Record Information
Version2.0
Creation Date2012-07-30 14:55:20 -0600
Update Date2015-06-03 17:21:11 -0600
Secondary Accession Numbers
  • ECMDB21333
Identification
Name:Ferroxamine
DescriptionFerroxamine 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)
Structure
Thumb
Synonyms:
  • Desferal-iron(III)
  • Ferrioxamine
Chemical Formula:C25H45FeN6O8
Weight:Average: 613.505
Monoisotopic: 613.264829579
InChI Key:SRMBQCVUAVULDJ-UHFFFAOYSA-N
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
CAS number:14836-73-8
IUPAC Name:Not Available
Traditional IUPAC Name:Not Available
SMILES:[Fe+3].CC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Acetamide
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic transition metal salt
  • Organic salt
  • Organic zwitterion
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP1.17ALOGPS
logS-3.1ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area224.05 ŲChemAxon
Polarizability61.65 ųChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1000039000-9a08c3b4b0475f3f94e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vt-4000093000-dd4ce26cefdff59b662cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000010000-2d474c6ddd3d5c60c828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000079000-325f8d68e881dcb024baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ml-2000193000-5800de7b99b53db70363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00c3-9000020000-2818bb4ba0d3340358f3View in MoNA
References
References:
  • Matzanke, B. F., Anemuller, S., Schunemann, V., Trautwein, A. X., Hantke, K. (2004). "FhuF, part of a siderophore-reductase system." Biochemistry 43:1386-1392. Pubmed: 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. Pubmed: 11489851
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0240270
Pubchem Compound ID123851
Kegg IDC07597
ChemSpider ID110391
Wikipedia IDNot Available
BioCyc IDCPD0-2124
EcoCyc IDCPD0-2124

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Involved in the reduction of ferric iron in cytoplasmic ferrioxamine B
Gene Name:
fhuF
Uniprot ID:
P39405
Molecular weight:
30113
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
General function:
Involved in receptor activity
Specific function:
This receptor binds the ferrichrome-iron ligand. It interacts with the tonB protein, which is responsible for energy coupling of the ferrichrome-promoted iron transport system. Acts as a receptor for bacteriophage T5 as well as T1, phi80 and colicin M. Binding of T5 triggers the opening of a high conductance ion channel. Can also transport the antibiotic albomycin
Gene Name:
fhuA
Uniprot ID:
P06971
Molecular weight:
82182
General function:
Involved in protein transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates. Protects exbD from proteolytic degradation and functionally stabilizes tonB
Gene Name:
exbB
Uniprot ID:
P0ABU7
Molecular weight:
26287
General function:
Involved in transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates
Gene Name:
exbD
Uniprot ID:
P0ABV2
Molecular weight:
15527
General function:
Involved in iron ion transmembrane transporter activity
Specific function:
Interacts with outer membrane receptor proteins that carry out high-affinity binding and energy dependent uptake into the periplasmic space of specific substrates such as cobalamin, and various iron compounds (such as iron dicitrate, enterochelin, aerobactin, etc.). In the absence of tonB these receptors bind their substrates but do not carry out active transport. TonB also interacts with some colicins and is involved in the energy- dependent, irreversible steps of bacteriophages phi 80 and T1 infection. It could act to transduce energy from the cytoplasmic membrane to specific energy-requiring processes in the outer membrane, resulting in the release into the periplasm of ligands bound by these outer membrane proteins
Gene Name:
tonB
Uniprot ID:
P02929
Molecular weight:
26094
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998