2.0 2012-05-31 13:44:35 -0600 2015-06-03 15:53:42 -0600 ECMDB01072 M2MDB000242 Ubiquinone-10 Ubiquinone-10 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-10 has 10 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-10 is an extended version of Ubiquinone 8 that arises from conjugation by an extended 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. (all-E)-2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-Cyclohexadiene-1,4-dione (all-E)-2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-Cyclohexadiene-1,4-dione 2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-Benzoquinone 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-Cyclohexadiene-1,4-dione 4-Ethyl-5-fluoropyrimidine Aqua Q 10L10 Aqua Q10 Bio-Quinon Bio-Quinone Q10 Coenzyme Q10 Coenzyme-Q10 Coenzyme-Q<SUB>10</SUB> CoQ10 Ensorb Kaneka Q10 Kudesan Li-Q-Sorb Liquid-Q Neuquinon Neuquinone PureSorb Q 40 Q 10AA Q-Gel Q-Gel 100 Ubidecarenone Ubiquinone 10 Ubiquinone 50 Ubiquinone Q10 Ubiquinone(10) Ubiquinone-10 Unbiquinone Unispheres Q 10 C59H90O4 863.3435 862.683911368 2-[(2E,6E,10E,14E,18E,22E,26Z,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione ubisemiquinone 303-98-0 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)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ ACTIUHUUMQJHFO-UPTCCGCDSA-N Solid Inner membrane Membrane Outer membrane logp 9.94 ALOGPS logs -6.65 ALOGPS solubility 1.93e-04 g/l ALOGPS logp 17.16 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2-[(2E,6E,10E,14E,18E,22E,26Z,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 863.3435 ChemAxon mono_mass 862.683911368 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)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ChemAxon formula C59H90O4 ChemAxon inchi InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ ChemAxon inchikey ACTIUHUUMQJHFO-UPTCCGCDSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 286.61 ChemAxon polarizability 111.43 ChemAxon rotatable_bond_count 31 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon TCA cycle (ubiquinol-10) 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. PW001010 Metabolic Specdb::NmrOneD 303351 Specdb::NmrOneD 303352 Specdb::NmrOneD 303353 Specdb::NmrOneD 303354 Specdb::NmrOneD 303355 Specdb::NmrOneD 303356 Specdb::NmrOneD 303357 Specdb::NmrOneD 303358 Specdb::NmrOneD 303359 Specdb::NmrOneD 303360 Specdb::NmrOneD 303361 Specdb::NmrOneD 303362 Specdb::NmrOneD 303363 Specdb::NmrOneD 303364 Specdb::NmrOneD 303365 Specdb::NmrOneD 303366 Specdb::NmrOneD 303367 Specdb::NmrOneD 303368 Specdb::NmrOneD 303369 Specdb::NmrOneD 303370 Specdb::MsMs 301108 Specdb::MsMs 301109 Specdb::MsMs 301110 Specdb::MsMs 343549 Specdb::MsMs 343550 Specdb::MsMs 343551 HMDB01072 1156 4445197 C11378 UBIQUINONE-10 U10 coenzyme Q10 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). 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Journal of Micro 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 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 Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml Succinate dehydrogenase cytochrome b556 subunit P69054 DHSC_ECOLI sdhC http://ecmdb.ca/proteins/P69054.xml D-Glucose + Ubiquinone-10 > Gluconolactone + Ubiquinol-1 Pyruvic acid + Ubiquinone-10 + Water > Acetic acid + Carbon dioxide + Ubiquinol-1 Succinic acid + Ubiquinone-10 + FAD <> Fumaric acid + QH2 + FADH2 PW_R002582 Succinic acid + Ubiquinone-10 > Fumaric acid + Ubiquinol-10 + Ubiquinol-10 PW_R003753