2.0 2012-05-31 14:03:45 -0600 2015-10-15 16:14:25 -0600 ECMDB04055 M2MDB000587 2,3-Dihydro-2,3-dihydroxybenzoic acid 2,3-dihydro-2,3-dihydroxybenzoate 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. 2,3-Dihydro-2,3-dihydroxybenzoate 2,3-Dihydroxy-2,3-dihydrobenzoate 2,3-Dihydroxy-2,3-dihydrobenzoic acid Dihydro-dioh-benzoate Dihydro-dioh-benzoic acid C7H8O4 156.136 156.042258744 5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate 5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate OC1C=CC=C(C1O)C(O)=O InChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11) INCSWYKICIYAHB-UHFFFAOYSA-N Cytosol logp -0.29 ALOGPS logs 0.18 ALOGPS solubility 2.61e+02 g/l ALOGPS logp -0.77 ChemAxon pka_strongest_acidic 4.12 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac 5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate ChemAxon average_mass 156.136 ChemAxon mono_mass 156.042258744 ChemAxon smiles OC1C=CC=C(C1O)C(O)=O ChemAxon formula C7H8O4 ChemAxon inchi InChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11) ChemAxon inchikey INCSWYKICIYAHB-UHFFFAOYSA-N ChemAxon polar_surface_area 80.59 ChemAxon refractivity 49.4 ChemAxon polarizability 13.7 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon 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 2,3-dihydroxybenzoate biosynthesis PWY-5901 Specdb::MsMs 29546 Specdb::MsMs 29547 Specdb::MsMs 29548 Specdb::MsMs 36104 Specdb::MsMs 36105 Specdb::MsMs 36106 23615184 19951064 C04171 15941 DIHYDRO-DIOH-BENZOATE 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 Isochorismatase P0ADI4 ENTB_ECOLI entB http://ecmdb.ca/proteins/P0ADI4.xml 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase P15047 ENTA_ECOLI entA http://ecmdb.ca/proteins/P15047.xml (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD + 2,3-Dihydro-2,3-dihydroxybenzoic acid <> 2-Pyrocatechuic acid + Hydrogen ion + NADH R01505 DHBDEHYD-RXN