1.0 2010-04-08 22:13:39 UTC 2019-11-26 03:16:02 UTC FDB018340 Ubiquinone 4 Isolated from various yeasts Ubiquinone Q4 is a Coenzyme Q analogue that have been identified in brain. Coenzyme Q is the only type of Quinones naturally found in animals (other quinones such as vitamin K is provided by foods). Coenzyme Q is a fat-soluble and amphipathic compound that is the integral component of the electron transport chain in mitochondria. It is ubiquitous in nature and is found in subcellular organelles, serum lipoproteins, blood plasma, urine, and feces. Ubiquinones are amphipathic because of the benzoquinone ring (hydrophilic) and the polyisoprenoid side chain moiety (lipophilic). The primary role of coenzyme Q is to transfer electrons between redox components of the electron transport chain, to create a proton gradient across the inner mitochondrial membrane and drive ATP formation. Additional functions of coenzyme Q are to influence membrane fluidity; and, most important, to act as a lipid antioxidant protecting membrane phospholipids against peroxidation. Coenzyme Q is the only endogenously occurring lipid-soluble antioxidant that occurs ubiquitously and can be synthesized in all organisms. Based on the isoprenoid moiety, the presence of various coenzyme Q homologues in prokaryotes and eurkaryotes has been confirmed, and these homologues are classified as Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, and Q12. The numbers, Qn, refer to the amount of isoprenoid units attached at the 6- position on the benzoquinone ring of the coenzyme Q moiety. (PMID: 12064350); to recycle the radical forms of vitamin C and E 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-2,5-cyclohexadiene-1,4-dione 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-P-benzoquinone 2,3-Dimethoxy-5-methyl-6-(geranylgeranyl)-1,4-benzoquinone 2,3-Dimethoxy-5-methyl-6-[(2e,6e,10e)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2,5-cyclohexadiene-1,4-dione Coenzyme Q4 CoQ4 Ubiquinone 4 Ubiquinone q4 C29H42O4 454.6414 454.308309832 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione ubiquinone 4 4370-62-1 COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O InChI=1S/C29H42O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+ XGCJRRDNIMSYNC-INVBOZNNSA-N belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). Ubiquinones Organic compounds Lipids and lipid-like molecules Prenol lipids Quinone and hydroquinone lipids Aliphatic homomonocyclic compounds Diterpenoids Hydrocarbon derivatives Organic oxides P-benzoquinones Vinylogous esters Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Diterpenoid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound P-benzoquinone Quinone Ubiquinone skeleton Vinylogous ester Ubiquinones Solid logp 6.53 ALOGPS logs -5.71 ALOGPS solubility 8.88e-04 g/l ALOGPS logp 7.2 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 454.6414 ChemAxon mono_mass 454.308309832 ChemAxon smiles COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ChemAxon formula C29H42O4 ChemAxon inchi InChI=1S/C29H42O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+ ChemAxon inchikey XGCJRRDNIMSYNC-INVBOZNNSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 143.79 ChemAxon polarizability 55.21 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2265 Specdb::CMs 2268 Specdb::CMs 21549 Specdb::CMs 31541 Specdb::CMs 31542 Specdb::CMs 134715 Specdb::CMs 142449 Specdb::MsMs 28289 Specdb::MsMs 28290 Specdb::MsMs 28291 Specdb::MsMs 34847 Specdb::MsMs 34848 Specdb::MsMs 34849 Specdb::MsMs 2772383 Specdb::MsMs 2772384 Specdb::MsMs 2772385 Specdb::MsMs 2909085 Specdb::MsMs 2909086 Specdb::MsMs 2909087 HMDB06710 #<Reference:0x000055ce323b5528> Alcoholic beverages Unknown generic Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Breakfast cereal Type 2 specific Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Cereals and cereal products Unknown generic Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823