2.0 2012-05-31 14:47:17 -0600 2015-06-03 17:20:05 -0600 ECMDB20487 M2MDB001302 Ubiquinone-0 Ubiquinone-1 is a member of the chemical class known as Benzoquinones. 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 a naked 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. 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 2,3-Dimethoxy-5-methyl-2,5-Cyclohexadiene-1,4-dione 2,3-Dimethoxy-5-methyl-p-benzoquinone 2,3-Dimethoxy-5-methylbenzo-1,4-quinone 2,3-Dimethoxy-5-methylbenzoquinone 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione 2,3-Dimethyoxyl-5-methyl-1,4-benzoquinone 2-Methyl-4,5-dimethoxy-p-quinone 2-Methyl-5,6-dimethoxybenzoquinone Coenzyme q0 Coq0 D9150_SIGMA Nchembio.62-comp10 Q0 Q<SUB>0</SUB> Ubiquinone 0 Ubiquinone q0 Ubiquinone-O Ubiquinone-Q0 Ubiquinone-Q₀ C9H10O4 182.1733 182.057908808 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione coenzyme Q0 605-94-7 COC1=C(OC)C(=O)C(C)=CC1=O InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3 UIXPTCZPFCVOQF-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 0.53 ALOGPS logs -1.53 ALOGPS solubility 5.37e+00 g/l ALOGPS melting_point 59-60 oC logp 0.61 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles COC1=C(OC)C(=O)C(C)=CC1=O ChemAxon formula C9H10O4 ChemAxon inchi InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3 ChemAxon inchikey UIXPTCZPFCVOQF-UHFFFAOYSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 48.82 ChemAxon polarizability 17.64 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon TCA cycle (ubiquinol-0) 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. PW002023 Metabolic pyruvate to cytochrome bd terminal oxidase electron transfer The reaction of pyruvate to cytochrome bd terminal oxidase electron transfer starts with 2 pyruvate and 2 water molecules reacting in a pyruvate oxidase resulting in the release of 4 electrons into the inner membrane, and releasing 2 carbon dioxide molecules , 2 acetate and 4 hydrogen ion into the cytosol. 2 ubiquinone,4 hydrogen ion and 4 electron ion react resulting in the release of 2 ubiquinol . The 2 ubiquinol in turn release 4 hydrogen ions into the periplasmic space through a cytochrome bd-I terminal oxidase and releasing 4 electrons through the enzyme. Oxygen and 4 hydrogen ion reacts with the 4 electrons resulting in 2 water molecules. PW002087 Metabolic Specdb::EiMs 5443 Specdb::NmrOneD 344008 Specdb::NmrOneD 344009 Specdb::NmrOneD 344010 Specdb::NmrOneD 344011 Specdb::NmrOneD 344012 Specdb::NmrOneD 344013 Specdb::NmrOneD 344014 Specdb::NmrOneD 344015 Specdb::NmrOneD 344016 Specdb::NmrOneD 344017 Specdb::NmrOneD 344018 Specdb::NmrOneD 344019 Specdb::NmrOneD 344020 Specdb::NmrOneD 344021 Specdb::NmrOneD 344022 Specdb::NmrOneD 344023 Specdb::NmrOneD 344024 Specdb::NmrOneD 344025 Specdb::NmrOneD 344026 Specdb::NmrOneD 344027 Specdb::MsMs 27401 Specdb::MsMs 27402 Specdb::MsMs 27403 Specdb::MsMs 33959 Specdb::MsMs 33960 Specdb::MsMs 33961 69068 62289 C05251 27906 CPD0-1464 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 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 Succinate dehydrogenase cytochrome b556 subunit P69054 DHSC_ECOLI sdhC http://ecmdb.ca/proteins/P69054.xml Probable ubiquinone biosynthesis protein ubiB P0A6A0 UBIB_ECOLI ubiB http://ecmdb.ca/proteins/P0A6A0.xml Ubiquinone-0 + Succinic acid > Ubiquinol-0 + Fumaric acid PW_R005886