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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-18 19:13:49 UTC
Update Date2017-10-23 19:15:46 UTC
HMDB IDHMDB0060690
Secondary Accession Numbers
  • HMDB60690
Metabolite Identification
Common Name4-Ketoifosfamide
Description4-Ketoifosfamide is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated 'IFO'. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-Ketoifosfamide, (S)-isomerMeSH
Chemical FormulaC7H13Cl2N2O3P
Average Molecular Weight275.069
Monoisotopic Molecular Weight274.004084218
IUPAC Name3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione
Traditional Name4-ketoifosfamide
CAS Registry NumberNot Available
SMILES
ClCCNP1(=O)OCCC(=O)N1CCCl
InChI Identifier
InChI=1S/C7H13Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h1-6H2,(H,10,13)
InChI KeyPEZLCTIXHCOEOG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxazaphosphinanes
Direct ParentIsofamides
Alternative Parents
Substituents
  • Isofamide
  • Organic phosphoric acid derivative
  • Organic phosphoric acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Alkyl chloride
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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
Water Solubility13 g/LALOGPS
logP0.08ALOGPS
logP-0.089ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.64 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.39 m³·mol⁻¹ChemAxon
Polarizability24.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-03g1-4890000000-70b09f3838e2ec71629dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9020000000-61b100347818e415b7a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-1913777d6533a9470ec5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-55575a2a20e4b5270778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3790000000-65c483ba55dc262acdb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-8900000000-d416672ac210c11662ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9000000000-bebe75fba33a4f3c3605View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Ifosfamide Metabolism PathwayPw000581Pw000581 greyscalePw000581 simpleNot Available
Ifosfamide PathwayPw000249Pw000249 greyscalePw000249 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16554
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID80561
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available