2.0 2012-05-31 14:03:38 -0600 2015-06-03 15:54:41 -0600 ECMDB04053 M2MDB000585 (2,3-Dihydroxybenzoyl)adenylic acid (2,3-dihydroxybenzoyl)adenylate is a member of the chemical class known as Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. (2,3-Dihydroxybenzoyl)adenylate 2,3-Dihydroxybenzoyl adenylate 2,3-Dihydroxybenzoyl adenylic acid C17H18N5O10P 483.3261 483.079128333 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(2,3-dihydroxybenzoyloxy)phosphinic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid [H][C@]1(COP(O)(=O)OC(=O)C2=C(O)C(O)=CC=C2)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O InChI=1S/C17H18N5O10P/c18-14-10-15(20-5-19-14)22(6-21-10)16-13(26)12(25)9(31-16)4-30-33(28,29)32-17(27)7-2-1-3-8(23)11(7)24/h1-3,5-6,9,12-13,16,23-26H,4H2,(H,28,29)(H2,18,19,20)/t9-,12-,13-,16-/m1/s1 ULPVJDOMCRTJSN-RVXWVPLUSA-N Cytosol logp -0.59 ALOGPS logs -2.43 ALOGPS solubility 1.78e+00 g/l ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 0.78 ChemAxon pka_strongest_basic 4.99 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(2,3-dihydroxybenzoyloxy)phosphinic acid ChemAxon average_mass 483.3261 ChemAxon mono_mass 483.079128333 ChemAxon smiles [H][C@]1(COP(O)(=O)OC(=O)C2=C(O)C(O)=CC=C2)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O ChemAxon formula C17H18N5O10P ChemAxon inchi InChI=1S/C17H18N5O10P/c18-14-10-15(20-5-19-14)22(6-21-10)16-13(26)12(25)9(31-16)4-30-33(28,29)32-17(27)7-2-1-3-8(23)11(7)24/h1-3,5-6,9,12-13,16,23-26H,4H2,(H,28,29)(H2,18,19,20)/t9-,12-,13-,16-/m1/s1 ChemAxon inchikey ULPVJDOMCRTJSN-RVXWVPLUSA-N ChemAxon polar_surface_area 232.6 ChemAxon refractivity 107.85 ChemAxon polarizability 42.45 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 12 ChemAxon donor_count 6 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 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 Specdb::CMs 1085160 Specdb::EiMs 2144 Specdb::NmrOneD 322692 Specdb::NmrOneD 322693 Specdb::NmrOneD 322694 Specdb::NmrOneD 322695 Specdb::NmrOneD 322696 Specdb::NmrOneD 322697 Specdb::NmrOneD 322698 Specdb::NmrOneD 322699 Specdb::NmrOneD 322700 Specdb::NmrOneD 322701 Specdb::NmrOneD 322702 Specdb::NmrOneD 322703 Specdb::NmrOneD 322704 Specdb::NmrOneD 322705 Specdb::NmrOneD 322706 Specdb::NmrOneD 322707 Specdb::NmrOneD 322708 Specdb::NmrOneD 322709 Specdb::NmrOneD 322710 Specdb::NmrOneD 322711 Specdb::MsMs 29003 Specdb::MsMs 29004 Specdb::MsMs 29005 Specdb::MsMs 35561 Specdb::MsMs 35562 Specdb::MsMs 35563 440201 389188 C04030 5572 CPD-62 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 Isochorismatase P0ADI4 ENTB_ECOLI entB http://ecmdb.ca/proteins/P0ADI4.xml Enterobactin synthase component E P10378 ENTE_ECOLI entE http://ecmdb.ca/proteins/P10378.xml Enterobactin synthase component F P11454 ENTF_ECOLI entF http://ecmdb.ca/proteins/P11454.xml 4'-phosphopantetheinyl transferase entD P19925 ENTD_ECOLI entD http://ecmdb.ca/proteins/P19925.xml 3 (2,3-Dihydroxybenzoyl)adenylic acid + 3 L-Seryl-AMP >6 Adenosine monophosphate + Enterochelin +9 Hydrogen ion ENTG-RXN 2-Pyrocatechuic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate DHBAMPLIG-RXN (2,3-Dihydroxybenzoyl)adenylic acid + L-Seryl-AMP <> Hydrogen ion + Enterochelin + Adenosine monophosphate ENTG-RXN Adenosine triphosphate + 2-Pyrocatechuic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid (2,3-Dihydroxybenzoyl)adenylic acid + holo-entB > Adenosine monophosphate + acyl-holo-entB Adenosine triphosphate + 2-Pyrocatechuic acid <> Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid R01504 Adenosine triphosphate + 2,3-Dihydroxybenzoic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid PW_R005259 Adenosine triphosphate + 2,3-Dihydroxybenzoic acid <> (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate PW_R005260 2,3-Dihydroxybenzoic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate PW_R005979 (2,3-Dihydroxybenzoyl)adenylic acid + a holo-[EntB isochorismatase/aryl-carrier protein] > a 2,3-dihydroxybenzoyl-[EntB isochorismatase/aryl-carrier protein] + Adenosine monophosphate + Hydrogen ion PW_R005980