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Record Information
Version2.0
Created at2022-09-12 05:01:34 UTC
Updated at2022-09-12 05:01:34 UTC
NP-MRD IDNP0324755
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid
DescriptionDeferoxamine, also known as DFO or DF b, 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. Thus, deferoxamine is considered to be a fatty amide lipid molecule. Deferoxamine is a drug which is used to treat acute iron or aluminum toxicity (an excess of aluminum in the body) in certain patients. Also used in certain patients with anemia who must receive many blood transfusions. Deferoxamine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is unclear if use during pregnancy or breastfeeding is safe for the baby. It is used by injection into a muscle, vein, or under the skin. 3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid is found in Streptomyces albidoflavus, Streptomyces argillaceus, Streptomyces coelicolor, Streptomyces griseus, Streptomyces hebeiensis, Streptomyces lydicus, Streptomyces malaysiense, Streptomyces mirabilis, Streptomyces parvulus, Streptomyces pilosus and Streptomyces wadayamensis. Apart from iron toxicity, deferoxamine can be used to treat aluminium toxicity (an excess of aluminium in the body) in select patients.
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, DeferoxamineHMDB
Deferoxamine mesylateHMDB
DeferoximineHMDB
DesferioximineHMDB
Desferrioxamine b mesylateHMDB
Mesylate, deferoxamineHMDB
Deferoxamine methanesulfonateHMDB
Mesylate, desferrioxamine bHMDB
Methanesulfonate, deferoxamineHMDB
b, DesferrioxamineHMDB
DesferalHMDB
Mesilate, deferoxamineHMDB
Deferoxamine mesilateHMDB
DesferroxamineHMDB
Chemical FormulaC25H48N6O8
Average Mass560.6840 Da
Monoisotopic Mass560.35336 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces albidoflavusLOTUS Database
Streptomyces argillaceusLOTUS Database
Streptomyces coelicolorLOTUS Database
Streptomyces griseusLOTUS Database
Streptomyces hebeiensisLOTUS Database
Streptomyces lydicusLOTUS Database
Streptomyces malaysienseLOTUS Database
Streptomyces mirabilisLOTUS Database
Streptomyces parvulusLOTUS Database
Streptomyces pilosusLOTUS Database
Streptomyces wadayamensisLOTUS Database
Chemical Taxonomy
Description 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014884
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
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]