2.0 2012-05-31 14:23:53 -0600 2015-09-17 15:41:52 -0600 ECMDB20032 M2MDB000881 1,4-Dihydroxy-2-naphthoyl-CoA 1,4-dihydroxy-2-naphthoyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. 1,4-Dihydroxy-2-naphthoyl-CoA is involved menaquinone biosynthetic pathway. 1,4-dihydroxy-2-naphthoate (DHNA) is a branch point metabolite leading to the biosynthesis of menaquinone (vitamin K2 in bacteria) and begins with the conjugation of DHNA with the CoA moiety via 1,4-Dihydroxy-2-naphthoyl coenzyme A (DHNA-CoA) synthase. (PMID 20643650) 1,4-Dihydroxy-2-naphthoate-CoA 1,4-Dihydroxy-2-naphthoic acid-CoA DHNA-CoA C32H38N7O19P3S 949.67 949.117798519 (2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-(1,4-dihydroxynaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-(2-{[2-(1,4-dihydroxynaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O InChI=1S/C32H42N7O19P3S/c1-32(2,26(44)29(45)35-8-7-21(41)34-9-10-62-31(46)18-11-19(40)16-5-3-4-6-17(16)23(18)42)13-55-61(52,53)58-60(50,51)54-12-20-25(57-59(47,48)49)24(43)30(56-20)39-15-38-22-27(33)36-14-37-28(22)39/h3-6,11,14-15,20,24-26,30,40,42-44H,7-10,12-13H2,1-2H3,(H,34,41)(H,35,45)(H,50,51)(H,52,53)(H2,33,36,37)(H2,47,48,49)/p-4/t20-,24-,25-,26+,30-/m1/s1 PYTINLGPKDJURZ-HSJNEKGZSA-J Cytosol logp 0.55 ALOGPS logs -2.23 ALOGPS solubility 5.63e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.79 ChemAxon iupac (2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-(1,4-dihydroxynaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid ChemAxon average_mass 949.67 ChemAxon mono_mass 949.117798519 ChemAxon smiles [H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O ChemAxon formula C32H38N7O19P3S ChemAxon inchi InChI=1S/C32H42N7O19P3S/c1-32(2,26(44)29(45)35-8-7-21(41)34-9-10-62-31(46)18-11-19(40)16-5-3-4-6-17(16)23(18)42)13-55-61(52,53)58-60(50,51)54-12-20-25(57-59(47,48)49)24(43)30(56-20)39-15-38-22-27(33)36-14-37-28(22)39/h3-6,11,14-15,20,24-26,30,40,42-44H,7-10,12-13H2,1-2H3,(H,34,41)(H,35,45)(H,50,51)(H,52,53)(H2,33,36,37)(H2,47,48,49)/p-4/t20-,24-,25-,26+,30-/m1/s1 ChemAxon inchikey PYTINLGPKDJURZ-HSJNEKGZSA-J ChemAxon polar_surface_area 411.07 ChemAxon refractivity 214.33 ChemAxon polarizability 86.05 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 21 ChemAxon donor_count 11 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Metabolic pathways eco01100 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 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837 Specdb::MsMs 24626 Specdb::MsMs 24627 Specdb::MsMs 24628 Specdb::MsMs 31184 Specdb::MsMs 31185 Specdb::MsMs 31186 Specdb::MsMs 3607807 Specdb::MsMs 3607808 Specdb::MsMs 3607809 Specdb::MsMs 3607810 Specdb::MsMs 3607811 Specdb::MsMs 3607812 11954202 10128497 C15547 CPD-9925 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 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Jiang, M., Chen, M., Guo, Z. F., Guo, Z. (2010). "A bicarbonate cofactor modulates 1,4-dihydroxy-2-naphthoyl-coenzyme a synthase in menaquinone biosynthesis of Escherichia coli." J Biol Chem 285:30159-30169. 20643650 Naphthoate synthase P0ABU0 MENB_ECOLI menB http://ecmdb.ca/proteins/P0ABU0.xml 1,4-dihydroxy-2-naphthoate octaprenyltransferase P32166 MENA_ECOLI menA http://ecmdb.ca/proteins/P32166.xml Acyl-CoA thioester hydrolase YbgC P0A8Z3 YBGC_ECOLI ybgC http://ecmdb.ca/proteins/P0A8Z3.xml 1,4-Dihydroxy-2-naphthoyl-CoA + Water > Coenzyme A + 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion RXN-9311 Hydrogen ion + 2-Succinylbenzoyl-CoA > 1,4-Dihydroxy-2-naphthoyl-CoA + Water R07263 NAPHTHOATE-SYN-RXN 2-Succinylbenzoyl-CoA <> 1,4-Dihydroxy-2-naphthoyl-CoA + Water R07263 NAPHTHOATE-SYN-RXN 4-(2-Carboxyphenyl)-4-oxobutanoyl-CoA > 1,4-Dihydroxy-2-naphthoyl-CoA + Water 2-Succinylbenzoyl-CoA + Hydrogen ion > Water + 1,4-dihydroxy-2-naphthoyl-CoA + 1,4-Dihydroxy-2-naphthoyl-CoA PW_R005226 1,4-dihydroxy-2-naphthoyl-CoA + Water + 1,4-Dihydroxy-2-naphthoyl-CoA > Coenzyme A + Hydrogen ion + 1,4-dihydroxy-2-naphthoate PW_R005231 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