Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:55:11 UTC
Update Date2019-07-23 07:14:51 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
Data?1563866091
Synonyms
ValueSource
4-Ketocyclophosphamide, (S)-isomerHMDB
4-Ketocyclophosphamide, (R)-isomerHMDB
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
Description Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard 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
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+152.94430932474
DeepCCS[M-H]-149.34730932474
DeepCCS[M-2H]-186.07730932474
DeepCCS[M+Na]+161.7430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-KetocyclophosphamideClCCN(CCCl)P1(=O)NC(=O)CCO13132.3Standard polar33892256
4-KetocyclophosphamideClCCN(CCCl)P1(=O)NC(=O)CCO12047.9Standard non polar33892256
4-KetocyclophosphamideClCCN(CCCl)P1(=O)NC(=O)CCO12190.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Ketocyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2090.8Semi standard non polar33892256
4-Ketocyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2124.4Standard non polar33892256
4-Ketocyclophosphamide,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2864.8Standard polar33892256
4-Ketocyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2354.4Semi standard non polar33892256
4-Ketocyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2388.6Standard non polar33892256
4-Ketocyclophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCOP1(=O)N(CCCl)CCCl2982.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ketocyclophosphamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q0-3960000000-d4ee69c4b1af29ee0b792017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ketocyclophosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Positive-QTOFsplash10-0a6r-9150000000-a5fe23eb32924f1c101d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Positive-QTOFsplash10-006x-9800000000-6de17123e0f5162e9a8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Positive-QTOFsplash10-0bvi-9000000000-99792497718e2c066f202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Negative-QTOFsplash10-03di-1690000000-0ae369eead37fb2bb6ea2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Negative-QTOFsplash10-00dl-9000000000-ffa9969f204bd6d68bb82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Negative-QTOFsplash10-0007-9000000000-7c9a945230dd65d33ef42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Positive-QTOFsplash10-004i-1490000000-06cf3f86b8a2918caea12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Positive-QTOFsplash10-057i-2940000000-bd20f30390805f5f11c72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Positive-QTOFsplash10-03di-9200000000-46a634ff820fbda1e6db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 10V, Negative-QTOFsplash10-00di-0090000000-25eb03240c1ec5a1c4462021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 20V, Negative-QTOFsplash10-00e9-2390000000-be3c5228dbf1f7a8f8bb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketocyclophosphamide 40V, Negative-QTOFsplash10-01si-9210000000-7758cd4ad83b31237ca42021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07644
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound33676
PDB IDNot Available
ChEBI ID1887
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available