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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:20 -0600
Update Date	2015-06-03 17:21:10 -0600
Secondary Accession Numbers	ECMDB21332
Identification
Name:	ferroxamine minus Fe(3)
Description	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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa93650d4> Close
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty amides
Direct Parent	N-acyl amines
Alternative Parents	Acetohydroxamic acids Acetamides Secondary carboxylic acid amides Amino acids and derivatives Organic transition metal salts Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds Organic cations
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 Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source logP -2.6 ChemAxon pKa (Strongest Acidic) 7 ChemAxon pKa (Strongest Basic) 10.23 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 212.82 Ų ChemAxon Rotatable Bond Count 23 ChemAxon Refractivity 145.99 m³·mol⁻¹ ChemAxon Polarizability 63.42 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	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
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 441292 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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