<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:22:42 UTC</creation_date>
  <update_date>2026-08-22 05:38:20 UTC</update_date>
  <accession/>
  <common_name>Deferoxamine</common_name>
  <class>SmallMolecule</class>
  <description>Deferoxamine (C25H48N6O8) is a compound that functions biologically as a siderophore, an iron chelator (PMC4507282), and a chelator (PMC10855613). Deferoxamine belongs to the carboxylic acid derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 560.68 g/mol, Deferoxamine is a heavy molecule. It acts as a downregulator of the protein target Amyloid-beta precursor protein (APP).

The compound is found in or released from 18 recorded sources, including food preservation, unclassified therapeutic products, stairs and ramps, and household cleaning and consumer products such as soap detergents, bleaching agents, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with electrical and electronic equipment, including electric switches, electrically stimulated smoking devices, electric hearing aids, and conductors or conductive bodies characterised by the conductive materials, cores yokes or armatures. Recorded exposure routes include subcutaneous, intravenous, intraperitoneal, and intramuscular administration, while literature supports inhalation as an exposure route (PMC3359900).

In terms of health effects, Deferoxamine is used as a treatment for ischemic stroke (PMC8913707) and hemochromatosis (PMC11308372). It has a therapeutic effect on pulmonary fibrosis (PMC13006651) but is associated with anemia (PMC5384363).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C25H48N6O8</chemical_formula>
  <average_molecular_weight>560.684</average_molecular_weight>
  <monisotopic_moleculate_weight>560.353362542</monisotopic_moleculate_weight>
  <iupac_name>N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide</iupac_name>
  <traditional_iupac>N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]succinamide</traditional_iupac>
  <cas_registry_number>70-51-9</cas_registry_number>
  <smiles>CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN</smiles>
  <inchi>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>
  <inchikey>UBQYURCVBFRUQT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acid derivatives</sub_class>
    <direct_parent>Acetohydroxamic acids</direct_parent>
    <alternate_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acetohydroxamic acid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>a hydroxamate siderophore</descriptor>
      <descriptor>acyclic desferrioxamine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Deferoxamine Drug Metabolism</name>
      <smpdb_id>SMP0130854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Deferoxamine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143189</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.90e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>560.684</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>560.353362542</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H48N6O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UBQYURCVBFRUQT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>205.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>62.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf3799880&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00746</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>2973</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2867</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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    <target>
      <target_id>BE0003392</target_id>
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  </targets>
</compound>
