.xml Uncharacterized electron transport protein ykgF P77536 YKGF_ECOLI ykgF http://ecmdb.ca/proteins/P77536.xml Cytochrome bd-II oxidase subunit 2 P26458 APPB_ECOLI appB http://ecmdb.ca/proteins/P26458.xml Protein nrfD P32709 NRFD_ECOLI nrfD http://ecmdb.ca/proteins/P32709.xml Probable Ni/Fe-hydrogenase 2 b-type cytochrome subunit P37180 HYBB_ECOLI hybB http://ecmdb.ca/proteins/P37180.xml Cytochrome bd-II oxidase subunit 1 P26459 APPC_ECOLI appC http://ecmdb.ca/proteins/P26459.xml Protein nrfC P0AAK7 NRFC_ECOLI nrfC http://ecmdb.ca/proteins/P0AAK7.xml Cytochrome d ubiquinol oxidase subunit 2 P0ABK2 CYDB_ECOLI cydB http://ecmdb.ca/proteins/P0ABK2.xml Cytochrome c-type protein nrfB P0ABL1 NRFB_ECOLI nrfB http://ecmdb.ca/proteins/P0ABL1.xml Soluble aldose sugar dehydrogenase yliI P75804 YLII_ECOLI yliI http://ecmdb.ca/proteins/P75804.xml Diheme cytochrome c napB P0ABL3 NAPB_ECOLI napB http://ecmdb.ca/proteins/P0ABL3.xml Ubiquinol oxidase subunit 1 P0ABI8 CYOB_ECOLI cyoB http://ecmdb.ca/proteins/P0ABI8.xml Formate hydrogenlyase subunit 3 P16429 HYCC_ECOLI hycC http://ecmdb.ca/proteins/P16429.xml Disulfide bond formation protein B P0A6M2 DSBB_ECOLI dsbB http://ecmdb.ca/proteins/P0A6M2.xml Cytochrome d ubiquinol oxidase subunit 1 P0ABJ9 CYDA_ECOLI cydA http://ecmdb.ca/proteins/P0ABJ9.xml Cytochrome c-type protein napC P0ABL5 NAPC_ECOLI napC http://ecmdb.ca/proteins/P0ABL5.xml Cytochrome o ubiquinol oxidase subunit 3 P0ABJ3 CYOC_ECOLI cyoC http://ecmdb.ca/proteins/P0ABJ3.xml Nitrate reductase molybdenum cofactor assembly chaperone NarJ P0AF26 NARJ_ECOLI narJ http://ecmdb.ca/proteins/P0AF26.xml Formate hydrogenlyase subunit 4 P16430 HYCD_ECOLI hycD http://ecmdb.ca/proteins/P16430.xml 2 Hydrogen ion + Hydrogen (gas) + Ubiquinone-8 > Ubiquinol-8 +2 Hydrogen ion 2 Hydrogen ion + Oxygen + Ubiquinol-8 > Water + Ubiquinone-8 +2 Hydrogen ion 2 Hydrogen ion + Nitrate + Ubiquinol-8 > Water + Nitrite + Ubiquinone-8 +2 Hydrogen ion Ubiquinol-8 + Nitrate > Ubiquinone-8 + Water + Nitrite Glycerol 3-phosphate + Ubiquinone-8 > Dihydroxyacetone phosphate + Ubiquinol-8 2 Hydrogen ion + Ubiquinone-8 + Formic acid > Ubiquinol-8 + Carbon dioxide + Hydrogen ion Ubiquinone-8 + D-Glucose + Water > Ubiquinol-8 + Gluconic acid + Hydrogen ion 4 Hydrogen ion + Oxygen + Ubiquinol-8 > Water + Ubiquinone-8 +4 Hydrogen ion Ubiquinone-8 + Succinic acid > Fumaric acid + Ubiquinol-8 4 Hydrogen ion + NADH + Ubiquinone-8 > NAD + Ubiquinol-8 +3 Hydrogen ion Glycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8 L-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8 Ubiquinone-8 + periplasmic protein disulfide isomerase I (reduced) > Ubiquinol-8 + periplasmic protein disulfide isomerase I (oxidized) 3 Ubiquinol-8 + 2 Hydrogen ion + Nitrite >3 Ubiquinone-8 +2 Water + Ammonium Water + Pyruvic acid + Ubiquinone-8 > Acetic acid + Carbon dioxide + Ubiquinol-8 4,5-Dihydroorotic acid + Ubiquinone-8 > Orotic acid + Ubiquinol-8 Hydrogen ion + NADH + Ubiquinone-8 > NAD + Ubiquinol-8 D-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8 L-Malic acid + Ubiquinone-8 > Oxalacetic acid + Ubiquinol-8 L-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8 Hydrogen ion + NADPH + Ubiquinone-8 > NADP + Ubiquinol-8 2 Oxygen + Ubiquinol-8 >2 Hydrogen ion +2 Superoxide anion + Ubiquinone-8 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> Ubiquinone-8 + S-Adenosylhomocysteine R05614 Ubiquinone-8 + Hydrogen ion > Ubiquinol-8 RXN0-5309 Ubiquinol-8 + Oxygen > Ubiquinone-8 + Water Succinic acid + Ubiquinone-8 > Fumaric acid + Ubiquinol 8 + Ubiquinol-8 PW_R003751