1.02011-09-21 01:45:10 UTC2015-07-21 06:59:32 UTCFDB0288032-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol2-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-6C38H58O4578.8647578.4335103445-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triol5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triolCOC1=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)=C1OInChI=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,10-14,16,18,20,22,24,26H2,1-9H3ZQXNZNKHQXLVCV-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-methoxyphenolsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsPolyprenylphenolsAromatic homomonocyclic compoundsAlkyl aryl ethersAnisolesHydrocarbon derivativesHydroxyquinols and derivativesMeta cresolsMethoxybenzenesMethoxyphenolsOrtho cresolsPhenoxy compoundsPolyolsPolyprenyl quinolsSesterterpenoidsToluenesUbiquinols2-polyprenyl-6-methoxyphenolAlkyl aryl etherAnisoleAromatic homomonocyclic compoundBenzenoidEtherHydrocarbon derivativeHydroxyquinol derivativeM-cresolMethoxybenzeneMethoxyphenolMonocyclic benzene moietyO-cresolOrganic oxygen compoundOrganooxygen compoundPhenolPhenol etherPhenoxy compoundPolyolPolyprenylbenzoquinolPrenylbenzoquinolSesterterpenoidTolueneUbiquinol skeletona small moleculeSolidlogp8.32logs-5.95solubility6.45e-04 g/llogp11.45pka_strongest_acidic9.96pka_strongest_basic-4.8iupac5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triolaverage_mass578.8647mono_mass578.433510344smilesCOC1=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)=C1OformulaC38H58O4inchiInChI=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,10-14,16,18,20,22,24,26H2,1-9H3inchikeyZQXNZNKHQXLVCV-UHFFFAOYSA-Npolar_surface_area69.92refractivity186.76polarizability71.95rotatable_bond_count18acceptor_count4donor_count3physiological_charge0formal_charge0Specdb::MsMs179484Specdb::MsMs179485Specdb::MsMs179486Specdb::MsMs181812Specdb::MsMs181813Specdb::MsMs181814Specdb::NmrOneD311851Specdb::NmrOneD311852Specdb::NmrOneD311853Specdb::NmrOneD311854Specdb::NmrOneD311855Specdb::NmrOneD311856Specdb::NmrOneD311857Specdb::NmrOneD311858Specdb::NmrOneD311859Specdb::NmrOneD311860Specdb::NmrOneD311861Specdb::NmrOneD311862Specdb::NmrOneD311863Specdb::NmrOneD311864Specdb::NmrOneD311865Specdb::NmrOneD311866Specdb::NmrOneD311867Specdb::NmrOneD311868Specdb::NmrOneD311869Specdb::NmrOneD311870Specdb::CMs1085375HMDB12146AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823