1.0 2011-09-21 01:45:10 UTC 2015-07-21 06:59:32 UTC FDB028803 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is an ubiquinone derivative that is an intermediate in ubiquinone-6 biosynthesis. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes ubiquinone is found mostly within the inner mitochondrial membrane, where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate , while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway , which feeds isoprene units into the Polyprenyl Biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain vary in different species. For example, Saccharomyces cerevisiae subsp (S288c) has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. The ubiquinones are often named according to the number of carbons in the side chain or the number of isoprenoid subunits. The ubiquinone biosynthesis pathway has been elucidated primarily by the use of mutant strains that accumulate pathway intermediates. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is a substrate for hexaprenyldihydroxybenzoate methyltransferase, mitochondrial precursor (COQ3) and can be generated from 2-hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol. Then it can be converted to ubiquinol-6.(BioCyc) [HMDB] Demethyl-ubiquinol-6 C38H58O4 578.8647 578.433510344 5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triol 5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triol COC1=C(O)C(O)=C(C)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C1O InChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3 ZQXNZNKHQXLVCV-UHFFFAOYSA-N belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group. 2-polyprenyl-6-methoxyphenols Organic compounds Lipids and lipid-like molecules Prenol lipids Polyprenylphenols Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Hydrocarbon derivatives Hydroxyquinols and derivatives Meta cresols Methoxybenzenes Methoxyphenols Ortho cresols Phenoxy compounds Polyols Polyprenyl quinols Sesterterpenoids Toluenes Ubiquinols 2-polyprenyl-6-methoxyphenol Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Ether Hydrocarbon derivative Hydroxyquinol derivative M-cresol Methoxybenzene Methoxyphenol Monocyclic benzene moiety O-cresol Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Polyol Polyprenylbenzoquinol Prenylbenzoquinol Sesterterpenoid Toluene Ubiquinol skeleton a small molecule Solid logp 8.32 ALOGPS logs -5.95 ALOGPS solubility 6.45e-04 g/l ALOGPS logp 11.45 ChemAxon pka_strongest_acidic 9.96 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triol ChemAxon average_mass 578.8647 ChemAxon mono_mass 578.433510344 ChemAxon smiles COC1=C(O)C(O)=C(C)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C1O ChemAxon formula C38H58O4 ChemAxon inchi InChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3 ChemAxon inchikey ZQXNZNKHQXLVCV-UHFFFAOYSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 186.76 ChemAxon polarizability 71.95 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 179484 Specdb::MsMs 179485 Specdb::MsMs 179486 Specdb::MsMs 181812 Specdb::MsMs 181813 Specdb::MsMs 181814 Specdb::CMs 1085375 Specdb::NmrOneD 311851 Specdb::NmrOneD 311852 Specdb::NmrOneD 311853 Specdb::NmrOneD 311854 Specdb::NmrOneD 311855 Specdb::NmrOneD 311856 Specdb::NmrOneD 311857 Specdb::NmrOneD 311858 Specdb::NmrOneD 311859 Specdb::NmrOneD 311860 Specdb::NmrOneD 311861 Specdb::NmrOneD 311862 Specdb::NmrOneD 311863 Specdb::NmrOneD 311864 Specdb::NmrOneD 311865 Specdb::NmrOneD 311866 Specdb::NmrOneD 311867 Specdb::NmrOneD 311868 Specdb::NmrOneD 311869 Specdb::NmrOneD 311870 HMDB12146 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 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