2.0 2012-07-30 14:55:06 -0600 2015-06-03 17:20:59 -0600 ECMDB21245 M2MDB001653 Menaquinol 8 Menaquinol 8 is a polyprenylhydroquinone having a an octaprenyl moiety at position 2 and a methyl group at position 3. It is a substrate for Dimethyl sulfoxide reductase (dmsA). This enzyme catalyzes the reduction of dimethyl sulfoxide (DMSO) to dimethyl sulfide (DMS) using the following reaction: Dimethylsulfide + menaquinone + H2O = dimethylsulfoxide + menaquinol. DMSO reductase serves as the terminal reductase under anaerobic conditions, with DMSO being the terminal electron acceptor. Terminal reductase during anaerobic growth on various sulfoxides and N-oxide compounds. This enzyme allows E.coli to grow anaerobically on DMSO as respiratory oxidant. Menaquinol 8 is generated by Ubiquinone/menaquinone biosynthesis methyltransferase (ubiE). This enzyme is required for the conversion of demethylmenaquinone (DMKH2) to menaquinone (MKH2) and has the following catalytic activity: A demethylmenaquinone + S-adenosyl-L-methionine = a menaquinol + S-adenosyl-L-homocysteine. MKH2-8 Reduced menaquinone-8 C51H74O2 719.1321 718.568881612 2-methyl-3-[(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]naphthalene-1,4-diol menaquinol-8 [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])CC1=C(O)C2=CC=CC=C2C(O)=C1C)=C(\C)CCC=C(C)C InChI=1S/C51H74O2/c1-38(2)20-13-21-39(3)22-14-23-40(4)24-15-25-41(5)26-16-27-42(6)28-17-29-43(7)30-18-31-44(8)32-19-33-45(9)36-37-47-46(10)50(52)48-34-11-12-35-49(48)51(47)53/h11-12,20,22,24,26,28,30,32,34-36,52-53H,13-19,21,23,25,27,29,31,33,37H2,1-10H3/b39-22+,40-24+,41-26+,42-28+,43-30+,44-32+,45-36+ OIEZRVBFVPGODT-WQWYCSGDSA-N Membrane logp 9.92 ALOGPS logs -6.49 ALOGPS solubility 2.33e-04 g/l ALOGPS logp 16.22 ChemAxon pka_strongest_acidic 9.38 ChemAxon pka_strongest_basic -6 ChemAxon iupac 2-methyl-3-[(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]naphthalene-1,4-diol ChemAxon average_mass 719.1321 ChemAxon mono_mass 718.568881612 ChemAxon smiles [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])CC1=C(O)C2=CC=CC=C2C(O)=C1C)=C(\C)CCC=C(C)C ChemAxon formula C51H74O2 ChemAxon inchi InChI=1S/C51H74O2/c1-38(2)20-13-21-39(3)22-14-23-40(4)24-15-25-41(5)26-16-27-42(6)28-17-29-43(7)30-18-31-44(8)32-19-33-45(9)36-37-47-46(10)50(52)48-34-11-12-35-49(48)51(47)53/h11-12,20,22,24,26,28,30,32,34-36,52-53H,13-19,21,23,25,27,29,31,33,37H2,1-10H3/b39-22+,40-24+,41-26+,42-28+,43-30+,44-32+,45-36+ ChemAxon inchikey OIEZRVBFVPGODT-WQWYCSGDSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 242.37 ChemAxon polarizability 93.44 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Menaquinol biosythesis Menaquinol 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. PW001897 Metabolic N-oxide electron transfer The pathway can start in various spots. First step in this case starts with NADH interacting with a menaquinone oxidoreductase resulting in the release of a NADH and a hydrogen Ion, at the same time in the inner membrane a menaquinone interacts with 2 electrons and 2 hydrogen ions thus releasing a menaquinol. This allows for 4 hydrogen ions to be transferred from the cytosol to the periplasmic space. The menaquinol then interacts with a trimethylamine N-oxide reductase resulting in the release of 2 hydrogen ion and 2 electrons. At the same time trimethylamine N-oxide and 3 hydrogen ions interact with the enzyme trimethylamine N-oxide reductase resulting in the release of a trimethylamine and a water molecule, this reaction happening in the periplasmic space. The second set of reactions starts with a hydrogen interacting with a menaquinone oxidoreductase resulting in the release of two electrons being released into the inner membrane which then react with with 2 hydrogen ion and a menaquinone to produce a menaquinol. This menaquinol then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before. The third set of reactions starts with with formate interacting with a formate dehydrogenase-O resulting in a release of carbon dioxide and a hydrogen ion, this releases 2 electrons that interact with a menaquinone and two hydrogen ions. This releases a menaquinol which then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before PW001889 Metabolic dimethyl sulfoxide electron transfer The pathway can start in various spots. First step in this case starts with NADH interacting with a menaquinone oxidoreductase resulting in the release of a NADH and a hydrogen Ion, at the same time in the inner membrane a menaquinone interacts with 2 electrons and 2 hydrogen ions thus releasing a menaquinol. This allows for 4 hydrogen ions to be transferred from the cytosol to the periplasmic space. The menaquinol then interacts with a dimethyl sulfoxide reductase resulting in the release of 2 hydrogen ion and 2 electrons. At the same time dimethyl sulfoxide and 2 hydrogen ions interact with the enzyme resulting in the release of a dimethyl sulfide and a water molecule, this reaction happening in the periplasmic space. The second set of reactions starts with a hydrogen interacting with a menaquinone oxidoreductase resulting in the release of two electrons being released into the inner membrane which then react with with 2 hydrogen ion and a menaquinone to produce a menaquinol. This menaquinol then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before. The third set of reactions starts with with formate interacting with a formate dehydrogenase-O resulting in a release of carbon dioxide and a hydrogen ion, this releases 2 electrons that interact with a menaquinone and two hydrogen ions. This releases a menaquinol which then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before PW001892 Metabolic glycerol metabolism Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through a glycerophosphodiester reacting with water through a glycerophosphoryl diester phosphodiesterase or it can also be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000914 Metabolic glycerol metabolism II Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphocholine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000915 Metabolic glycerol metabolism III (sn-glycero-3-phosphoethanolamine) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphethanolamine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000916 Metabolic glycerol metabolism IV (glycerophosphoglycerol) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoglycerol reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000917 Metabolic glycerol metabolism V (glycerophosphoserine) Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoserine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000918 Metabolic menaquinol-8 biosynthesis MENAQUINONESYN-PWY Specdb::CMs 1088110 Specdb::NmrOneD 300385 Specdb::NmrOneD 300386 Specdb::NmrOneD 300387 Specdb::NmrOneD 300388 Specdb::NmrOneD 300389 Specdb::NmrOneD 300390 Specdb::NmrOneD 300391 Specdb::NmrOneD 300392 Specdb::NmrOneD 300393 Specdb::NmrOneD 300394 Specdb::NmrOneD 300395 Specdb::NmrOneD 300396 Specdb::NmrOneD 300397 Specdb::NmrOneD 300398 Specdb::NmrOneD 300399 Specdb::NmrOneD 300400 Specdb::NmrOneD 300401 Specdb::NmrOneD 300402 Specdb::NmrOneD 300403 Specdb::NmrOneD 300404 Specdb::MsMs 36602 Specdb::MsMs 36603 Specdb::MsMs 36604 Specdb::MsMs 39050 Specdb::MsMs 39051 Specdb::MsMs 39052 45479636 26332321 61684 REDUCED-MENAQUINONE 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 Fumarate reductase flavoprotein subunit P00363 FRDA_ECOLI frdA http://ecmdb.ca/proteins/P00363.xml NADH dehydrogenase P00393 DHNA_ECOLI ndh http://ecmdb.ca/proteins/P00393.xml Respiratory nitrate reductase 1 alpha chain P09152 NARG_ECOLI narG http://ecmdb.ca/proteins/P09152.xml Dihydroorotate dehydrogenase P0A7E1 PYRD_ECOLI pyrD http://ecmdb.ca/proteins/P0A7E1.xml Fumarate reductase subunit C P0A8Q0 FRDC_ECOLI frdC http://ecmdb.ca/proteins/P0A8Q0.xml Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI frdD http://ecmdb.ca/proteins/P0A8Q3.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit C P0A996 GLPC_ECOLI glpC http://ecmdb.ca/proteins/P0A996.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit A P0A9C0 GLPA_ECOLI glpA http://ecmdb.ca/proteins/P0A9C0.xml Probable anaerobic dimethyl sulfoxide reductase chain ynfG P0AAJ1 YNFG_ECOLI ynfG http://ecmdb.ca/proteins/P0AAJ1.xml Formate dehydrogenase, nitrate-inducible, iron-sulfur subunit P0AAJ3 FDNH_ECOLI fdnH http://ecmdb.ca/proteins/P0AAJ3.xml Formate dehydrogenase-O iron-sulfur subunit P0AAJ5 FDOH_ECOLI fdoH http://ecmdb.ca/proteins/P0AAJ5.xml Cytochrome c-552 P0ABK9 NRFA_ECOLI nrfA http://ecmdb.ca/proteins/P0ABK9.xml Fumarate reductase iron-sulfur subunit P0AC47 FRDB_ECOLI frdB http://ecmdb.ca/proteins/P0AC47.xml Hydrogenase-1 large chain P0ACD8 MBHL_ECOLI hyaB http://ecmdb.ca/proteins/P0ACD8.xml Hydrogenase-2 large chain P0ACE0 MBHM_ECOLI hybC http://ecmdb.ca/proteins/P0ACE0.xml Probable quinol monooxygenase ygiN P0ADU2 YGIN_ECOLI ygiN http://ecmdb.ca/proteins/P0ADU2.xml Formate dehydrogenase, nitrate-inducible, cytochrome b556(fdn) subunit P0AEK7 FDNI_ECOLI fdnI http://ecmdb.ca/proteins/P0AEK7.xml Formate dehydrogenase, cytochrome b556(fdo) subunit P0AEL0 FDOI_ECOLI fdoI http://ecmdb.ca/proteins/P0AEL0.xml Glycolate oxidase subunit glcD P0AEP9 GLCD_ECOLI glcD http://ecmdb.ca/proteins/P0AEP9.xml Respiratory nitrate reductase 2 gamma chain P0AF32 NARV_ECOLI narV http://ecmdb.ca/proteins/P0AF32.xml NADH-quinone oxidoreductase subunit A P0AFC3 NUOA_ECOLI nuoA http://ecmdb.ca/proteins/P0AFC3.xml NADH-quinone oxidoreductase subunit B P0AFC7 NUOB_ECOLI nuoB http://ecmdb.ca/proteins/P0AFC7.xml NADH-quinone oxidoreductase subunit E P0AFD1 NUOE_ECOLI nuoE http://ecmdb.ca/proteins/P0AFD1.xml NADH-quinone oxidoreductase subunit H P0AFD4 NUOH_ECOLI nuoH http://ecmdb.ca/proteins/P0AFD4.xml NADH-quinone oxidoreductase subunit I P0AFD6 NUOI_ECOLI nuoI http://ecmdb.ca/proteins/P0AFD6.xml NADH-quinone oxidoreductase subunit J P0AFE0 NUOJ_ECOLI nuoJ http://ecmdb.ca/proteins/P0AFE0.xml NADH-quinone oxidoreductase subunit K P0AFE4 NUOK_ECOLI nuoK http://ecmdb.ca/proteins/P0AFE4.xml NADH-quinone oxidoreductase subunit M P0AFE8 NUOM_ECOLI nuoM http://ecmdb.ca/proteins/P0AFE8.xml NADH-quinone oxidoreductase subunit N P0AFF0 NUON_ECOLI nuoN http://ecmdb.ca/proteins/P0AFF0.xml L-aspartate oxidase P10902 NADB_ECOLI nadB http://ecmdb.ca/proteins/P10902.xml Respiratory nitrate reductase 1 beta chain P11349 NARH_ECOLI narH http://ecmdb.ca/proteins/P11349.xml Respiratory nitrate reductase 1 gamma chain P11350 NARI_ECOLI narI http://ecmdb.ca/proteins/P11350.xml Anaerobic glycerol-3-phosphate dehydrogenase subunit B P13033 GLPB_ECOLI glpB http://ecmdb.ca/proteins/P13033.xml Anaerobic dimethyl sulfoxide reductase chain A P18775 DMSA_ECOLI dmsA http://ecmdb.ca/proteins/P18775.xml Anaerobic dimethyl sulfoxide reductase chain B P18776 DMSB_ECOLI dmsB http://ecmdb.ca/proteins/P18776.xml Probable nitrate reductase molybdenum cofactor assembly chaperone NarW P19317 NARW_ECOLI narW http://ecmdb.ca/proteins/P19317.xml Respiratory nitrate reductase 2 beta chain P19318 NARY_ECOLI narY http://ecmdb.ca/proteins/P19318.xml Respiratory nitrate reductase 2 alpha chain P19319 NARZ_ECOLI narZ http://ecmdb.ca/proteins/P19319.xml Formate dehydrogenase, nitrate-inducible, major subunit P24183 FDNG_ECOLI fdnG http://ecmdb.ca/proteins/P24183.xml NADH-quinone oxidoreductase subunit F P31979 NUOF_ECOLI nuoF http://ecmdb.ca/proteins/P31979.xml Formate dehydrogenase-O major subunit P32176 FDOG_ECOLI fdoG http://ecmdb.ca/proteins/P32176.xml L-lactate dehydrogenase [cytochrome] P33232 LLDD_ECOLI lldD http://ecmdb.ca/proteins/P33232.xml NADH-quinone oxidoreductase subunit C/D P33599 NUOCD_ECOLI nuoC http://ecmdb.ca/proteins/P33599.xml NADH-quinone oxidoreductase subunit G P33602 NUOG_ECOLI nuoG http://ecmdb.ca/proteins/P33602.xml NADH-quinone oxidoreductase subunit L P33607 NUOL_ECOLI nuoL http://ecmdb.ca/proteins/P33607.xml Periplasmic nitrate reductase P33937 NAPA_ECOLI napA http://ecmdb.ca/proteins/P33937.xml Malate:quinone oxidoreductase P33940 MQO_ECOLI mqo http://ecmdb.ca/proteins/P33940.xml Glycolate oxidase iron-sulfur subunit P52074 GLCF_ECOLI glcF http://ecmdb.ca/proteins/P52074.xml Hydrogenase-1 small chain P69739 MBHS_ECOLI hyaA http://ecmdb.ca/proteins/P69739.xml Hydrogenase-2 small chain P69741 MBHT_ECOLI hybO http://ecmdb.ca/proteins/P69741.xml Putative dimethyl sulfoxide reductase chain ynfE P77374 YNFE_ECOLI ynfE http://ecmdb.ca/proteins/P77374.xml Probable dimethyl sulfoxide reductase chain ynfF P77783 YNFF_ECOLI ynfF http://ecmdb.ca/proteins/P77783.xml Trimethylamine-N-oxide reductase 2 P46923 TORZ_ECOLI torZ http://ecmdb.ca/proteins/P46923.xml Modulator of drug activity B P0AEY5 MDAB_ECOLI mdaB http://ecmdb.ca/proteins/P0AEY5.xml Uncharacterized protein ykgE P77252 YKGE_ECOLI ykgE http://ecmdb.ca/proteins/P77252.xml Cytochrome c-type protein torY P52005 TORY_ECOLI torY http://ecmdb.ca/proteins/P52005.xml Anaerobic dimethyl sulfoxide reductase chain C P18777 DMSC_ECOLI dmsC http://ecmdb.ca/proteins/P18777.xml Probable Ni/Fe-hydrogenase 1 B-type cytochrome subunit P0AAM1 CYBH_ECOLI hyaC http://ecmdb.ca/proteins/P0AAM1.xml Uncharacterized protein ykgG P77433 YKGG_ECOLI ykgG http://ecmdb.ca/proteins/P77433.xml Glycolate oxidase subunit glcE P52073 GLCE_ECOLI glcE http://ecmdb.ca/proteins/P52073.xml Thiol:disulfide interchange protein dsbA P0AEG4 DSBA_ECOLI dsbA http://ecmdb.ca/proteins/P0AEG4.xml Hydrogenase-2 operon protein hybA P0AAJ8 HYBA_ECOLI hybA http://ecmdb.ca/proteins/P0AAJ8.xml Uncharacterized electron transport protein ykgF P77536 YKGF_ECOLI ykgF http://ecmdb.ca/proteins/P77536.xml Cytochrome bd-II oxidase subunit 2 P26458 APPB_ECOLI appB http://ecmdb.ca/proteins/P26458.xml Trimethylamine-N-oxide reductase 1 P33225 TORA_ECOLI torA http://ecmdb.ca/proteins/P33225.xml Protein nrfD P32709 NRFD_ECOLI nrfD http://ecmdb.ca/proteins/P32709.xml Probable Ni/Fe-hydrogenase 2 b-type cytochrome subunit P37180 HYBB_ECOLI hybB http://ecmdb.ca/proteins/P37180.xml Cytochrome bd-II oxidase subunit 1 P26459 APPC_ECOLI appC http://ecmdb.ca/proteins/P26459.xml Cytochrome c-type protein torC P33226 TORC_ECOLI torC http://ecmdb.ca/proteins/P33226.xml Protein nrfC P0AAK7 NRFC_ECOLI nrfC http://ecmdb.ca/proteins/P0AAK7.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml Cytochrome c-type protein nrfB P0ABL1 NRFB_ECOLI nrfB http://ecmdb.ca/proteins/P0ABL1.xml Diheme cytochrome c napB P0ABL3 NAPB_ECOLI napB http://ecmdb.ca/proteins/P0ABL3.xml Anaerobic dimethyl sulfoxide reductase chain ynfH P76173 YNFH_ECOLI ynfH http://ecmdb.ca/proteins/P76173.xml Disulfide bond formation protein B P0A6M2 DSBB_ECOLI dsbB http://ecmdb.ca/proteins/P0A6M2.xml Cytochrome c-type protein napC P0ABL5 NAPC_ECOLI napC http://ecmdb.ca/proteins/P0ABL5.xml Nitrate reductase molybdenum cofactor assembly chaperone NarJ P0AF26 NARJ_ECOLI narJ http://ecmdb.ca/proteins/P0AF26.xml Hydrogen ion + Menaquinol 8 + Trimethylamine N-Oxide > Water + Menaquinone 8 + Trimethylamine 2 Hydrogen ion + Hydrogen (gas) + Menaquinone 8 > Menaquinol 8 +2 Hydrogen ion 2 Hydrogen ion + Menaquinol 8 + Nitrate > Water + Menaquinone 8 + Nitrite +2 Hydrogen ion 2 Hydrogen ion + Menaquinone 8 + Formic acid > Menaquinol 8 + Carbon dioxide + Hydrogen ion Dimethyl sulfoxide + Menaquinol 8 > Dimethyl sulfide + Water + Menaquinone 8 Menaquinol 8 + Nitrate > Menaquinone 8 + Water + Nitrite 2 Hydrogen ion + Menaquinol 8 + Oxygen > Water + Menaquinone 8 +2 Hydrogen ion Menaquinol 8 + Selenocystathionine > Water + Menaquinone 8 + Selenite Glycerol 3-phosphate + Menaquinone 8 > Dihydroxyacetone phosphate + Menaquinol 8 4 Hydrogen ion + Menaquinone 8 + NADH > Menaquinol 8 + NAD +3 Hydrogen ion Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 8 L-Lactic acid + Menaquinone 8 > Menaquinol 8 + Pyruvic acid Menaquinone 8 + periplasmic protein disulfide isomerase I (reduced) > Menaquinol 8 + periplasmic protein disulfide isomerase I (oxidized) 3 Menaquinol 8 + 2 Hydrogen ion + Nitrite >3 Menaquinone 8 +2 Water + Ammonium Fumaric acid + Menaquinol 8 > Menaquinone 8 + Succinic acid 4,5-Dihydroorotic acid + Menaquinone 8 > Menaquinol 8 + Orotic acid Hydrogen ion + Menaquinone 8 + NADH > Menaquinol 8 + NAD L-Malic acid + Menaquinone 8 > Menaquinol 8 + Oxalacetic acid L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8 Hydrogen ion + Menaquinone 8 + NADPH > Menaquinol 8 + NADP Menaquinol 8 + 2 Oxygen >2 Hydrogen ion + Menaquinone 8 +2 Superoxide anion 2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8 ADOMET-DMK-METHYLTRANSFER-RXN Glycerol 3-phosphate + menaquinone-8 > Menaquinol 8 + Dihydroxyacetone phosphate PW_R003440 2-Demethylmenaquinol 8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Menaquinol 8 PW_R005240 NADH + 4 Hydrogen ion + 2 Hydrogen ion + menaquinone-8 NAD + Hydrogen ion + Menaquinol 8 + Electron +4 Hydrogen ion PW_RCT000172 Trimethylamine N-Oxide + 3 Hydrogen ion + Menaquinol 8 + 2 Electron > Trimethylamine + Water +2 Hydrogen ion + menaquinone-8 PW_RCT000173 Hydrogen ion + Electron + 2 Hydrogen ion + menaquinone-8 > Menaquinol 8 + Hydrogen ion PW_RCT000174 Formic acid + menaquinone-8 + Electron + Hydrogen ion > Carbon dioxide + Hydrogen ion + Menaquinol 8 PW_RCT000175 Menaquinol 8 + Dimethyl sulfoxide + 2 Hydrogen ion + 2 Electron > menaquinone-8 + Dimethyl sulfide + Water +2 Hydrogen ion PW_RCT000176