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Record Information
Version4.0
Creation Date2013-06-18 18:55:11 UTC
Update Date2017-09-27 08:43:52 UTC
HMDB IDHMDB0060686
Secondary Accession Numbers
  • HMDB60686
Metabolite Identification
Common Name4-Ketocyclophosphamide
Description4-Ketocyclophosphamide is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-Ketocyclophosphamide, (S)-isomerMeSH
4-Ketocyclophosphamide, (R)-isomerMeSH
Chemical FormulaC7H13Cl2N2O3P
Average Molecular Weight275.069
Monoisotopic Molecular Weight274.004084218
IUPAC Name2-[bis(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione
Traditional Name2-[bis(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione
CAS Registry NumberNot Available
SMILES
ClCCN(CCCl)P1(=O)NC(=O)CCO1
InChI Identifier
InChI=1S/C7H13Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h1-6H2,(H,10,12,13)
InChI KeyVBMZHOCORXMDJU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Organic phosphoric acid derivative
  • Organic phosphoric acid amide
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl halide
  • 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 Solubility14.3 g/LALOGPS
logP0.15ALOGPS
logP-0.089ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.64 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.39 m³·mol⁻¹ChemAxon
Polarizability23.83 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Cyclophosphamide Metabolism PathwayPw000580Pw000580 greyscalePw000580 simpleNot Available
Cyclophosphamide PathwayPw000248Pw000248 greyscalePw000248 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 IDC07644
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID1887
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available