2.0 2012-05-31 14:05:43 -0600 2015-06-03 15:54:45 -0600 ECMDB04120 M2MDB000622 2-Octaprenylphenol 2-octaprenylphenol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)2-octaprenylphenol is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)Octaprenylphenol is the CoQ biosynthetic intermediate found to accumulate in E. Coli. (PMID 10960098) 2OctPhe C46H70O 639.0474 638.542666862 2-[(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]phenol 2-octaprenylphenol 42187-47-3 CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC=CC=C1O InChI=1S/C46H70O/c1-37(2)19-12-20-38(3)21-13-22-39(4)23-14-24-40(5)25-15-26-41(6)27-16-28-42(7)29-17-30-43(8)31-18-32-44(9)35-36-45-33-10-11-34-46(45)47/h10-11,19,21,23,25,27,29,31,33-35,47H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-35+ VUNQJPPPTJIREN-CMAXTTDKSA-N Membrane logp 10.01 ALOGPS logs -6.45 ALOGPS solubility 2.26e-04 g/l ALOGPS logp 15.02 ChemAxon pka_strongest_acidic 9.33 ChemAxon pka_strongest_basic -6 ChemAxon iupac 2-[(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]phenol ChemAxon average_mass 639.0474 ChemAxon mono_mass 638.542666862 ChemAxon smiles CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC=CC=C1O ChemAxon formula C46H70O ChemAxon inchi InChI=1S/C46H70O/c1-37(2)19-12-20-38(3)21-13-22-39(4)23-14-24-40(5)25-15-26-41(6)27-16-28-42(7)29-17-30-43(8)31-18-32-44(9)35-36-45-33-10-11-34-46(45)47/h10-11,19,21,23,25,27,29,31,33-35,47H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-35+ ChemAxon inchikey VUNQJPPPTJIREN-CMAXTTDKSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 218.9 ChemAxon polarizability 85.73 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 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 1088910 Specdb::NmrOneD 322712 Specdb::NmrOneD 322713 Specdb::NmrOneD 322714 Specdb::NmrOneD 322715 Specdb::NmrOneD 322716 Specdb::NmrOneD 322717 Specdb::NmrOneD 322718 Specdb::NmrOneD 322719 Specdb::NmrOneD 322720 Specdb::NmrOneD 322721 Specdb::NmrOneD 322722 Specdb::NmrOneD 322723 Specdb::NmrOneD 322724 Specdb::NmrOneD 322725 Specdb::NmrOneD 322726 Specdb::NmrOneD 322727 Specdb::NmrOneD 322728 Specdb::NmrOneD 322729 Specdb::NmrOneD 322730 Specdb::NmrOneD 322731 Specdb::MsMs 23501 Specdb::MsMs 23502 Specdb::MsMs 23503 Specdb::MsMs 30299 Specdb::MsMs 30300 Specdb::MsMs 30301 Specdb::MsMs 3607948 Specdb::MsMs 3607949 Specdb::MsMs 3607950 Specdb::MsMs 3607951 Specdb::MsMs 3607952 Specdb::MsMs 3607953 5280832 4444381 C05810 40407 2-OCTAPRENYLPHENOL 8PP 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 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 3-octaprenyl-4-hydroxybenzoate carboxy-lyase P0AAB4 UBID_ECOLI ubiD http://ecmdb.ca/proteins/P0AAB4.xml Probable ubiquinone biosynthesis protein ubiB P0A6A0 UBIB_ECOLI ubiB http://ecmdb.ca/proteins/P0A6A0.xml 3-octaprenyl-4-hydroxybenzoate carboxy-lyase P0AG03 UBIX_ECOLI ubiX http://ecmdb.ca/proteins/P0AG03.xml 3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion > 2-Octaprenylphenol + Carbon dioxide R04986 3-OCTAPRENYL-4-OHBENZOATE-DECARBOX-RXN 2-Octaprenylphenol + Oxygen > 2-Octaprenyl-6-hydroxyphenol 3-Octaprenyl-4-hydroxybenzoate <> 2-Octaprenylphenol + Carbon dioxide R04986 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <> 2-Octaprenyl-6-hydroxyphenol + NADP + Water R04987 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-hydroxyphenol + Water + NADP R04987 2-OCTAPRENYLPHENOL-HYDROX-RXN 2-Octaprenylphenol + Hydrogen ion + NADPH + Oxygen + NADPH > NADP + Water + 2-Octaprenyl-6-hydroxyphenol + 2-Octaprenyl-6-hydroxyphenol PW_R003718 2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water 3 3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion >2 2-Octaprenylphenol + Carbon dioxide 2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water