2.0 2012-07-30 14:54:42 -0600 2015-06-03 17:20:45 -0600 ECMDB21154 M2MDB001563 2-Demethylmenaquinol 8 2-demethylmenaquinol 8 belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure) 2-Demethylmenaquinol-8 DMKH2-8 C50H72O2 705.1055 704.553231548 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]naphthalene-1,4-diol 2-demethylmenaquinol-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)=C1)=C(\C)CCC=C(C)C InChI=1S/C50H72O2/c1-38(2)19-12-20-39(3)21-13-22-40(4)23-14-24-41(5)25-15-26-42(6)27-16-28-43(7)29-17-30-44(8)31-18-32-45(9)35-36-46-37-49(51)47-33-10-11-34-48(47)50(46)52/h10-11,19,21,23,25,27,29,31,33-35,37,51-52H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b39-21+,40-23+,41-25+,42-27+,43-29+,44-31+,45-35+ FGYPGICSXJEKCG-AENDIINCSA-N Membrane logp 10.00 ALOGPS logs -6.48 ALOGPS solubility 2.33e-04 g/l ALOGPS logp 15.7 ChemAxon pka_strongest_acidic 9.16 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]naphthalene-1,4-diol ChemAxon average_mass 705.1055 ChemAxon mono_mass 704.553231548 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)=C1)=C(\C)CCC=C(C)C ChemAxon formula C50H72O2 ChemAxon inchi InChI=1S/C50H72O2/c1-38(2)19-12-20-39(3)21-13-22-40(4)23-14-24-41(5)25-15-26-42(6)27-16-28-43(7)29-17-30-44(8)31-18-32-45(9)35-36-46-37-49(51)47-33-10-11-34-48(47)50(46)52/h10-11,19,21,23,25,27,29,31,33-35,37,51-52H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b39-21+,40-23+,41-25+,42-27+,43-29+,44-31+,45-35+ ChemAxon inchikey FGYPGICSXJEKCG-AENDIINCSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 237.33 ChemAxon polarizability 91.6 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 menaquinol-8 biosynthesis MENAQUINONESYN-PWY demethylmenaquinol-8 biosynthesis I PWY-5852 Specdb::CMs 1088811 Specdb::EiMs 3709 Specdb::NmrOneD 302465 Specdb::NmrOneD 302466 Specdb::NmrOneD 302467 Specdb::NmrOneD 302468 Specdb::NmrOneD 302469 Specdb::NmrOneD 302470 Specdb::NmrOneD 302471 Specdb::NmrOneD 302472 Specdb::NmrOneD 302473 Specdb::NmrOneD 302474 Specdb::NmrOneD 302475 Specdb::NmrOneD 302476 Specdb::NmrOneD 302477 Specdb::NmrOneD 302478 Specdb::NmrOneD 302479 Specdb::NmrOneD 302480 Specdb::NmrOneD 302481 Specdb::NmrOneD 302482 Specdb::NmrOneD 302483 Specdb::NmrOneD 302484 Specdb::MsMs 36359 Specdb::MsMs 36360 Specdb::MsMs 36361 Specdb::MsMs 38807 Specdb::MsMs 38808 Specdb::MsMs 38809 45479277 26332425 61873 CPD-12115 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 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 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 Glycolate oxidase subunit glcD P0AEP9 GLCD_ECOLI glcD http://ecmdb.ca/proteins/P0AEP9.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 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 NADH-quinone oxidoreductase subunit F P31979 NUOF_ECOLI nuoF http://ecmdb.ca/proteins/P31979.xml 1,4-dihydroxy-2-naphthoate octaprenyltransferase P32166 MENA_ECOLI menA http://ecmdb.ca/proteins/P32166.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 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 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 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 Glycolate oxidase subunit glcE P52073 GLCE_ECOLI glcE http://ecmdb.ca/proteins/P52073.xml Hydrogenase-2 operon protein hybA P0AAJ8 HYBA_ECOLI hybA http://ecmdb.ca/proteins/P0AAJ8.xml Trimethylamine-N-oxide reductase 1 P33225 TORA_ECOLI torA http://ecmdb.ca/proteins/P33225.xml Probable Ni/Fe-hydrogenase 2 b-type cytochrome subunit P37180 HYBB_ECOLI hybB http://ecmdb.ca/proteins/P37180.xml Cytochrome c-type protein torC P33226 TORC_ECOLI torC http://ecmdb.ca/proteins/P33226.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml 2-Demethylmenaquinone 8 + 2 Hydrogen ion + Hydrogen (gas) > 2-Demethylmenaquinol 8 +2 Hydrogen ion 2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylamine 2-Demethylmenaquinol 8 + Dimethyl sulfoxide > 2-Demethylmenaquinone 8 + Dimethyl sulfide + Water 2-Demethylmenaquinone 8 + Glycerol 3-phosphate > 2-Demethylmenaquinol 8 + Dihydroxyacetone phosphate 2-Demethylmenaquinone 8 + 4 Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD +3 Hydrogen ion 2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid 2-Demethylmenaquinol 8 + Fumaric acid > 2-Demethylmenaquinone 8 + Succinic acid 2-Demethylmenaquinone 8 + Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD 2-Demethylmenaquinone 8 + Hydrogen ion + NADPH > 2-Demethylmenaquinol 8 + NADP 2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8 ADOMET-DMK-METHYLTRANSFER-RXN 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion + Octaprenyl diphosphate > 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate all-<i>trans</i>-octaprenyl diphosphate + 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion > 2-Demethylmenaquinol 8 + Pyrophosphate + Carbon dioxide DMK-RXN 2-Demethylmenaquinol 8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Menaquinol 8 PW_R005240 1,4-dihydroxy-2-naphthoate + Hydrogen ion + Farnesylfarnesylgeranyl-PP + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8 PW_R005235 Octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + Hydrogen ion + Octaprenyl diphosphate + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8 PW_R005237