2.02015-09-08 17:48:47 -06002015-09-08 17:48:47 -0600ECMDB24056M2MDB006173Ubiquinol 8C49H78O4731.1412730.5900109842,3-dimethoxy-5-methyl-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-diolubiquinol-8COC1=C(OC)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)CC\C=C(/C)CCC=C(C)C)=C(C)C1OInChI=1S/C49H78O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,46-47,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+FLVUMORHBJZINO-SGHXUWJISA-Nlogp9.35logs-6.43solubility2.73e-04 g/llogp14.91pka_strongest_acidic10.27pka_strongest_basic-4.7iupac2,3-dimethoxy-5-methyl-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-diolaverage_mass731.1412mono_mass730.590010984smilesCOC1=C(OC)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)CC\C=C(/C)CCC=C(C)C)=C(C)C1OformulaC49H78O4inchiInChI=1S/C49H78O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,46-47,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+inchikeyFLVUMORHBJZINO-SGHXUWJISA-Npolar_surface_area58.92refractivity238.85polarizability94.28rotatable_bond_count25acceptor_count4donor_count2physiological_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.
PW000981MetabolicTCA cycle (ubiquinol-8)The TCA pathway is a catabolic pathway of aerobic respiration. It generates energy and reducing power. It is the first step in generating precursors for biosynthesis. When acetate is the carbon source, citrate synthase is rate-limiting for the TCA cycle. Respiration is an ATP-generating process in which compounds act as electron donors through a chain of electron transfer to electron acceptors. Aerobic respiration uses oxygen as the final acceptor. Anaerobic respiration uses several organic compounds as acceptors such as fumarate, nitrate and hydrogen. During the chain of electron transfer, protons (H+) are transported outside the cytoplasmic membrane, generating a proton motive force. Upon passage of protons back into the cytoplasm, the PMF energy is captured as ATP, catalyzed by a multisubunit ATPase.
The cycle can start from Acetyl-CoA interacting with Oxalacetic acid and water through a citrate synthase monomer resulting in a hydrogen ion, CoA and a Citric Acid. The latter compound is dehydrated by a Citrate hydro-lyase resulting in the release of water and a cis-Aconitic acid. This compound is then hydrated through a Citrate hydro-lyase resulting in a D-threo-Isocitric acid. This compound is decarboxylated by an NADP dependent Citrate dehydrogenase, resulting in a release of carbon dioxide and NADPH and Oxoglutaric acid. The oxoglutaric acid interacts with a Coenzyme A through a NAD driven 2-oxoglutarate dehydrogenase resulting in a release of carbon dioxide, an NADH and succinyl-CoA. The succinyl-CoA interacts with a phosphate and an ADP through a 2-oxoglutarate dehydrogenase resulting in a CoA, an ATP and Succinic Acid. Succinic acid interacts with a ubiquinone, in this case a ubiquinone 1 through a succinate:quinone oxidoreductase resulting in an ubiquinol, in this case a ubiquinol-1 and a fumaric acid.
The fumaric acid interacts with water through a fumarase hydratase resulting in a L-Malic acid.This compound can either interact with quinone through a malate:quinone oxidoreductase resulting in a release of hydroquinone and oxalacetic acid, or it can react with an NAD through a malate dehydrogenase resulting in a hydrogen ion, NADH and Oxalacetic acid.PW001008MetabolicSpecdb::CMs765630Specdb::CMs765631Specdb::CMs765632Specdb::CMs765633Specdb::CMs765634Specdb::MsMs1256260Specdb::MsMs1256261Specdb::MsMs1256262Specdb::MsMs1371439Specdb::MsMs1371440Specdb::MsMs1371441Specdb::MsMs2346947Specdb::MsMs2346948Specdb::MsMs2346949Specdb::MsMs2591710Specdb::MsMs2591711Specdb::MsMs2591712