2.0 2012-10-22 13:35:01 -0600 2015-06-03 17:26:44 -0600 ECMDB23436 M2MDB003826 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate of 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase that catalyses the following reaction: 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + a reduced electron acceptor + oxygen => 3-demethylubiquinol-8 + an oxidized electron acceptor + H2O C46H70O3 671.0462 670.532496106 5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol 5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol COC1=C(O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C\C=C(/C)CC=C(C)C)=C(C)C(O)=C1 InChI=1S/C46H70O3/c1-34(2)27-28-41(9)30-29-39(7)25-15-23-37(5)21-13-19-35(3)17-12-18-36(4)20-14-22-38(6)24-16-26-40(8)31-32-43-42(10)44(47)33-45(49-11)46(43)48/h17,20-21,24-25,27,30-31,33,47-48H,12-16,18-19,22-23,26,28-29,32H2,1-11H3/b35-17+,36-20+,37-21+,38-24+,39-25+,40-31+,41-30+ CRUUXCIHJFUTIZ-WZVGXJGASA-N Membrane logp 9.24 ALOGPS logs -6.38 ALOGPS solubility 2.78e-04 g/l ALOGPS logp 14.18 ChemAxon pka_strongest_acidic 9.98 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol ChemAxon average_mass 671.0462 ChemAxon mono_mass 670.532496106 ChemAxon smiles COC1=C(O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C\C=C(/C)CC=C(C)C)=C(C)C(O)=C1 ChemAxon formula C46H70O3 ChemAxon inchi InChI=1S/C46H70O3/c1-34(2)27-28-41(9)30-29-39(7)25-15-23-37(5)21-13-19-35(3)17-12-18-36(4)20-14-22-38(6)24-16-26-40(8)31-32-43-42(10)44(47)33-45(49-11)46(43)48/h17,20-21,24-25,27,30-31,33,47-48H,12-16,18-19,22-23,26,28-29,32H2,1-11H3/b35-17+,36-20+,37-21+,38-24+,39-25+,40-31+,41-30+ ChemAxon inchikey CRUUXCIHJFUTIZ-WZVGXJGASA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 223.18 ChemAxon polarizability 85.91 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 3 ChemAxon donor_count 2 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 1085870 Specdb::EiMs 3178 Specdb::NmrOneD 283389 Specdb::NmrOneD 283390 Specdb::NmrOneD 283391 Specdb::NmrOneD 283392 Specdb::NmrOneD 283393 Specdb::NmrOneD 283394 Specdb::NmrOneD 283395 Specdb::NmrOneD 283396 Specdb::NmrOneD 283397 Specdb::NmrOneD 283398 Specdb::NmrOneD 283399 Specdb::NmrOneD 283400 Specdb::NmrOneD 283401 Specdb::NmrOneD 283402 Specdb::NmrOneD 283403 Specdb::NmrOneD 283404 Specdb::NmrOneD 283405 Specdb::NmrOneD 283406 Specdb::NmrOneD 283407 Specdb::NmrOneD 283408 Specdb::MsMs 36533 Specdb::MsMs 36534 Specdb::MsMs 36535 Specdb::MsMs 38981 Specdb::MsMs 38982 Specdb::MsMs 38983 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase P75728 UBIF_ECOLI ubiF http://ecmdb.ca/proteins/P75728.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Hydrogen ion + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol PW_R003721 Oxygen + Reduced acceptor + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol > Water + oxidized electron acceptor + 3-demethylubiquinol-8 PW_R003722