2.02012-08-09 09:25:18 -06002015-06-03 17:21:43 -0600ECMDB21529M2MDB001924Farnesylfarnesylgeranyl-PPFarnesylfarnesylgeranyl-PP is a member of the chemical class known as Tetraterpenes. These are terpene molecules containing 8 consecutively linked isoprene units. It is an intermediate in ubiquinone biosysnthesis in the reaction farnesylfarnesylgeranyl-PP + p-hydroxybenzoate = 3-octaprenyl-4-hydroxybenzoate + pyrophosphate All-trans-octaprenyl diphosphateall-trans-Octaprenyl diphosphoric acidC40H65O7P2719.8874719.420552458{[(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 phosphonato]oxy}phosphonate[(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 phosphonato]oxyphosphonate[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])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)CInChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/p-3/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+IKKLDISSULFFQO-DJMILUHSSA-KMembranelogp7.92logs-6.25solubility4.37e-04 g/llogp11.92pka_strongest_acidic1.77iupac{[(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 phosphonato]oxy}phosphonateaverage_mass719.8874mono_mass719.420552458smiles[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])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)CformulaC40H65O7P2inchiInChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/p-3/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+inchikeyIKKLDISSULFFQO-DJMILUHSSA-Kpolar_surface_area121.78refractivity212.38polarizability84.1rotatable_bond_count26acceptor_count5donor_count0physiological_charge-2formal_charge-3Menaquinol biosythesisMenaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate.
The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol.PW001897MetabolicSpecdb::MsMs29225Specdb::MsMs29226Specdb::MsMs29227Specdb::MsMs35783Specdb::MsMs35784Specdb::MsMs3578526330884van 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 370:17-25.177651951,4-dihydroxy-2-naphthoate octaprenyltransferaseP32166MENA_ECOLImenAhttp://ecmdb.ca/proteins/P32166.xml4-hydroxybenzoate octaprenyltransferaseP0AGK1UBIA_ECOLIubiAhttp://ecmdb.ca/proteins/P0AGK1.xml1,4-dihydroxy-2-naphthoate + Hydrogen ion + Farnesylfarnesylgeranyl-PP + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8PW_R005235