2.0 2012-07-30 14:54:41 -0600 2015-06-03 17:20:43 -0600 ECMDB21138 M2MDB001547 2,3-Dihydroxybenzoylserine 2,3-dihydroxybenzoylserine is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 2,3-dihydroxybenzoylserine is invovled in Enterobactin degradation. It is a product of the enzyme 2,3-dihydroxybenzoate-serine ligase (EC 6.3.2.14) is an enzyme that catalyzes the chemical reaction ATP + 2,3-dihydroxybenzoate + L-serine ightleftharpoons products of ATP breakdown + N-(2,3-dihydroxybenzoyl)-L-serine. (PMID 4966114). 2,3-Dihydroxy-N-benzoyl-L-serine 2,3-dihydroxybenzoylserine 2,3DHBSer 2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoate 2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoic acid N-(2,3-Dihydroxybenzoyl)-L-serine C10H11NO6 241.1974 241.058637089 (2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid 2,3,-dihydroxybenzoylserine 127658-43-9 [H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=O InChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1 VDTYHTVHFIIEIL-LURJTMIESA-N Cytosol logp 0.33 ALOGPS logs -1.62 ALOGPS solubility 5.76e+00 g/l ALOGPS logp 0.09 ChemAxon pka_strongest_acidic 2.98 ChemAxon pka_strongest_basic -2 ChemAxon iupac (2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid ChemAxon average_mass 241.1974 ChemAxon mono_mass 241.058637089 ChemAxon smiles [H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=O ChemAxon formula C10H11NO6 ChemAxon inchi InChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1 ChemAxon inchikey VDTYHTVHFIIEIL-LURJTMIESA-N ChemAxon polar_surface_area 127.09 ChemAxon refractivity 56.12 ChemAxon polarizability 22.06 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 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 Specdb::CMs 1084538 Specdb::MsMs 25481 Specdb::MsMs 25482 Specdb::MsMs 25483 Specdb::MsMs 32039 Specdb::MsMs 32040 Specdb::MsMs 32041 25244759 133509 C04204 17455 N-23-DIHYDROXYBENZOYL-L-SERINE DBS 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 Enterochelin esterase P13039 FES_ECOLI fes http://ecmdb.ca/proteins/P13039.xml Enterochelin + 3 Water >3 2,3-Dihydroxybenzoylserine +3 Hydrogen ion RXN0-1661 Ferric enterobactin + 3 Water >3 2,3-Dihydroxybenzoylserine + Fe3+ +3 Hydrogen ion Enterochelin + Water > Hydrogen ion + 2,3-Dihydroxybenzoylserine RXN0-1661 (2,3-dihydroxybenzoylserine)₃ + Water 2,3-Dihydroxybenzoylserine RXN0-6944