2.0 2012-07-30 14:54:43 -0600 2015-06-03 17:20:46 -0600 ECMDB21158 M2MDB001567 2-Octaprenyl-6-methoxy-1,4-benzoquinol 2-octaprenyl-6-methoxy-1,4-benzoquinol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure) 2-Methoxy-6-octaprenyl-2-methoxy-1,4-benzoquinol 2-Methoxy-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-1,4-diol 2-Octaprenyl-6-methoxy-1,4-benzoquinol 6-Methoxy-2-octaprenylquinol C47H72O3 685.0728 684.54814617 2-methoxy-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-1,4-diol 6-methoxy-2-octaprenylquinol [H]OC1=C([H])C(=C(O[H])C(OC([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] InChI=1S/C47H72O3/c1-36(2)18-11-19-37(3)20-12-21-38(4)22-13-23-39(5)24-14-25-40(6)26-15-27-41(7)28-16-29-42(8)30-17-31-43(9)32-33-44-34-45(48)35-46(50-10)47(44)49/h18,20,22,24,26,28,30,32,34-35,48-49H,11-17,19,21,23,25,27,29,31,33H2,1-10H3/b37-20+,38-22+,39-24+,40-26+,41-28+,42-30+,43-32+ CZFRMASEEPTBAQ-MYCGWMCTSA-N Membrane logp 9.57 ALOGPS logs -6.42 ALOGPS solubility 2.61e-04 g/l ALOGPS logp 14.56 ChemAxon pka_strongest_acidic 9.73 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxy-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-1,4-diol ChemAxon average_mass 685.0728 ChemAxon mono_mass 684.54814617 ChemAxon smiles [H]OC1=C([H])C(=C(O[H])C(OC([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] ChemAxon formula C47H72O3 ChemAxon inchi InChI=1S/C47H72O3/c1-36(2)18-11-19-37(3)20-12-21-38(4)22-13-23-39(5)24-14-25-40(6)26-15-27-41(7)28-16-29-42(8)30-17-31-43(9)32-33-44-34-45(48)35-46(50-10)47(44)49/h18,20,22,24,26,28,30,32,34-35,48-49H,11-17,19,21,23,25,27,29,31,33H2,1-10H3/b37-20+,38-22+,39-24+,40-26+,41-28+,42-30+,43-32+ ChemAxon inchikey CZFRMASEEPTBAQ-MYCGWMCTSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 227.34 ChemAxon polarizability 89.19 ChemAxon rotatable_bond_count 24 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 Secondary Metabolites: Ubiquinol biosynthesis 2 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. PW002036 Metabolic ubiquinol-8 biosynthesis (prokaryotic) PWY-6708 Specdb::CMs 1088667 Specdb::NmrOneD 291155 Specdb::NmrOneD 291156 Specdb::NmrOneD 291157 Specdb::NmrOneD 291158 Specdb::NmrOneD 291159 Specdb::NmrOneD 291160 Specdb::NmrOneD 291161 Specdb::NmrOneD 291162 Specdb::NmrOneD 291163 Specdb::NmrOneD 291164 Specdb::NmrOneD 291165 Specdb::NmrOneD 291166 Specdb::NmrOneD 291167 Specdb::NmrOneD 291168 Specdb::NmrOneD 291169 Specdb::NmrOneD 291170 Specdb::NmrOneD 291171 Specdb::NmrOneD 291172 Specdb::NmrOneD 291173 Specdb::NmrOneD 291174 Specdb::MsMs 1218781 Specdb::MsMs 1218782 Specdb::MsMs 1218783 Specdb::MsMs 1334494 Specdb::MsMs 1334495 Specdb::MsMs 1334496 49852329 26331999 60655 OCTAPRENYL-METHOXY-BENZOQUINONE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 2-octaprenyl-6-methoxyphenol hydroxylase P25534 UBIH_ECOLI ubiH http://ecmdb.ca/proteins/P25534.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml 2-Octaprenyl-6-methoxyphenol + Oxygen > 2-Octaprenyl-6-methoxy-1,4-benzoquinol 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion 2-OCTAPRENYL-METHOXY-BENZOQ-METH-RXN 2-Octaprenyl-6-methoxyphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP 2-OCTAPRENYL-6-METHOXYPHENOL-HYDROX-RXN Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinol PW_R003720 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 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion PW_R005949