2.0 2012-05-31 14:30:47 -0600 2015-09-17 15:41:51 -0600 ECMDB20162 M2MDB001009 Isochorismate Isochorismate is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. In Escherichia coli, isochorismate is a common precursor for the biosynthesis of the siderophore enterobactin and menaquinone (vitamin K2). Isochorismate is formed by the shikimate pathway from chorismate by the enzyme isochorismate synthase encoded by the entC gene. (PMID 8655506) Iso-chorismate Iso-chorismic acid Isochorismic acid C10H8O6 224.169 224.033185137 (5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid isochorismic acid 22642-82-6 [H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/p-2/t7-,8-/m0/s1 NTGWPRCCOQCMGE-YUMQZZPRSA-L Cytosol logp 0.69 ALOGPS logs -1.34 ALOGPS solubility 1.04e+01 g/l ALOGPS logp -0.13 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid ChemAxon average_mass 224.169 ChemAxon mono_mass 224.033185137 ChemAxon smiles [H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O ChemAxon formula C10H8O6 ChemAxon inchi InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/p-2/t7-,8-/m0/s1 ChemAxon inchikey NTGWPRCCOQCMGE-YUMQZZPRSA-L ChemAxon polar_surface_area 104.06 ChemAxon refractivity 54.31 ChemAxon polarizability 20.37 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Biosynthesis of siderophore group nonribosomal peptides 2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. The biosynthesis of 2,3-dihydroxybenzoate starts from chorismate being synthesized into isochorismate through isochorismate synthase entC. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.This compound then interacts with L-serine and ATP through enterobactin synthase protein complex resulting in the production of enterobactin. Enterobactin is exported into the periplasmic space through the enterobactin exporter entS. The compound is the export to the environment through the outer membrane protein TolC. In the environment enterobactin reacts with iron to produce Ferric enterobactin. This compound is imported into the periplasmic space through a ferric enterobactin outermembrane transport complex. The compound then enters the cytoplasm through a ferric enterobactin ABC transporter.Once inside the cytoplasm, ferric enterobactin spontaneously releases the iron ion from the enterobactin. PW000760 ec01053 Metabolic Metabolic pathways eco01100 2,3-dihydroxybenzoate biosynthesis 2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds. The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes EntC, EntB, and EntA. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase. PW000751 Metabolic 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 Enterobactin Biosynthesis Enterobactin is a catecholate siderophore produced almost exclusively by enterobacteria, although it has been reported in some Streptomyces species. It is a cyclic compound made of three units of 2,3-dihydroxybenzoylserine joined in a cyclic structure by lactone linkages (only the δ-cis isomer of the ferric chelate is biologically active). Not only the cyclic molecule, but also the biosynthetic precursor 2,3-dihydroxy-N-benzoylserine and its linear dimer and trimer condensation products are able to transport iron into enterobacteria. Enterobactin is synthesized under iron-deficient conditions and excreted into the environment where it binds Fe(III) with high affinity and specificity. The ferrisiderophore complexes are taken up into the cell by specific transport components. Enterobactin synthesis is divided into two parts: 1) the conversion of chorismate to 2,3-dihydroxybenzoate 2) the synthesis of enterobactin from 2,3-dihydroxybenzoate and L-serine. (EcoCyc) PW002048 Metabolic 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837 2,3-dihydroxybenzoate biosynthesis PWY-5901 Specdb::MsMs 25688 Specdb::MsMs 25689 Specdb::MsMs 25690 Specdb::MsMs 32246 Specdb::MsMs 32247 Specdb::MsMs 32248 Specdb::MsMs 3608713 Specdb::MsMs 3608714 Specdb::MsMs 3608715 Specdb::MsMs 3608716 Specdb::MsMs 3608717 Specdb::MsMs 3608718 189062 787 C00885 29780 ISOCHORISMATE ISC 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 Kwon, O., Hudspeth, M. E., Meganathan, R. (1996). "Anaerobic biosynthesis of enterobactin Escherichia coli: regulation of entC gene expression and evidence against its involvement in menaquinone (vitamin K2) biosynthesis." J Bacteriol 178:3252-3259. 8655506 Isochorismatase P0ADI4 ENTB_ECOLI entB http://ecmdb.ca/proteins/P0ADI4.xml Isochorismate synthase entC P0AEJ2 ENTC_ECOLI entC http://ecmdb.ca/proteins/P0AEJ2.xml 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P17109 MEND_ECOLI menD http://ecmdb.ca/proteins/P17109.xml Menaquinone-specific isochorismate synthase P38051 MENF_ECOLI menF http://ecmdb.ca/proteins/P38051.xml Chorismate <> Isochorismate R01717 ISOCHORSYN-RXN Water + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acid R03037 ISOCHORMAT-RXN alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide 2.5.1.64-RXN Isochorismate + Water > 2,3-dihydroxy-2,3-dihydrobenzoate + Pyruvic acid Chorismate > Isochorismate Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide Chorismate > isochorismate + Isochorismate PW_R002452 Water + isochorismate + Isochorismate > Pyruvic acid + 2,3-dihydroxy-2,3-dihydrobenzoate PW_R002453 isochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate PW_R005214