2.0 2012-07-30 14:55:20 -0600 2015-06-03 17:21:11 -0600 ECMDB21333 M2MDB001734 Ferroxamine Ferroxamine is a member of the chemical class known as Hydroxamic Acids. These are compounds containing an hydroxamic acid functional group in which an hydroxylamine is inserted into a carboxylic acid. Its general structure is R-CO-NH-OH, with an R as an organic residue. Ferrioxamine is catalyzed by fhuF. The phenotype of fhuF mutants and the structural features of the FhuF protein suggest that FhuF is involved in the reduction of ferric iron in cytoplasmic ferrioxamine B. (PMID 9990318) Insertional inactivation and gene replacement of both genes showed that while FhuD2 is involved in the transport of iron(III) in complex with ferrichrome, ferrioxamine B, aerobactin, and coprogen. FhuD1 shows a more limited substrate range, capable of only iron(III)-ferrichrome and iron(III)-ferrioxamine B transport in S. (PMID 11489851) Removal of iron from coprogen, ferrichrome, and ferrioxamine B was significantly lower in fhuF mutants compared to the corresponding parental strains, which suggested that FhuF is involved in iron removal from these hydroxamate-type siderophores. (PMID 14756576) Desferal-iron(III) Ferrioxamine C25H45FeN6O8 613.505 613.264829579 14836-73-8 [Fe+3].CC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN InChI=1S/C25H45N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h2-20,26H2,1H3,(H,27,33)(H,28,34);/q-3;+3 SRMBQCVUAVULDJ-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp 1.17 ALOGPS logs -3.15 ALOGPS solubility 4.35e-01 g/l ALOGPS pka_strongest_acidic 13.79 ChemAxon pka_strongest_basic 9.61 ChemAxon average_mass 613.505 ChemAxon mono_mass 613.264829579 ChemAxon smiles [Fe+3].CC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN ChemAxon formula C25H45FeN6O8 ChemAxon inchi InChI=1S/C25H45N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h2-20,26H2,1H3,(H,27,33)(H,28,34);/q-3;+3 ChemAxon inchikey SRMBQCVUAVULDJ-UHFFFAOYSA-N ChemAxon polar_surface_area 224.05 ChemAxon polarizability 61.65 ChemAxon acceptor_count 12 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1088494 Specdb::EiMs 2109 Specdb::MsMs 1294417 Specdb::MsMs 1294418 Specdb::MsMs 1294419 Specdb::MsMs 1409077 Specdb::MsMs 1409078 Specdb::MsMs 1409079 Specdb::MsMs 2467499 Specdb::MsMs 2467500 Specdb::MsMs 2467501 Specdb::MsMs 2498645 Specdb::MsMs 2498646 Specdb::MsMs 2498647 123851 110391 C07597 CPD0-2124 Matzanke, B. F., Anemuller, S., Schunemann, V., Trautwein, A. X., Hantke, K. (2004). "FhuF, part of a siderophore-reductase system." Biochemistry 43:1386-1392. 14756576 Sebulsky, M. T., Heinrichs, D. E. (2001). "Identification and characterization of fhuD1 and fhuD2, two genes involved in iron-hydroxamate uptake in Staphylococcus aureus." J Bacteriol 183:4994-5000. 11489851 Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Ferric iron reductase protein fhuF P39405 FHUF_ECOLI fhuF http://ecmdb.ca/proteins/P39405.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 Ferrichrome-iron receptor P06971 FHUA_ECOLI fhuA http://ecmdb.ca/proteins/P06971.xml Biopolymer transport protein exbB P0ABU7 EXBB_ECOLI exbB http://ecmdb.ca/proteins/P0ABU7.xml Biopolymer transport protein exbD P0ABV2 EXBD_ECOLI exbD http://ecmdb.ca/proteins/P0ABV2.xml Protein tonB P02929 TONB_ECOLI tonB http://ecmdb.ca/proteins/P02929.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Adenosine triphosphate + Water + Ferroxamine > ADP + Ferroxamine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Ferroxamine > ADP + Ferroxamine + Hydrogen ion + Phosphate FADH2 + 2 Ferroxamine > FAD +2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion 2 Ferroxamine + FMNH >2 Iron +2 ferroxamine minus Fe(3) + Flavin Mononucleotide +2 Hydrogen ion 2 Ferroxamine + Reduced riboflavin >2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion + Riboflavin Fe3+ + ferroxamine minus Fe(3) > Ferroxamine