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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:04:58 UTC
Update Date2017-12-07 18:16:07 UTC
HMDB IDHMDB0060881
Secondary Accession Numbers
  • HMDB60881
Metabolite Identification
Common NameDechloroethyl cyclophosphamide
DescriptionDechloroethyl cyclophosphamide 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
DechloroethylcyclophosphamideHMDB
N-(2-Chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxideHMDB
N-(2-Chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amineHMDB
(+-)-Isomer OF dechloroethylcyclophosphamideMeSH
(R)-Isomer OF dechloroethylcyclophosphamideMeSH
N-Dechloroethyl-cpaMeSH
(S)-Isomer OF dechloroethylcyclophosphamideMeSH
3-DCE-iffMeSH
3-DClIFMeSH
Chemical FormulaC5H12ClN2O2P
Average Molecular Weight198.588
Monoisotopic Molecular Weight198.032491857
IUPAC Name2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one
Traditional Name3-dechloroethylifosfamide
CAS Registry NumberNot Available
SMILES
ClCCNP1(=O)NCCCO1
InChI Identifier
InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)
InChI KeyDZKGMGPLDJOVCX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoramides
Direct ParentPhosphoric monoester diamides
Alternative Parents
Substituents
  • Phosphoric monoester diamide
  • Oxazaphosphinane
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility20.3 g/LALOGPS
logP-0.54ALOGPS
logP-0.79ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)12.73ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.24 m³·mol⁻¹ChemAxon
Polarizability17.71 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, Positivesplash10-00di-3900000000-392658bd8725e8f4d2b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-9400000000-da0eda7e219f0430b8a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-9100000000-5d5e6106a794300724afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fafcf55c945ad46ab368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-3900000000-c93fe9c2984f02180ddbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9000000000-505dc81c9537f624df62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9000000000-e80b4317b29aefa564f2View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Cyclophosphamide Action PathwayPw000248Pw000248 greyscalePw000248 simpleNot Available
Cyclophosphamide Metabolism PathwayPw000580Pw000580 greyscalePw000580 simpleNot Available
Ifosfamide Action PathwayPw000249Pw000249 greyscalePw000249 simpleNot Available
Ifosfamide Metabolism PathwayPw000581Pw000581 greyscalePw000581 simpleNot Available
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID102819
      KEGG Compound IDC16550
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound114861
      PDB IDNot Available
      ChEBI ID238115
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available