2.02012-07-30 14:54:48 -06002015-06-03 17:20:50 -0600ECMDB21185M2MDB001594AerobactinAerobactin 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 acidAerobactinFerric-aerobactinN2,N2'-(3-carboxy-3-hydroxypentanedioyl)bis(N6-acetyl-N6-hydroxy-L-lysine)C22H36N4O13564.5402564.227887258(2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acidaerobactin26198-65-2CC(=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)=OInChI=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/s1KDHHWXGBNUCREU-HOTGVXAUSA-NSolidCytosolExtra-organismPeriplasmlogp-0.98logs-2.48solubility1.86e+00 g/llogp-3pka_strongest_acidic3.02pka_strongest_basic-4.2iupac(2S)-2-[3-carboxy-3-({[(1S)-1-carboxy-5-(N-hydroxyacetamido)pentyl]carbamoyl}methyl)-3-hydroxypropanamido]-6-(N-hydroxyacetamido)hexanoic acidaverage_mass564.5402mono_mass564.227887258smilesCC(=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)=OformulaC22H36N4O13inchiInChI=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/s1inchikeyKDHHWXGBNUCREU-HOTGVXAUSA-Npolar_surface_area271.41refractivity127.26polarizability54.02rotatable_bond_count19acceptor_count13donor_count8physiological_charge-3formal_charge0Specdb::CMs25942Specdb::CMs38696Specdb::CMs282092Specdb::CMs358498Specdb::CMs358499Specdb::CMs358500Specdb::CMs358501Specdb::CMs358502Specdb::CMs358503Specdb::CMs358504Specdb::CMs358505Specdb::CMs358506Specdb::CMs358507Specdb::CMs358508Specdb::CMs358509Specdb::CMs358510Specdb::CMs358511Specdb::CMs358512Specdb::CMs358513Specdb::CMs358514Specdb::CMs358515Specdb::CMs358516Specdb::CMs358517Specdb::CMs358518Specdb::CMs358519Specdb::NmrOneD41382Specdb::NmrOneD41383Specdb::NmrOneD41384Specdb::NmrOneD41385Specdb::NmrOneD41386Specdb::NmrOneD41387Specdb::NmrOneD41388Specdb::NmrOneD41389Specdb::NmrOneD41390Specdb::NmrOneD41391Specdb::NmrOneD41392Specdb::NmrOneD41393Specdb::NmrOneD41394Specdb::NmrOneD41395Specdb::NmrOneD41396Specdb::NmrOneD41397Specdb::NmrOneD41398Specdb::NmrOneD41399Specdb::NmrOneD41400Specdb::NmrOneD41401Specdb::MsMs26222Specdb::MsMs26223Specdb::MsMs26224Specdb::MsMs32780Specdb::MsMs32781Specdb::MsMs32782Specdb::MsMs2384534Specdb::MsMs2384535Specdb::MsMs2384536Specdb::MsMs2577180Specdb::MsMs2577181Specdb::MsMs2577182HMDB04051123762110318C0555418157CPD0-2234AerobactinSharma 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):325-9.1836502Williams 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):942-7.2936686Vazquez 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):110-7.1396724Schlager 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):37-41.10643848Opal 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):794-6.2181035Keller R, Pedroso MZ, Ritchmann R, Silva RM: Occurrence of virulence-associated properties in Enterobacter cloacae. Infect Immun. 1998 Feb;66(2):645-9.9453621Yamamoto S, Shinoda S: [Iron uptake mechanisms of pathogenic bacteria]. Nihon Saikingaku Zasshi. 1996 Feb;51(2):523-47.8752377Iron(3+)-hydroxamate import ATP-binding protein fhuCP07821FHUC_ECOLIfhuChttp://ecmdb.ca/proteins/P07821.xmlIron(3+)-hydroxamate import system permease protein fhuBP06972FHUB_ECOLIfhuBhttp://ecmdb.ca/proteins/P06972.xmlIron(3+)-hydroxamate-binding protein fhuDP07822FHUD_ECOLIfhuDhttp://ecmdb.ca/proteins/P07822.xmlIron(3+)-hydroxamate import ATP-binding protein fhuCP07821FHUC_ECOLIfhuChttp://ecmdb.ca/proteins/P07821.xmlIron(3+)-hydroxamate import system permease protein fhuBP06972FHUB_ECOLIfhuBhttp://ecmdb.ca/proteins/P06972.xmlIron(3+)-hydroxamate-binding protein fhuDP07822FHUD_ECOLIfhuDhttp://ecmdb.ca/proteins/P07822.xmlAdenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Aerobactin > ADP + Aerobactin + Hydrogen ion + PhosphateAerobactin + Fe3+ > AerobactinAerobactin + Fe3+ > Aerobactin