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 Date2013-06-15 17:14:02 UTC
Update Date2019-07-23 07:14:39 UTC
HMDB IDHMDB0060588
Secondary Accession Numbers
  • HMDB60588
Metabolite Identification
Common NameAldoifosfamide
DescriptionAldoifosfamide 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. Aldoifosfamide is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, aldoifosfamide is involved in ifosfamide metabolism pathway. Ifosfamide (pronounced eye. fos'. fa. mide) (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. Aldoifosfamide is a metabolite of ifosfamide. It is sometimes abbreviated 'IFO''.
Structure
Data?1563866079
SynonymsNot Available
Chemical FormulaC7H15Cl2N2O3P
Average Molecular Weight277.085
Monoisotopic Molecular Weight276.019734282
IUPAC Name3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propanal
Traditional Namealdoifosfamide
CAS Registry NumberNot Available
SMILES
ClCCNP(=O)(NCCCl)OCCC=O
InChI Identifier
InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13,11-5-3-9)14-7-1-6-12/h6H,1-5,7H2,(H2,10,11,13)
InChI KeyIPTJZZUYNOWWHM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Phosphoric acid ester
  • Alpha-hydrogen aldehyde
  • Aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic nitrogen 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 Solubility3.58 g/LALOGPS
logP0.23ALOGPS
logP-0.46ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.24ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.43 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.54 m³·mol⁻¹ChemAxon
Polarizability25.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+153.18430932474
DeepCCS[M-H]-149.39630932474
DeepCCS[M-2H]-186.32930932474
DeepCCS[M+Na]+162.01830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AldoifosfamideClCCNP(=O)(NCCCl)OCCC=O2849.3Standard polar33892256
AldoifosfamideClCCNP(=O)(NCCCl)OCCC=O1823.3Standard non polar33892256
AldoifosfamideClCCNP(=O)(NCCCl)OCCC=O2005.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aldoifosfamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl2264.8Semi standard non polar33892256
Aldoifosfamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl2013.6Standard non polar33892256
Aldoifosfamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl3220.4Standard polar33892256
Aldoifosfamide,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O2159.2Semi standard non polar33892256
Aldoifosfamide,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O1973.2Standard non polar33892256
Aldoifosfamide,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O2988.0Standard polar33892256
Aldoifosfamide,2TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2218.8Semi standard non polar33892256
Aldoifosfamide,2TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2127.2Standard non polar33892256
Aldoifosfamide,2TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2771.8Standard polar33892256
Aldoifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C2193.6Semi standard non polar33892256
Aldoifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C2095.7Standard non polar33892256
Aldoifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C2561.1Standard polar33892256
Aldoifosfamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2262.6Semi standard non polar33892256
Aldoifosfamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2223.3Standard non polar33892256
Aldoifosfamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2543.2Standard polar33892256
Aldoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl2484.9Semi standard non polar33892256
Aldoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl2252.0Standard non polar33892256
Aldoifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl3262.6Standard polar33892256
Aldoifosfamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O2423.9Semi standard non polar33892256
Aldoifosfamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O2221.7Standard non polar33892256
Aldoifosfamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O3012.6Standard polar33892256
Aldoifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2671.6Semi standard non polar33892256
Aldoifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2549.7Standard non polar33892256
Aldoifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2860.3Standard polar33892256
Aldoifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C2673.9Semi standard non polar33892256
Aldoifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C2445.5Standard non polar33892256
Aldoifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C2713.7Standard polar33892256
Aldoifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2910.6Semi standard non polar33892256
Aldoifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2713.3Standard non polar33892256
Aldoifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2757.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aldoifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zor-3790000000-6de4991d540fdb25ecad2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aldoifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aldoifosfamide 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 - Aldoifosfamide 10V, Positive-QTOFsplash10-057i-6090000000-1430dc02a1a6d05a0ef72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Positive-QTOFsplash10-0a59-9000000000-22aeb8eca73f0446e9ed2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Positive-QTOFsplash10-08ir-9000000000-0c1e120b60e087bdf7772017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Negative-QTOFsplash10-01t9-3090000000-47f8b09177079f2eff822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Negative-QTOFsplash10-03di-9440000000-3e4b4b1eab5d2716995e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Negative-QTOFsplash10-004i-9100000000-ddd742ec6e60562672f92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Negative-QTOFsplash10-004i-0090000000-dc92791f6cc6d866bc692021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Negative-QTOFsplash10-001r-3930000000-44b28453b068415780e22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Negative-QTOFsplash10-001r-0900000000-84646643ba94403331192021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Positive-QTOFsplash10-004i-1090000000-2e357be8ddb1b4c031432021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Positive-QTOFsplash10-0api-5950000000-1c1676e1bfd7707bc8902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Positive-QTOFsplash10-0a4i-7900000000-60a3e007d394a390a9c12021-10-12Wishart 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 Locations
  • Cytoplasm
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 IDC16556
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound189733
PDB IDNot Available
ChEBI IDNot Available
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