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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 19:13:53 UTC
Update Date2019-07-23 07:14:52 UTC
HMDB IDHMDB0060691
Secondary Accession Numbers
  • HMDB60691
Metabolite Identification
Common NameIsophosphamide mustard
DescriptionIsophosphamide mustard, also known as palifosfamide-tris or ifosforamide mustard, belongs to the class of organic compounds known as organic phosphoric acid diamides. These are organophosphorus compounds with the general formula RNP(R2)(O)=O (R=alkyl, aryl; R2 = amine group). Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. Isophosphamide mustard is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, isophosphamide mustard is involved in ifosfamide metabolism pathway. Isophosphamide mustard is a metabolite of ifosfamide. It is sometimes abbreviated 'IFO'.
Structure
Data?1563866092
Synonyms
ValueSource
Ifosfamide mustardKegg
NN'-Bis-(2-chloroethyl)phosphoric acidHMDB
Zio-201isophosphamide mustardHMDB
NN'-Bis-(2-chloroethyl)phosphateHMDB
Palifosfamide-trisHMDB
Isophosphoramide mustardHMDB
Ifosforamide mustardHMDB
IPAMHMDB
N,N'-di-(2-chloroethyl)phosphorodiamidic acidHMDB
Iphosphoramide mustardHMDB
Isophosphamide mustardMeSH
PalifosfamideMeSH
Chemical FormulaC4H11Cl2N2O2P
Average Molecular Weight221.022
Monoisotopic Molecular Weight219.993519532
IUPAC Namebis[(2-chloroethyl)amino]phosphinic acid
Traditional NameIPAM
CAS Registry NumberNot Available
SMILES
OP(=O)(NCCCl)NCCCl
InChI Identifier
InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)
InChI KeyBKCJZNIZRWYHBN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphoric acid diamides. These are organophosphorus compounds with the general formula RNP(R2)(O)=O (R=alkyl, aryl; R2 = amine group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoramides
Direct ParentOrganic phosphoric acid diamides
Alternative Parents
Substituents
  • Organic phosphoric acid diamide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility8.86 g/LALOGPS
logP-0.37ALOGPS
logP-0.39ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)5.43ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.2 m³·mol⁻¹ChemAxon
Polarizability19 ųChemAxon
Number of Rings0ChemAxon
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]+144.60430932474
DeepCCS[M-H]-141.69730932474
DeepCCS[M-2H]-177.77430932474
DeepCCS[M+Na]+153.3130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isophosphamide mustardOP(=O)(NCCCl)NCCCl2714.8Standard polar33892256
Isophosphamide mustardOP(=O)(NCCCl)NCCCl1632.2Standard non polar33892256
Isophosphamide mustardOP(=O)(NCCCl)NCCCl1771.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isophosphamide mustard,1TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)NCCCl1845.8Semi standard non polar33892256
Isophosphamide mustard,1TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)NCCCl1636.4Standard non polar33892256
Isophosphamide mustard,1TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)NCCCl2558.1Standard polar33892256
Isophosphamide mustard,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl1890.2Semi standard non polar33892256
Isophosphamide mustard,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl1706.3Standard non polar33892256
Isophosphamide mustard,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)NCCCl2703.0Standard polar33892256
Isophosphamide mustard,2TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C1844.0Semi standard non polar33892256
Isophosphamide mustard,2TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C1797.3Standard non polar33892256
Isophosphamide mustard,2TMS,isomer #1C[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2163.6Standard polar33892256
Isophosphamide mustard,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C1902.5Semi standard non polar33892256
Isophosphamide mustard,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C1876.9Standard non polar33892256
Isophosphamide mustard,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C2307.8Standard polar33892256
Isophosphamide mustard,3TMS,isomer #1C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C1949.8Semi standard non polar33892256
Isophosphamide mustard,3TMS,isomer #1C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C1930.4Standard non polar33892256
Isophosphamide mustard,3TMS,isomer #1C[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2013.8Standard polar33892256
Isophosphamide mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl2092.2Semi standard non polar33892256
Isophosphamide mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl1883.3Standard non polar33892256
Isophosphamide mustard,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)NCCCl2619.5Standard polar33892256
Isophosphamide mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl2147.9Semi standard non polar33892256
Isophosphamide mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl1989.1Standard non polar33892256
Isophosphamide mustard,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)NCCCl2745.5Standard polar33892256
Isophosphamide mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2340.4Semi standard non polar33892256
Isophosphamide mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2225.4Standard non polar33892256
Isophosphamide mustard,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2343.2Standard polar33892256
Isophosphamide mustard,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C2365.8Semi standard non polar33892256
Isophosphamide mustard,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C2300.4Standard non polar33892256
Isophosphamide mustard,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(O)N(CCCl)[Si](C)(C)C(C)(C)C2481.6Standard polar33892256
Isophosphamide mustard,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2586.6Semi standard non polar33892256
Isophosphamide mustard,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2456.9Standard non polar33892256
Isophosphamide mustard,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2332.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isophosphamide mustard GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g3-6910000000-53a3ebd8119a9d7c12be2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isophosphamide mustard 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 - Isophosphamide mustard 10V, Positive-QTOFsplash10-00e9-6090000000-28910cc262fc920160d62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Positive-QTOFsplash10-03ec-9300000000-53d6095d0fd353a7d7e92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Positive-QTOFsplash10-03di-9000000000-7cab03f69a1bc707e1a92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Negative-QTOFsplash10-066r-5890000000-e9d8316ea01b6f710a852017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Negative-QTOFsplash10-03di-9220000000-866eaf3137df6ba4df532017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Negative-QTOFsplash10-004l-9000000000-399fa980332aaff6d2592017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Positive-QTOFsplash10-0006-0900000000-648a2ec89fc0f64efb3b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Positive-QTOFsplash10-01po-7900000000-967a41020240370616d42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Positive-QTOFsplash10-03di-9000000000-f1751c47be60b7d124c92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 10V, Negative-QTOFsplash10-014i-0090000000-0e92f2f71d4e7fd828402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 20V, Negative-QTOFsplash10-004i-9210000000-021eb4b0e46c0edb4d812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isophosphamide mustard 40V, Negative-QTOFsplash10-004i-9000000000-44e5373925906348e0412021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H 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 IDC16559
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100427
PDB IDNot Available
ChEBI ID80566
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