2.0 2012-07-30 14:54:48 -0600 2015-06-03 17:20:50 -0600 ECMDB21185 M2MDB001594 Aerobactin Aerobactin is a iron chelating agent (siderophore) found in bacteria such as E. coli, allowing bacteria to transport and sequester iron. It is a virulence factor enabling E. coli to sequester iron in iron-poor environments such as host urinary tracts. (Wikipedia, ChEBI) Aerobactin can be made in E. coli through the degradation of lysine by the enzyme aerobactin synthase (EC 6.3.2.27). (Wikipedia, KEGG) (8S,16S)-3,12,21-trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylate (8S,16S)-3,12,21-trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acid Aerobactin Ferric-aerobactin N2,N2'-(3-carboxy-3-hydroxypentanedioyl)bis(N6-acetyl-N6-hydroxy-L-lysine) C22H36N4O13 564.5402 564.227887258 (2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid aerobactin 26198-65-2 CC(=O)N(O)CCCC[C@H](NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(C)=O)C(O)=O)C(O)=O)C(O)=O InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 KDHHWXGBNUCREU-HOTGVXAUSA-N Solid Cytosol Extra-organism Periplasm logp -0.98 ALOGPS logs -2.48 ALOGPS solubility 1.86e+00 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 3.02 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acid ChemAxon average_mass 564.5402 ChemAxon mono_mass 564.227887258 ChemAxon smiles CC(=O)N(O)CCCC[C@H](NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(C)=O)C(O)=O)C(O)=O)C(O)=O ChemAxon formula C22H36N4O13 ChemAxon inchi InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 ChemAxon inchikey KDHHWXGBNUCREU-HOTGVXAUSA-N ChemAxon polar_surface_area 271.41 ChemAxon refractivity 127.26 ChemAxon polarizability 54.02 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25942 Specdb::CMs 38696 Specdb::CMs 282092 Specdb::CMs 358498 Specdb::CMs 358499 Specdb::CMs 358500 Specdb::CMs 358501 Specdb::CMs 358502 Specdb::CMs 358503 Specdb::CMs 358504 Specdb::CMs 358505 Specdb::CMs 358506 Specdb::CMs 358507 Specdb::CMs 358508 Specdb::CMs 358509 Specdb::CMs 358510 Specdb::CMs 358511 Specdb::CMs 358512 Specdb::CMs 358513 Specdb::CMs 358514 Specdb::CMs 358515 Specdb::CMs 358516 Specdb::CMs 358517 Specdb::CMs 358518 Specdb::CMs 358519 Specdb::NmrOneD 41382 Specdb::NmrOneD 41383 Specdb::NmrOneD 41384 Specdb::NmrOneD 41385 Specdb::NmrOneD 41386 Specdb::NmrOneD 41387 Specdb::NmrOneD 41388 Specdb::NmrOneD 41389 Specdb::NmrOneD 41390 Specdb::NmrOneD 41391 Specdb::NmrOneD 41392 Specdb::NmrOneD 41393 Specdb::NmrOneD 41394 Specdb::NmrOneD 41395 Specdb::NmrOneD 41396 Specdb::NmrOneD 41397 Specdb::NmrOneD 41398 Specdb::NmrOneD 41399 Specdb::NmrOneD 41400 Specdb::NmrOneD 41401 Specdb::MsMs 26222 Specdb::MsMs 26223 Specdb::MsMs 26224 Specdb::MsMs 32780 Specdb::MsMs 32781 Specdb::MsMs 32782 Specdb::MsMs 2384534 Specdb::MsMs 2384535 Specdb::MsMs 2384536 Specdb::MsMs 2577180 Specdb::MsMs 2577181 Specdb::MsMs 2577182 HMDB04051 123762 110318 C05554 18157 CPD0-2234 Aerobactin Sharma S, Harjai K, Mittal R: Enhanced siderophore production and mouse kidney pathogenicity in Escherichia coli grown in urine. J Med Microbiol. 1991 Dec;35(6):325-9. 1836502 Williams PH, Carbonetti NH: Iron, siderophores, and the pursuit of virulence: independence of the aerobactin and enterochelin iron uptake systems in Escherichia coli. Infect Immun. 1986 Mar;51(3):942-7. 2936686 Vazquez F, Mendoza MC, Viejo G, Mendez FJ: Survey of Escherichia coli septicemia over a six-year period. Eur J Clin Microbiol Infect Dis. 1992 Feb;11(2):110-7. 1396724 Schlager TA, Whittam TS, Hendley JO, Wilson RA, Bhang J, Grady R, Stapleton A: Expression of virulence factors among Escherichia coli isolated from the periurethra and urine of children with neurogenic bladder on intermittent catheterization. Pediatr Infect Dis J. 2000 Jan;19(1):37-41. 10643848 Opal SM, Cross AS, Gemski P, Lyhte LW: Aerobactin and alpha-hemolysin as virulence determinants in Escherichia coli isolated from human blood, urine, and stool. J Infect Dis. 1990 Apr;161(4):794-6. 2181035 Keller R, Pedroso MZ, Ritchmann R, Silva RM: Occurrence of virulence-associated properties in Enterobacter cloacae. Infect Immun. 1998 Feb;66(2):645-9. 9453621 Yamamoto S, Shinoda S: [Iron uptake mechanisms of pathogenic bacteria]. Nihon Saikingaku Zasshi. 1996 Feb;51(2):523-47. 8752377 Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Adenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + Phosphate Aerobactin + Fe3+ > Aerobactin Aerobactin + Fe3+ > Aerobactin