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 19:13:49 UTC
Update Date2019-07-23 07:14:52 UTC
HMDB IDHMDB0060690
Secondary Accession Numbers
  • HMDB60690
Metabolite Identification
Common Name4-Ketoifosfamide
Description4-Ketoifosfamide belongs to the class of organic compounds 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. 4-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. 4-Ketoifosfamide is a very weakly acidic compound (based on its pKa). In humans, 4-ketoifosfamide is involved in ifosfamide metabolism pathway. It is sometimes abbreviated 'IFO'.
Structure
Data?1563866092
Synonyms
ValueSource
4-Ketoifosfamide, (S)-isomerHMDB
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
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazaphosphinanes
Sub ClassIsofamides
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
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 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
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]+146.3230932474
DeepCCS[M-H]-143.96230932474
DeepCCS[M-2H]-178.67830932474
DeepCCS[M+Na]+154.01830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-KetoifosfamideClCCNP1(=O)OCCC(=O)N1CCCl2962.2Standard polar33892256
4-KetoifosfamideClCCNP1(=O)OCCC(=O)N1CCCl2043.4Standard non polar33892256
4-KetoifosfamideClCCNP1(=O)OCCC(=O)N1CCCl2175.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Ketoifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl2156.9Semi standard non polar33892256
4-Ketoifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl2126.1Standard non polar33892256
4-Ketoifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl3066.6Standard polar33892256
4-Ketoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl2424.7Semi standard non polar33892256
4-Ketoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl2372.7Standard non polar33892256
4-Ketoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(=O)N1CCCl3196.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ketoifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-4890000000-70b09f3838e2ec71629d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ketoifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ketoifosfamide 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-Ketoifosfamide 10V, Positive-QTOFsplash10-0a4i-9020000000-61b100347818e415b7a82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Positive-QTOFsplash10-001i-9000000000-1913777d6533a9470ec52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Positive-QTOFsplash10-0a4i-9000000000-55575a2a20e4b52707782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Negative-QTOFsplash10-03di-3790000000-65c483ba55dc262acdb72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Negative-QTOFsplash10-001i-8900000000-d416672ac210c11662ec2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Negative-QTOFsplash10-004l-9000000000-bebe75fba33a4f3c36052017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Positive-QTOFsplash10-004i-0190000000-857350524f92bcf3baa72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Positive-QTOFsplash10-004i-1390000000-125e4d12e3fd0e230a4f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Positive-QTOFsplash10-03di-9400000000-b8e82bcd1f6f054915532021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 10V, Negative-QTOFsplash10-00di-0090000000-f86efbbe1892f50c3efc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 20V, Negative-QTOFsplash10-00dl-0960000000-ad8a206b47214fd392752021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ketoifosfamide 40V, Negative-QTOFsplash10-03dr-2900000000-865ce1fbfb062cd90eb42021-10-12Wishart 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 IDC16554
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound99303
PDB IDNot Available
ChEBI ID80561
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