2.0 2012-05-31 10:26:32 -0600 2015-09-13 12:56:08 -0600 ECMDB00397 M2MDB000134 2-Pyrocatechuic acid 2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG) 2,3-Dihydroxybenzoate 2,3-Dihydroxybenzoic acid 2-Pyrocatechuate 2-Pyrocatechuic acid 3-Hydroxysalicylate 3-Hydroxysalicylic acid Catechol-3-carboxylate Catechol-3-carboxylic acid Catecholcarboxylate Catecholcarboxylic acid DHBA DOBK O-Pyrocatechuate O-Pyrocatechuic acid Pyrocatechuate Pyrocatechuic acid C7H6O4 154.1201 154.02660868 2,3-dihydroxybenzoic acid 2,3-dihydroxy-benzoic acid 303-38-8 OC(=O)C1=CC=CC(O)=C1O InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) GLDQAMYCGOIJDV-UHFFFAOYSA-N Cytosol logp 1.42 ALOGPS logs -1.35 ALOGPS solubility 6.88e+00 g/l ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 2.56 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 2,3-dihydroxybenzoic acid ChemAxon average_mass 154.1201 ChemAxon mono_mass 154.02660868 ChemAxon smiles OC(=O)C1=CC=CC(O)=C1O ChemAxon formula C7H6O4 ChemAxon inchi InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) ChemAxon inchikey GLDQAMYCGOIJDV-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 37.28 ChemAxon polarizability 13.71 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 3 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 Benzoate degradation via hydroxylation ec00362 1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 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 enterobactin biosynthesis ENTBACSYN-PWY 2,3-dihydroxybenzoate biosynthesis PWY-5901 Specdb::CMs 546 Specdb::CMs 1391 Specdb::CMs 5646 Specdb::CMs 30417 Specdb::CMs 31139 Specdb::CMs 31798 Specdb::CMs 37497 Specdb::CMs 137174 Specdb::CMs 144908 Specdb::CMs 1060433 Specdb::CMs 1060435 Specdb::CMs 1060437 Specdb::CMs 1060438 Specdb::CMs 1060440 Specdb::CMs 1060442 Specdb::CMs 1060444 Specdb::CMs 1060445 Specdb::CMs 1060447 Specdb::CMs 1060449 Specdb::CMs 1060451 Specdb::CMs 1060452 Specdb::CMs 1060454 Specdb::NmrOneD 143710 Specdb::NmrOneD 143711 Specdb::NmrOneD 143712 Specdb::NmrOneD 143713 Specdb::NmrOneD 143714 Specdb::NmrOneD 143715 Specdb::NmrOneD 143716 Specdb::NmrOneD 143717 Specdb::NmrOneD 143718 Specdb::NmrOneD 143719 Specdb::NmrOneD 143720 Specdb::NmrOneD 143721 Specdb::NmrOneD 143722 Specdb::NmrOneD 143723 Specdb::NmrOneD 143724 Specdb::NmrOneD 143725 Specdb::NmrOneD 143726 Specdb::NmrOneD 143727 Specdb::NmrOneD 143728 Specdb::NmrOneD 143729 Specdb::MsMs 603 Specdb::MsMs 604 Specdb::MsMs 605 Specdb::MsMs 240037 Specdb::MsMs 240038 Specdb::MsMs 240039 Specdb::MsMs 242092 Specdb::MsMs 242093 Specdb::MsMs 242094 Specdb::MsMs 439732 Specdb::MsMs 440138 Specdb::MsMs 449821 Specdb::MsMs 449822 Specdb::MsMs 2255333 Specdb::MsMs 2257188 Specdb::MsMs 2257381 Specdb::MsMs 2259225 Specdb::MsMs 2259355 Specdb::MsMs 2365120 Specdb::MsMs 2365121 Specdb::MsMs 2365122 Specdb::MsMs 2597929 Specdb::MsMs 2597930 Specdb::MsMs 2597931 Specdb::NmrTwoD 1297 HMDB00397 18 C00196 18026 2-3-DIHYDROXYBENZOATE DBH Keseler, I. 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Bangladesh Med Res Counc Bull. 1994 Dec;20(3):104-16. 7748148 http://hmdb.ca/system/metabolites/msds/000/000/316/original/HMDB00397.pdf?1358461713 Enterobactin synthase component E P10378 ENTE_ECOLI entE http://ecmdb.ca/proteins/P10378.xml 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase P15047 ENTA_ECOLI entA http://ecmdb.ca/proteins/P15047.xml Blue copper oxidase cueO P36649 CUEO_ECOLI cueO http://ecmdb.ca/proteins/P36649.xml 2-Pyrocatechuic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate DHBAMPLIG-RXN (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 (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD <> 2-Pyrocatechuic acid + NADH + Hydrogen ion R01505 2-Pyrocatechuic acid + Oxygen > Hydrogen ion + 2-Carboxymuconate RXN0-2943 NAD + (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate > Hydrogen ion + NADH + 2-Pyrocatechuic acid DHBDEHYD-RXN Adenosine triphosphate + L-Serine + 2-Pyrocatechuic acid > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + Enterochelin ENTMULTI-RXN 2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2-Pyrocatechuic acid + NADH Adenosine triphosphate + 2-Pyrocatechuic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid Adenosine triphosphate + 2-Pyrocatechuic acid <> Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid R01504 2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2-Pyrocatechuic acid + NADH + Hydrogen ion PW_R002423 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 138.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 552000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 414.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1656000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 274.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1096000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621