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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:11:56 UTC
HMDB IDHMDB0014884
Secondary Accession Numbers
  • HMDB14884
Metabolite Identification
Common NameDeferoxamine
DescriptionDeferoxamine is only found in individuals that have used or taken this drug. It is a natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form. [PubChem]Deferoxamine works in treating iron toxicity by binding trivalent (ferric) iron (for which it has a strong affinity), forming ferrioxamine, a stable complex which is eliminated via the kidneys. 100 mg of deferoxamine is capable of binding approximately 8.5 mg of trivalent (ferric) iron. Deferoxamine works in treating aluminum toxicity by binding to tissue-bound aluminum to form aluminoxamine, a stable, water-soluble complex. The formation of aluminoxamine increases blood concentrations of aluminum, resulting in an increased concentration gradient between the blood and dialysate, boosting the removal of aluminum during dialysis. 100 mg of deferoxamine is capable of binding approximately 4.1 mg of aluminum.
Structure
Thumb
Synonyms
ValueSource
DeferoxaminChEBI
DeferoxaminaChEBI
DeferoxaminumChEBI
DeferrioxamineChEBI
Deferrioxamine bChEBI
DesferrioxamineChEBI
DFOChEBI
Deferoxamide bHMDB
Deferoxamine bHMDB
Desferrioxamine bHMDB
DF bHMDB
DFOAHMDB
DFOMHMDB
N-Benzoylferrioxamine bHMDB
b, DeferoxamineMeSH
Deferoxamine mesylateMeSH
DeferoximineMeSH
DesferioximineMeSH
Desferrioxamine b mesylateMeSH
Mesylate, deferoxamineMeSH
Deferoxamine methanesulfonateMeSH
Mesylate, desferrioxamine bMeSH
Methanesulfonate, deferoxamineMeSH
b, DesferrioxamineMeSH
DesferalMeSH
Mesilate, deferoxamineMeSH
Deferoxamine mesilateMeSH
DesferroxamineMeSH
Chemical FormulaC25H48N6O8
Average Molecular Weight560.684
Monoisotopic Molecular Weight560.353362542
IUPAC NameN-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide
Traditional NameN-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]succinamide
CAS Registry Number70-51-9
SMILES
CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
InChI Identifier
InChI=1S/C25H48N6O8/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)
InChI KeyUBQYURCVBFRUQT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetohydroxamic acids
Alternative Parents
Substituents
  • Acetamide
  • Acetohydroxamic acid
  • Amino acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.099 g/LNot Available
LogP-2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.099 g/LALOGPS
logP0.93ALOGPS
logP-3.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area205.84 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity144.95 m³·mol⁻¹ChemAxon
Polarizability62.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uyu-9351600000-db7e9dcd06da7cb8ce44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Hybrid FT , Positivesplash10-00di-2901000023-e1b4c2a4d54a44d851b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-Hybrid FT , Positivesplash10-0007-9621400000-89d305f0c72708d1a2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udl-0892110000-487a5822b41da03f0948View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-05ne-1943110000-cfdaf16ce07341d78b59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udl-0892110000-487a5822b41da03f0948View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0007-9621400000-9b6a525f53e7f320f714View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ikc-1771190000-39b4db7f6f66f4b9474eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0111190000-7dabe399b61bdc270ec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0914140000-564eef1c4ca4057e0567View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-3912000000-9d41fb6ae4247de66ef2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-4911000000-7819a57b67abf35540d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-3141590000-a67788337266f4e2e5e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bc-6675890000-824c1c1e5fffa6d72d90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-7977400000-661b6336ef20e2b1ba69View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00746 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00746 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00746
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2867
KEGG Compound IDC06940
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeferoxamine
METLIN IDNot Available
PubChem Compound2973
PDB IDNot Available
ChEBI ID4356
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. MedlinePlus [Link]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Rinaldo JE, Gorry M: Protection by deferoxamine from endothelial injury: a possible link with inhibition of intracellular xanthine oxidase. Am J Respir Cell Mol Biol. 1990 Dec;3(6):525-33. [PubMed:2252579 ]