Record Information
Version2.0
Creation Date2012-07-30 14:55:20 -0600
Update Date2015-06-03 17:21:10 -0600
Secondary Accession Numbers
  • ECMDB21332
Identification
Name:ferroxamine minus Fe(3)
DescriptionFerrioxamine 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:
  • N-5-4-5-acetyl(hydroxy)aminopentylamino-4-oxobutanoyl-hydroxyaminopentyl-N'-(5-aminopentyl)-N'-hydroxybutanediamide; iron(3+)
Chemical Formula:C25H48FeN6O8
Weight:Average: 616.529
Monoisotopic: 616.288304675
InChI Key:BLMKUGGNEDBRRA-UHFFFAOYSA-N
InChI:InChI=1S/C25H48N6O8.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;/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);/q;+3
CAS number:Not Available
IUPAC Name:iron(3+) ion 3-[(5-aminopentyl)(hydroxy)carbamoyl]-N-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]-C-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid
Traditional IUPAC Name:iron(3+) ion deferoxamine
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
  • Acetohydroxamic acid
  • Amino acid or derivatives
  • Carboxamide group
  • Hydroxamic acid
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic transition metal salt
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic salt
  • Amine
  • Organic cation
  • 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
logP-2.6ChemAxon
pKa (Strongest Acidic)7ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area212.82 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity145.99 m³·mol⁻¹ChemAxon
Polarizability63.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
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 IDNot Available
Pubchem Compound ID441292
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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