2.0 2012-05-31 14:03:42 -0600 2015-09-17 16:24:11 -0600 ECMDB04054 M2MDB000586 1,4-Dihydroxy-2-naphthoic acid 1,4-dihydroxy-2-naphthoate is a member of the chemical class known as Naphthalenecarboxylic Acids and Derivatives. These are compounds containing a napthalene moiety with a ring carbon which bears a carboxylic acid group. 1,4-dihydroxy-2-naphthoate is invovled in ubiquinone and other terpenoid-quinone biosynthesis, and the biosynthesis of secondary metabolites. It has been postulated that 1,4-dihydroxy-2-naphthoic acid is the naphthalenic intermediate in the biosynthesis of menaquinone (vitamin K2) in Escherichia coli to which the octaprenyl side chain is attached to from demethylmenaquinone. (PMID 949474) It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. (PMID 1091286) 1,4-Dihydroxy-2-naphthalenecarboxylate 1,4-Dihydroxy-2-naphthalenecarboxylic acid 1,4-Dihydroxy-2-naphthoate 1,4-Dihydroxy-2-naphthoic acid 1,4DHNaphA DHNA C11H8O4 204.1788 204.042258744 (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-dioxidonaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanecarboximidate (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-dioxidonaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanecarboximidate 31519-22-9 OC(=O)C1=C(O)C2=CC=CC=C2C(O)=C1 InChI=1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15) VOJUXHHACRXLTD-UHFFFAOYSA-N Cytosol Membrane logp 0.94 ALOGPS logs -2.14 ALOGPS solubility 7.42e+00 g/l ALOGPS melting_point 170.33 logp 1.17 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic -4.3 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-dioxidonaphthalene-2-carbonylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanecarboximidate ChemAxon average_mass 204.1788 ChemAxon mono_mass 204.042258744 ChemAxon smiles OC(=O)C1=C(O)C2=CC=CC=C2C(O)=C1 ChemAxon formula C11H8O4 ChemAxon inchi InChI=1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15) ChemAxon inchikey VOJUXHHACRXLTD-UHFFFAOYSA-N ChemAxon polar_surface_area 422.39 ChemAxon refractivity 256.54 ChemAxon polarizability 86.95 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 21 ChemAxon donor_count 7 ChemAxon physiological_charge -4 ChemAxon formal_charge -4 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 demethylmenaquinol-8 biosynthesis I PWY-5852 Specdb::NmrOneD 276798 Specdb::NmrOneD 276799 Specdb::NmrOneD 276800 Specdb::NmrOneD 276801 Specdb::NmrOneD 276802 Specdb::NmrOneD 276803 Specdb::NmrOneD 276804 Specdb::NmrOneD 276805 Specdb::NmrOneD 276806 Specdb::NmrOneD 276807 Specdb::NmrOneD 276808 Specdb::NmrOneD 276809 Specdb::NmrOneD 276810 Specdb::NmrOneD 276811 Specdb::NmrOneD 276812 Specdb::NmrOneD 276813 Specdb::NmrOneD 276814 Specdb::NmrOneD 276815 Specdb::NmrOneD 276816 Specdb::NmrOneD 276817 671 651 C03657 18094 DIHYDROXYNAPHTHOATE DNA 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Young, I. G. (1975). "Biosynthesis of bacterial menaquinones. Menaquinone mutants of Escherichia coli." Biochemistry 14:399-406. 1091286 Shineberg, B., Young, I. G. (1976). "Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli." Biochemistry 15:2754-2758. 949474 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 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion + Octaprenyl diphosphate > 2-Demethylmenaquinol 8 + Carbon dioxide + Pyrophosphate 1,4-Dihydroxy-2-naphthoic acid + Octaprenyl diphosphate <> 2-Demethylmenaquinone 8 + Pyrophosphate + Carbon dioxide R05617 1,4-Dihydroxy-2-naphthoic acid + Phytyl diphosphate <> 2-Phytyl-1,4-naphthoquinone + Carbon dioxide + Pyrophosphate R06858 all-<i>trans</i>-octaprenyl diphosphate + 1,4-Dihydroxy-2-naphthoic acid + Hydrogen ion > 2-Demethylmenaquinol 8 + Pyrophosphate + Carbon dioxide DMK-RXN An all-trans-polyprenyl diphosphate + 1,4-Dihydroxy-2-naphthoic acid > a demethylmenaquinol + Pyrophosphate + Carbon dioxide Geranyl-PP + 1,4-Dihydroxy-2-naphthoic acid <> Demethylmenaquinol + Pyrophosphate + Carbon dioxide R10757