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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:15 UTC
Update Date2021-09-14 15:20:33 UTC
HMDB IDHMDB0013861
Secondary Accession Numbers
  • HMDB13861
Metabolite Identification
Common Name4-Hydroxyifosfamide
Description4-Hydroxyifosfamide is the active metabolite of the bifunctional alkylating cytostatic drug known as ifosfamide. 4-Hydroxyifosfamide is a member of the compound class known as oxazaphosphorines. Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. 4-Hydroxyifosfamide is very unstable in plasma and a stabilization procedure by adding citric acid has been developed (PMID: 9172103 ). 4-Hydroxyifosfamide is known to pass through the blood-brain barrier, and can reach cerebrospinal fluid concentrations that are almost as high as plasma concentrations (PMID: 9677448 ). 4-Hydroxyifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.
Structure
Data?1582753149
Synonyms
ValueSource
4-Hydroxy-ifosfamideHMDB
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinan-4-ol 2-oxideHMDB
Chemical FormulaC7H15Cl2N2O3P
Average Molecular Weight277.085
Monoisotopic Molecular Weight276.019734282
IUPAC Name3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one
Traditional Name4-hydroxyifosfamide
CAS Registry Number67292-64-2
SMILES
OC1CCOP(=O)(NCCCl)N1CCCl
InChI Identifier
InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)
InChI KeyJHUJMHKRHQPBRG-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
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Organic phosphoric acid amide
  • Alkanolamine
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Alkyl chloride
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
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 Solubility22.2 g/LALOGPS
logP-0.06ALOGPS
logP-0.057ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.91ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.8 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.09 m³·mol⁻¹ChemAxon
Polarizability24.72 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]+148.18930932474
DeepCCS[M-H]-145.81530932474
DeepCCS[M-2H]-181.12130932474
DeepCCS[M+Na]+155.92830932474
AllCCS[M+H]+155.832859911
AllCCS[M+H-H2O]+152.532859911
AllCCS[M+NH4]+158.932859911
AllCCS[M+Na]+159.832859911
AllCCS[M-H]-152.932859911
AllCCS[M+Na-2H]-153.932859911
AllCCS[M+HCOO]-155.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyifosfamideOC1CCOP(=O)(NCCCl)N1CCCl3048.3Standard polar33892256
4-HydroxyifosfamideOC1CCOP(=O)(NCCCl)N1CCCl2062.8Standard non polar33892256
4-HydroxyifosfamideOC1CCOP(=O)(NCCCl)N1CCCl2161.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyifosfamide,1TMS,isomer #1C[Si](C)(C)OC1CCOP(=O)(NCCCl)N1CCCl2142.8Semi standard non polar33892256
4-Hydroxyifosfamide,1TMS,isomer #2C[Si](C)(C)N(CCCl)P1(=O)OCCC(O)N1CCCl2181.4Semi standard non polar33892256
4-Hydroxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl2182.6Semi standard non polar33892256
4-Hydroxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl2132.1Standard non polar33892256
4-Hydroxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl2810.3Standard polar33892256
4-Hydroxyifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCOP(=O)(NCCCl)N1CCCl2367.0Semi standard non polar33892256
4-Hydroxyifosfamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(O)N1CCCl2442.1Semi standard non polar33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl2615.4Semi standard non polar33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl2549.9Standard non polar33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl2965.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-4490000000-68b33a81b7ed610421692017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyifosfamide GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9477000000-c358b806368970e28e8a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyifosfamide 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-Hydroxyifosfamide 10V, Positive-QTOFsplash10-0a4i-9030000000-125f3622a612b6133e452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Positive-QTOFsplash10-001i-9100000000-2dc6532567c6dd55b1702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Positive-QTOFsplash10-0a4l-9000000000-ba299292144772f345bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Negative-QTOFsplash10-03fr-2790000000-5f30604369be13b4f4b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Negative-QTOFsplash10-0089-8900000000-4377372163ecc070ea4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Negative-QTOFsplash10-002f-9000000000-1212b3cc3fd363e6eef82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Negative-QTOFsplash10-004i-0090000000-6c1af332aad878673a4b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Negative-QTOFsplash10-004i-0290000000-939a59c6fbceef5cc6af2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Negative-QTOFsplash10-00bi-3910000000-478bad8cbcb2e8e42d362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Positive-QTOFsplash10-004i-0090000000-368a494088668b022c362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Positive-QTOFsplash10-004i-2390000000-2745c533925b00075ccd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Positive-QTOFsplash10-03di-9300000000-1dd7c346907cc962b5f52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 ID272429
KEGG Compound IDC16553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound308171
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 References
  1. Kaijser GP, Ter Riet PG, de Kraker J, Bult A, Beijnen JH, Underberg WJ: Determination of 4-hydroxyifosfamide in biological matrices by high-performance liquid chromatography. J Pharm Biomed Anal. 1997 Mar;15(6):773-81. doi: 10.1016/s0731-7085(96)01893-6. [PubMed:9172103 ]
  2. Kaijser GP, De Kraker J, Bult A, Underberg WJ, Beijnen JH: Pharmacokinetics of ifosfamide and some metabolites in children. Anticancer Res. 1998 May-Jun;18(3B):1941-9. [PubMed:9677448 ]