2.0 2015-09-08 17:50:28 -0600 2015-09-14 16:46:12 -0600 ECMDB24259 M2MDB006376 3-demethylubiquinol-8 3-Demethylubiquinol-8 belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure) 3-demethylubiquinol-8 is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG) C48H74O4 715.116 714.558710863 3-methoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,2,4-triol 3-methoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,2,4-triol [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)=C(OC)C(O)=C1O)=C(\C)CCC=C(C)C InChI=1S/C48H74O4/c1-35(2)19-12-20-36(3)21-13-22-37(4)23-14-24-38(5)25-15-26-39(6)27-16-28-40(7)29-17-30-41(8)31-18-32-42(9)33-34-44-43(10)45(49)48(52-11)47(51)46(44)50/h19,21,23,25,27,29,31,33,49-51H,12-18,20,22,24,26,28,30,32,34H2,1-11H3/b36-21+,37-23+,38-25+,39-27+,40-29+,41-31+,42-33+ HOLCDWJWFMTVHO-WDXILIIOSA-N logp 9.15 ALOGPS logs -6.32 ALOGPS solubility 3.44e-04 g/l ALOGPS logp 14.76 ChemAxon pka_strongest_acidic 9.93 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 3-methoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,2,4-triol ChemAxon average_mass 715.116 ChemAxon mono_mass 714.558710863 ChemAxon smiles [H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)=C(OC)C(O)=C1O)=C(\C)CCC=C(C)C ChemAxon formula C48H74O4 ChemAxon inchi InChI=1S/C48H74O4/c1-35(2)19-12-20-36(3)21-13-22-37(4)23-14-24-38(5)25-15-26-39(6)27-16-28-40(7)29-17-30-41(8)31-18-32-42(9)33-34-44-43(10)45(49)48(52-11)47(51)46(44)50/h19,21,23,25,27,29,31,33,49-51H,12-18,20,22,24,26,28,30,32,34H2,1-11H3/b36-21+,37-23+,38-25+,39-27+,40-29+,41-31+,42-33+ ChemAxon inchikey HOLCDWJWFMTVHO-WDXILIIOSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 234.37 ChemAxon polarizability 91.25 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Secondary Metabolites: Ubiquinol biosynthesis The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW000981 Metabolic Specdb::CMs 1087788 Specdb::NmrOneD 263248 Specdb::NmrOneD 263249 Specdb::NmrOneD 263250 Specdb::NmrOneD 263251 Specdb::NmrOneD 263252 Specdb::NmrOneD 263253 Specdb::NmrOneD 263254 Specdb::NmrOneD 263255 Specdb::NmrOneD 263256 Specdb::NmrOneD 263257 Specdb::NmrOneD 263258 Specdb::NmrOneD 263259 Specdb::NmrOneD 263260 Specdb::NmrOneD 263261 Specdb::NmrOneD 263262 Specdb::NmrOneD 263263 Specdb::NmrOneD 263264 Specdb::NmrOneD 263265 Specdb::NmrOneD 263266 Specdb::NmrOneD 263267 Specdb::MsMs 41558 Specdb::MsMs 41559 Specdb::MsMs 41560 Specdb::MsMs 42266 Specdb::MsMs 42267 Specdb::MsMs 42268 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.xml 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase P75728 UBIF_ECOLI ubiF http://ecmdb.ca/proteins/P75728.xml 3-demethylubiquinol-8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Ubiquinol 8 + Ubiquinol-8 PW_R003723 Oxygen + Reduced acceptor + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol > Water + oxidized electron acceptor + 3-demethylubiquinol-8 PW_R003722