2.02012-10-22 13:35:01 -06002015-06-03 17:26:44 -0600ECMDB23437M2MDB0038272-methoxy-6-(all-trans-octaprenyl)phenol2-methoxy-6-(all-trans-octaprenyl)phenol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate for the 2-octaprenyl-6-methoxyphenol hydroxylase that catalyses the following reaction: 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH + oxygen + H+ => 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + NADP+ + H2O2-Octaprenyl-6-methoxyphenol6-methoxy-2-octaprenylphenolC40H58O2570.8873570.44368112-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenol2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenolCOC1=CC=CC(C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)CC=C(C)C)=C1OInChI=1S/C40H58O2/c1-30(2)14-15-31(3)16-17-32(4)18-19-33(5)20-21-34(6)22-23-35(7)24-25-36(8)26-27-37(9)28-29-38-12-11-13-39(42-10)40(38)41/h11-14,16,18,20,22,24,26,28,41H,15,17,19,21,23,25,27,29H2,1-10H3/b31-16+,32-18+,33-20+,34-22+,35-24+,36-26+,37-28+CSWHQXJYVAFCED-KBSPPPJMSA-NMembranelogp8.92logs-6.24solubility3.30e-04 g/llogp11.75pka_strongest_acidic9.79pka_strongest_basic-4.9iupac2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenolaverage_mass570.8873mono_mass570.4436811smilesCOC1=CC=CC(C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)CC=C(C)C)=C1OformulaC40H58O2inchiInChI=1S/C40H58O2/c1-30(2)14-15-31(3)16-17-32(4)18-19-33(5)20-21-34(6)22-23-35(7)24-25-36(8)26-27-37(9)28-29-38-12-11-13-39(42-10)40(38)41/h11-14,16,18,20,22,24,26,28,41H,15,17,19,21,23,25,27,29H2,1-10H3/b31-16+,32-18+,33-20+,34-22+,35-24+,36-26+,37-28+inchikeyCSWHQXJYVAFCED-KBSPPPJMSA-Npolar_surface_area29.46refractivity193.16polarizability72.6rotatable_bond_count17acceptor_count2donor_count1physiological_charge0formal_charge0Secondary Metabolites: Ubiquinol biosynthesisThe 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.
PW000981MetabolicSecondary Metabolites: Ubiquinol biosynthesis 2The 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.PW002036MetabolicSpecdb::CMs1089691Specdb::EiMs3361Specdb::MsMs23555Specdb::MsMs23556Specdb::MsMs23557Specdb::MsMs24227Specdb::MsMs24228Specdb::MsMs24229Specdb::MsMs30353Specdb::MsMs30354Specdb::MsMs3035512353-demethylubiquinone-9 3-methyltransferaseP17993UBIG_ECOLIubiGhttp://ecmdb.ca/proteins/P17993.xml2-octaprenyl-6-methoxyphenol hydroxylaseP25534UBIH_ECOLIubiHhttp://ecmdb.ca/proteins/P25534.xml2-Octaprenyl-6-hydroxyphenol + S-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenolPW_R003719Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinolPW_R003720