2.02012-07-30 14:54:42 -06002015-06-03 17:20:45 -0600ECMDB21154M2MDB0015632-Demethylmenaquinol 82-demethylmenaquinol 8 belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)2-Demethylmenaquinol-8DMKH2-8C50H72O2705.1055704.5532315482-[(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-diol2-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)CInChI=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-NMembranelogp10.00logs-6.48solubility2.33e-04 g/llogp15.7pka_strongest_acidic9.16pka_strongest_basic-6iupac2-[(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-diolaverage_mass705.1055mono_mass704.553231548smiles[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)CformulaC50H72O2inchiInChI=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+inchikeyFGYPGICSXJEKCG-AENDIINCSA-Npolar_surface_area40.46refractivity237.33polarizability91.6rotatable_bond_count23acceptor_count2donor_count2physiological_charge0formal_charge0Menaquinol 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.PW001897Metabolicmenaquinol-8 biosynthesisMENAQUINONESYN-PWYdemethylmenaquinol-8 biosynthesis IPWY-5852Specdb::CMs1088811Specdb::EiMs3709Specdb::NmrOneD302465Specdb::NmrOneD302466Specdb::NmrOneD302467Specdb::NmrOneD302468Specdb::NmrOneD302469Specdb::NmrOneD302470Specdb::NmrOneD302471Specdb::NmrOneD302472Specdb::NmrOneD302473Specdb::NmrOneD302474Specdb::NmrOneD302475Specdb::NmrOneD302476Specdb::NmrOneD302477Specdb::NmrOneD302478Specdb::NmrOneD302479Specdb::NmrOneD302480Specdb::NmrOneD302481Specdb::NmrOneD302482Specdb::NmrOneD302483Specdb::NmrOneD302484Specdb::MsMs36359Specdb::MsMs36360Specdb::MsMs36361Specdb::MsMs38807Specdb::MsMs38808Specdb::MsMs38809454792772633242561873CPD-12115Keseler, 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-D590.21097882Fumarate reductase flavoprotein subunitP00363FRDA_ECOLIfrdAhttp://ecmdb.ca/proteins/P00363.xmlNADH dehydrogenaseP00393DHNA_ECOLIndhhttp://ecmdb.ca/proteins/P00393.xmlFumarate reductase subunit CP0A8Q0FRDC_ECOLIfrdChttp://ecmdb.ca/proteins/P0A8Q0.xmlFumarate reductase subunit DP0A8Q3FRDD_ECOLIfrdDhttp://ecmdb.ca/proteins/P0A8Q3.xmlAnaerobic glycerol-3-phosphate dehydrogenase subunit CP0A996GLPC_ECOLIglpChttp://ecmdb.ca/proteins/P0A996.xmlAnaerobic glycerol-3-phosphate dehydrogenase subunit AP0A9C0GLPA_ECOLIglpAhttp://ecmdb.ca/proteins/P0A9C0.xmlFumarate reductase iron-sulfur subunitP0AC47FRDB_ECOLIfrdBhttp://ecmdb.ca/proteins/P0AC47.xmlHydrogenase-1 large chainP0ACD8MBHL_ECOLIhyaBhttp://ecmdb.ca/proteins/P0ACD8.xmlHydrogenase-2 large chainP0ACE0MBHM_ECOLIhybChttp://ecmdb.ca/proteins/P0ACE0.xmlGlycolate oxidase subunit glcDP0AEP9GLCD_ECOLIglcDhttp://ecmdb.ca/proteins/P0AEP9.xmlNADH-quinone oxidoreductase subunit AP0AFC3NUOA_ECOLInuoAhttp://ecmdb.ca/proteins/P0AFC3.xmlNADH-quinone oxidoreductase subunit BP0AFC7NUOB_ECOLInuoBhttp://ecmdb.ca/proteins/P0AFC7.xmlNADH-quinone oxidoreductase subunit EP0AFD1NUOE_ECOLInuoEhttp://ecmdb.ca/proteins/P0AFD1.xmlNADH-quinone oxidoreductase subunit HP0AFD4NUOH_ECOLInuoHhttp://ecmdb.ca/proteins/P0AFD4.xmlNADH-quinone oxidoreductase subunit IP0AFD6NUOI_ECOLInuoIhttp://ecmdb.ca/proteins/P0AFD6.xmlNADH-quinone oxidoreductase subunit JP0AFE0NUOJ_ECOLInuoJhttp://ecmdb.ca/proteins/P0AFE0.xmlNADH-quinone oxidoreductase subunit KP0AFE4NUOK_ECOLInuoKhttp://ecmdb.ca/proteins/P0AFE4.xmlNADH-quinone oxidoreductase subunit MP0AFE8NUOM_ECOLInuoMhttp://ecmdb.ca/proteins/P0AFE8.xmlNADH-quinone oxidoreductase subunit NP0AFF0NUON_ECOLInuoNhttp://ecmdb.ca/proteins/P0AFF0.xmlAnaerobic glycerol-3-phosphate dehydrogenase subunit BP13033GLPB_ECOLIglpBhttp://ecmdb.ca/proteins/P13033.xmlAnaerobic dimethyl sulfoxide reductase chain AP18775DMSA_ECOLIdmsAhttp://ecmdb.ca/proteins/P18775.xmlAnaerobic dimethyl sulfoxide reductase chain BP18776DMSB_ECOLIdmsBhttp://ecmdb.ca/proteins/P18776.xmlNADH-quinone oxidoreductase subunit FP31979NUOF_ECOLInuoFhttp://ecmdb.ca/proteins/P31979.xml1,4-dihydroxy-2-naphthoate octaprenyltransferaseP32166MENA_ECOLImenAhttp://ecmdb.ca/proteins/P32166.xmlNADH-quinone oxidoreductase subunit C/DP33599NUOCD_ECOLInuoChttp://ecmdb.ca/proteins/P33599.xmlNADH-quinone oxidoreductase subunit GP33602NUOG_ECOLInuoGhttp://ecmdb.ca/proteins/P33602.xmlNADH-quinone oxidoreductase subunit LP33607NUOL_ECOLInuoLhttp://ecmdb.ca/proteins/P33607.xmlGlycolate oxidase iron-sulfur subunitP52074GLCF_ECOLIglcFhttp://ecmdb.ca/proteins/P52074.xmlHydrogenase-1 small chainP69739MBHS_ECOLIhyaAhttp://ecmdb.ca/proteins/P69739.xmlHydrogenase-2 small chainP69741MBHT_ECOLIhybOhttp://ecmdb.ca/proteins/P69741.xmlTrimethylamine-N-oxide reductase 2P46923TORZ_ECOLItorZhttp://ecmdb.ca/proteins/P46923.xmlModulator of drug activity BP0AEY5MDAB_ECOLImdaBhttp://ecmdb.ca/proteins/P0AEY5.xmlCytochrome c-type protein torYP52005TORY_ECOLItorYhttp://ecmdb.ca/proteins/P52005.xmlAnaerobic dimethyl sulfoxide reductase chain CP18777DMSC_ECOLIdmsChttp://ecmdb.ca/proteins/P18777.xmlProbable Ni/Fe-hydrogenase 1 B-type cytochrome subunitP0AAM1CYBH_ECOLIhyaChttp://ecmdb.ca/proteins/P0AAM1.xmlGlycolate oxidase subunit glcEP52073GLCE_ECOLIglcEhttp://ecmdb.ca/proteins/P52073.xmlHydrogenase-2 operon protein hybAP0AAJ8HYBA_ECOLIhybAhttp://ecmdb.ca/proteins/P0AAJ8.xmlTrimethylamine-N-oxide reductase 1P33225TORA_ECOLItorAhttp://ecmdb.ca/proteins/P33225.xmlProbable Ni/Fe-hydrogenase 2 b-type cytochrome subunitP37180HYBB_ECOLIhybBhttp://ecmdb.ca/proteins/P37180.xmlCytochrome c-type protein torCP33226TORC_ECOLItorChttp://ecmdb.ca/proteins/P33226.xmlUbiquinone/menaquinone biosynthesis methyltransferase ubiEP0A887UBIE_ECOLIubiEhttp://ecmdb.ca/proteins/P0A887.xml2-Demethylmenaquinone 8 + 2 Hydrogen ion + Hydrogen (gas) > 2-Demethylmenaquinol 8 +2 Hydrogen ion2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylamine2-Demethylmenaquinol 8 + Dimethyl sulfoxide > 2-Demethylmenaquinone 8 + Dimethyl sulfide + Water2-Demethylmenaquinone 8 + Glycerol 3-phosphate > 2-Demethylmenaquinol 8 + Dihydroxyacetone phosphate2-Demethylmenaquinone 8 + 4 Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD +3 Hydrogen ion2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid2-Demethylmenaquinol 8 + Fumaric acid > 2-Demethylmenaquinone 8 + Succinic acid2-Demethylmenaquinone 8 + Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD2-Demethylmenaquinone 8 + Hydrogen ion + NADPH > 2-Demethylmenaquinol 8 + NADP2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8ADOMET-DMK-METHYLTRANSFER-RXN1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion + Octaprenyl diphosphate > 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphateall-<i>trans</i>-octaprenyl diphosphate + 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion > 2-Demethylmenaquinol 8 + Pyrophosphate + Carbon dioxideDMK-RXN2-Demethylmenaquinol 8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Menaquinol 8PW_R0052401,4-dihydroxy-2-naphthoate + Hydrogen ion + Farnesylfarnesylgeranyl-PP + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8PW_R005235Octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + Hydrogen ion + Octaprenyl diphosphate + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8PW_R005237