1.0 2011-09-21 01:38:25 UTC 2015-07-21 06:59:23 UTC FDB028352 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2) is an intermediate in coenzyme Q biosynthesis. It is produced by gut microbes. In microbes, the starting compound, 4-hydroxybenzoate, undergoes a prenylation, a decarboxylation and three hydroxylations alternating with three methylation reactions, resulting in the formation of coenzyme Q. In the final step, DMQH2 is converted from 2-octaprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) with the help of Methyltransferase. Coenzyme Q (ubiquinone or Q)1 is a redox active lipid containing a long polyprenyl tail attached to a fully substituted benzoquinone ring. The number (n) of isoprene units in the polyprenyl tail (Qn) is distinct in different organisms; humans produce Q10, Caenorhabditis elegans Q9, Escherichia coli Q8, and Saccharomyces cerevisiae Q6. [HMDB] 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol 5-Demethoxyubiquinol DMQH2 C38H60O3 564.8812 564.454245786 3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol 3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol COC1=CC(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1O InChI=1S/C38H60O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27,36,38-40H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+ VFOCBGJJNKIBIS-NSUIJKAQSA-N belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Sesterterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesterterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Sesterterpenoid Solid logp 7.59 ALOGPS logs -6.01 ALOGPS solubility 5.58e-04 g/l ALOGPS logp 9.24 ChemAxon pka_strongest_acidic 13.24 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac 3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol ChemAxon average_mass 564.8812 ChemAxon mono_mass 564.454245786 ChemAxon smiles COC1=CC(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1O ChemAxon formula C38H60O3 ChemAxon inchi InChI=1S/C38H60O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27,36,38-40H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+ ChemAxon inchikey VFOCBGJJNKIBIS-NSUIJKAQSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 185.98 ChemAxon polarizability 72.38 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 178704 Specdb::MsMs 178705 Specdb::MsMs 178706 Specdb::MsMs 181023 Specdb::MsMs 181024 Specdb::MsMs 181025 Specdb::MsMs 2790818 Specdb::MsMs 2790819 Specdb::MsMs 2790820 Specdb::MsMs 2914376 Specdb::MsMs 2914377 Specdb::MsMs 2914378 Specdb::CMs 19447 Specdb::CMs 39750 Specdb::CMs 282105 Specdb::CMs 359009 Specdb::CMs 359010 Specdb::CMs 359011 Specdb::CMs 359012 Specdb::CMs 359013 HMDB11661 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