2.0 2012-07-30 14:54:58 -0600 2015-06-03 17:20:54 -0600 ECMDB21212 M2MDB001620 Enterochelin Enterobactin (also known as Enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium. (3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide) Enterobactin Enterochelin H6ent N,N',N''-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide) Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester C30H27N3O15 669.5465 669.144217209 N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide enterobactin 28384-96-5 OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1 SERBHKJMVBATSJ-BZSNNMDCSA-N Cytosol Extra-organism Membrane Periplasm logp 1.62 ALOGPS logs -3.82 ALOGPS solubility 1.00e-01 g/l ALOGPS logp 2.26 ChemAxon pka_strongest_acidic 7.82 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide ChemAxon average_mass 669.5465 ChemAxon mono_mass 669.144217209 ChemAxon smiles OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O ChemAxon formula C30H27N3O15 ChemAxon inchi InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1 ChemAxon inchikey SERBHKJMVBATSJ-BZSNNMDCSA-N ChemAxon polar_surface_area 287.58 ChemAxon refractivity 157.87 ChemAxon polarizability 61.87 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 12 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 enterobactin biosynthesis ENTBACSYN-PWY Specdb::CMs 21119 Specdb::CMs 701671 Specdb::CMs 701672 Specdb::CMs 701673 Specdb::CMs 701674 Specdb::CMs 701675 Specdb::CMs 701676 Specdb::CMs 701677 Specdb::CMs 701678 Specdb::CMs 701679 Specdb::CMs 701680 Specdb::CMs 701681 Specdb::CMs 701682 Specdb::CMs 701683 Specdb::CMs 701684 Specdb::CMs 701685 Specdb::CMs 701686 Specdb::CMs 701687 Specdb::CMs 701688 Specdb::CMs 701689 Specdb::CMs 701690 Specdb::CMs 701691 Specdb::CMs 701692 Specdb::CMs 701693 Specdb::CMs 701694 Specdb::MsMs 26417 Specdb::MsMs 26418 Specdb::MsMs 26419 Specdb::MsMs 32975 Specdb::MsMs 32976 Specdb::MsMs 32977 Specdb::MsMs 2697390 Specdb::MsMs 2697391 Specdb::MsMs 2697392 Specdb::MsMs 2982059 Specdb::MsMs 2982060 Specdb::MsMs 2982061 34231 31543 C05821 28855 ENTEROBACTIN EB4 Enterochelin 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 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 Enterobactin synthase component F P11454 ENTF_ECOLI entF http://ecmdb.ca/proteins/P11454.xml Enterochelin esterase P13039 FES_ECOLI fes http://ecmdb.ca/proteins/P13039.xml 4'-phosphopantetheinyl transferase entD P19925 ENTD_ECOLI entD http://ecmdb.ca/proteins/P19925.xml Enterobactin exporter entS P24077 ENTS_ECOLI entS http://ecmdb.ca/proteins/P24077.xml Outer membrane protein tolC P02930 TOLC_ECOLI tolC http://ecmdb.ca/proteins/P02930.xml 3 (2,3-Dihydroxybenzoyl)adenylic acid + 3 L-Seryl-AMP >6 Adenosine monophosphate + Enterochelin +9 Hydrogen ion ENTG-RXN Enterochelin + 3 Water >3 2,3-Dihydroxybenzoylserine +3 Hydrogen ion RXN0-1661 Enterochelin + Fe3+ > Ferric enterobactin (2,3-Dihydroxybenzoyl)adenylic acid + L-Seryl-AMP <> Hydrogen ion + Enterochelin + Adenosine monophosphate ENTG-RXN Enterochelin + Water > Hydrogen ion + 2,3-Dihydroxybenzoylserine RXN0-1661 Adenosine triphosphate + L-Serine + 2-Pyrocatechuic acid > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + Enterochelin ENTMULTI-RXN 3 a DHB-seryl-[EntF peptidyl-carrier protein] > Enterochelin +3 a holo-[EntF peptidyl-carrier protein] PW_R005982