2.0 2012-08-09 09:25:34 -0600 2015-06-03 17:21:50 -0600 ECMDB21583 M2MDB001977 Ubiquinone-9 Ubiquinone-9 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-9 has 9 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-9 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-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl)-2,5-cyclohexadiene-1,4-dione 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]-1,4-benzoquinone 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]cyclohexa-2,5-diene-1,4-dione 2-Methyl-3-nonaprenyl-5,6-dimethoxy-1,4-benzoquinone Coenzyme Q(9) Coenzyme Q(sub 9) Coenzyme Q9 CoQ(sub 9) CoQ9 Ubiquinone 45 Ubiquinone 9 Ubiquinone Q(sub 9) Ubiquinone Q9 Ubiquinone-45 Ubiquinone-9 C54H82O4 795.2265 794.621311112 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]cyclohexa-2,5-diene-1,4-dione ubiquinone 9 303-97-9 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)CCC=C(C)C)=C(C)C1=O InChI=1S/C54H82O4/c1-40(2)22-14-23-41(3)24-15-25-42(4)26-16-27-43(5)28-17-29-44(6)30-18-31-45(7)32-19-33-46(8)34-20-35-47(9)36-21-37-48(10)38-39-50-49(11)51(55)53(57-12)54(58-13)52(50)56/h22,24,26,28,30,32,34,36,38H,14-21,23,25,27,29,31,33,35,37,39H2,1-13H3/b41-24+,42-26+,43-28+,44-30+,45-32+,46-34+,47-36+,48-38+ UUGXJSBPSRROMU-WJNLUYJISA-N Solid Membrane logp 9.73 ALOGPS logs -6.56 ALOGPS solubility 2.18e-04 g/l ALOGPS logp 15.5 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]cyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 795.2265 ChemAxon mono_mass 794.621311112 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)CCC=C(C)C)=C(C)C1=O ChemAxon formula C54H82O4 ChemAxon inchi InChI=1S/C54H82O4/c1-40(2)22-14-23-41(3)24-15-25-42(4)26-16-27-43(5)28-17-29-44(6)30-18-31-45(7)32-19-33-46(8)34-20-35-47(9)36-21-37-48(10)38-39-50-49(11)51(55)53(57-12)54(58-13)52(50)56/h22,24,26,28,30,32,34,36,38H,14-21,23,25,27,29,31,33,35,37,39H2,1-13H3/b41-24+,42-26+,43-28+,44-30+,45-32+,46-34+,47-36+,48-38+ ChemAxon inchikey UUGXJSBPSRROMU-WJNLUYJISA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 262.8 ChemAxon polarizability 103.03 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 71728 Specdb::NmrOneD 255148 Specdb::NmrOneD 255149 Specdb::NmrOneD 255150 Specdb::NmrOneD 255151 Specdb::NmrOneD 255152 Specdb::NmrOneD 255153 Specdb::NmrOneD 255154 Specdb::NmrOneD 255155 Specdb::NmrOneD 255156 Specdb::NmrOneD 255157 Specdb::NmrOneD 255158 Specdb::NmrOneD 255159 Specdb::NmrOneD 255160 Specdb::NmrOneD 255161 Specdb::NmrOneD 255162 Specdb::NmrOneD 255163 Specdb::NmrOneD 255164 Specdb::NmrOneD 255165 Specdb::NmrOneD 255166 Specdb::NmrOneD 255167 Specdb::MsMs 38627 Specdb::MsMs 38628 Specdb::MsMs 38629 Specdb::MsMs 41075 Specdb::MsMs 41076 Specdb::MsMs 41077 Specdb::MsMs 2327697 Specdb::MsMs 2327698 Specdb::MsMs 2327699 Specdb::MsMs 2634509 Specdb::MsMs 2634510 Specdb::MsMs 2634511 HMDB06707 5280473 4444118 C01967 18160 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 Molyneux S, Lever M, Florkowski C, George P: Plasma total coenzyme Q9 (CoQ9) in the New Zealand population: reference interval and biological variation. Clin Chem. 2007 Apr;53(4):802-3. 17405953 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.xml