2.0 2012-05-31 14:24:53 -0600 2015-09-17 15:41:52 -0600 ECMDB20051 M2MDB000900 2-Succinylbenzoate 2-succinylbenzoate is a member of the chemical class known as Benzoic Acid and Derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring. 2-Succinylbenzoate is invovled in the biosynthesis of menaquinone. o-Succinylbenzoate synthase (OSBS) from Escherichia coli, a member of the enolase superfamily, catalyzes an exergonic dehydration reaction in the menaquinone biosynthetic pathway in which 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) is converted to 4-(2'-carboxyphenyl)-4-oxobutyrate (o-succinylbenzoate or OSB). The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. (PMID 3902015) The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. coli strains synthesize an intermediate, "X", which is converted to OSB by extracts of menC+ cells. 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. coli. (PMID 1091286) The committed step in menaquinone biosynthesis is the formation of o-succinylbenzoate (OSB). (PMID 3516220) The suggestion is made that the spirodilactone is the product of an aberrant reaction involving a compound that is normally an intermediate in the conversion of 2-succinylbenzoate to 1,4-dihydroxy-2-naphthoate. (PMID 99177) The presence of shikimic acid in the growth medium restores the ability of an aroD mutant to synthesize cmo5U, while O-succinylbenzoate, which is an early intermediate in the synthesis of menaquinone, does not. (PMID 2104604) 2-(3-Carboxypropanoyl)benzoate 2-(3-Carboxypropanoyl)benzoic acid 2-(3-Carboxypropionyl)benzoate 2-(3-Carboxypropionyl)benzoic acid 2-Carboxy-.gamma.-oxo-Benzenebutanoate 2-Carboxy-.gamma.-oxo-Benzenebutanoic acid 2-Carboxy-g-oxo-benzenebutanoate 2-Carboxy-g-oxo-benzenebutanoic acid 2-Carboxy-gamma-oxo-Benzenebutanoate 2-Carboxy-gamma-oxo-Benzenebutanoic acid 2-Carboxy-γ-oxo-benzenebutanoate 2-Carboxy-γ-oxo-benzenebutanoic acid 2-Succinyl-benzoate 2-Succinyl-benzoic acid 2-Succinylbenzoate 2-Succinylbenzoic acid 4-(2'-Carboxyphenyl)-4-oxobutyrate 4-(2'-Carboxyphenyl)-4-oxobutyric acid 4-(2-Carboxyphenyl)-4-oxobutanoate 4-(2-Carboxyphenyl)-4-oxobutanoic acid <i>o</i>-succinyl-benzoate <i>o</i>-succinylbenzoate NChemBio.2007.11-comp4 O-(3-Carboxypropionyl)-Benzoate O-(3-Carboxypropionyl)-Benzoic acid O-Succinyl-benzoate O-Succinyl-benzoic acid O-Succinylbenzoate O-Succinylbenzoic acid OSB OSucBA Succinylbenzoate Succinylbenzoic acid C11H8O5 220.181 220.038270517 2-(3-carboxypropanoyl)benzoic acid O-succinylbenzoate 27415-09-4 [O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)/p-2 YIVWQNVQRXFZJB-UHFFFAOYSA-L Cytosol logp 0.87 ALOGPS logs -2.60 ALOGPS solubility 5.57e-01 g/l ALOGPS logp 1.01 ChemAxon pka_strongest_acidic 3.42 ChemAxon pka_strongest_basic -7.6 ChemAxon iupac 2-(3-carboxypropanoyl)benzoic acid ChemAxon average_mass 220.181 ChemAxon mono_mass 220.038270517 ChemAxon smiles [O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=O ChemAxon formula C11H8O5 ChemAxon inchi InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)/p-2 ChemAxon inchikey YIVWQNVQRXFZJB-UHFFFAOYSA-L ChemAxon polar_surface_area 91.67 ChemAxon refractivity 54.61 ChemAxon polarizability 21.23 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 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 27629 Specdb::MsMs 27630 Specdb::MsMs 27631 Specdb::MsMs 34187 Specdb::MsMs 34188 Specdb::MsMs 34189 Specdb::MsMs 3607960 Specdb::MsMs 3607961 Specdb::MsMs 3607962 Specdb::MsMs 3607963 Specdb::MsMs 3607964 Specdb::MsMs 3607965 955 930 C02730 18325 O-SUCCINYLBENZOATE OSB 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 Marley, M. G., Meganathan, R., Bentley, R. (1986). "Menaquinone (vitamin K2) biosynthesis in Escherichia coli: synthesis of o-succinylbenzoate does not require the decarboxylase activity of the ketoglutarate dehydrogenase complex." Biochemistry 25:1304-1307. 3516220 Emmons, G. T., Campbell, I. M., Bentley, R. (1985). "Vitamin K (menaquinone) biosynthesis in bacteria: purification and probable structure of an intermediate prior to o-succinylbenzoate." Biochem Biophys Res Commun 131:956-960. 3902015 Young, I. G. (1975). "Biosynthesis of bacterial menaquinones. Menaquinone mutants of Escherichia coli." Biochemistry 14:399-406. 1091286 Hutson, K. G., Threlfall, D. R. (1978). "Formation of spirodilactone of 4-(2'-carboxyphenyl)-4,4-dihydroxybutyrate from 2-succinylbenzoate in cell-free extracts of Micrococcus luteus." Biochim Biophys Acta 530:1-8. 99177 Hagervall, T. G., Jonsson, Y. H., Edmonds, C. G., McCloskey, J. A., Bjork, G. R. (1990). "Chorismic acid, a key metabolite in modification of tRNA." J Bacteriol 172:252-259. 2104604 o-succinylbenzoate synthase P29208 MENC_ECOLI menC http://ecmdb.ca/proteins/P29208.xml 2-succinylbenzoate--CoA ligase P37353 MENE_ECOLI menE http://ecmdb.ca/proteins/P37353.xml Adenosine triphosphate + Coenzyme A + 2-Succinylbenzoate <> Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA R04030 O-SUCCINYLBENZOATE-COA-LIG-RXN (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate <> Water + 2-Succinylbenzoate R04031 O-SUCCINYLBENZOATE-COA-SYN-RXN 2-Succinylbenzoate + Water <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate R04031 Adenosine triphosphate + 2-Succinylbenzoate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA R04030 O-SUCCINYLBENZOATE-COA-LIG-RXN (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-Succinylbenzoate + Water R04031 O-SUCCINYLBENZOATE-COA-SYN-RXN Adenosine triphosphate + 2-Succinylbenzoate + CoA > Adenosine monophosphate + Pyrophosphate + 2-Succinylbenzoyl-CoA (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate > 2-succinylbenzoate + Water + 2-Succinylbenzoate PW_R005217 2-succinylbenzoate + Coenzyme A + Adenosine triphosphate + 2-Succinylbenzoate > 2-Succinylbenzoyl-CoA + Pyrophosphate + Adenosine monophosphate PW_R005221