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Record Information
Version4.0
Creation Date2012-09-06 15:00:15 UTC
Update Date2017-10-23 19:06:13 UTC
HMDB IDHMDB0013861
Secondary Accession Numbers
  • HMDB13861
Metabolite Identification
Common Name4-Hydroxyifosfamide
Description4-Hydroxyifosfamide is a metabolite of Ifosfamide. 4-hydroxyifosfamide belongs to the family of Anilides. These are organic compounds derived from oxoacids RkE(=O)l(OH)m by replacing an OH group by the NHPh group or derivative formed by ring substitution[1].
Structure
Thumb
Synonyms
ValueSource
4-Hydroxy-ifosfamideMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassOxazaphosphinanes
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-4490000000-68b33a81b7ed61042169View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9477000000-c358b806368970e28e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9030000000-125f3622a612b6133e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-2dc6532567c6dd55b170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-ba299292144772f345bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-2790000000-5f30604369be13b4f4b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-8900000000-4377372163ecc070ea4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-1212b3cc3fd363e6eef8View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Ifosfamide Metabolism PathwayPw000581Pw000581 greyscalePw000581 simpleNot Available
Ifosfamide PathwayPw000249Pw000249 greyscalePw000249 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00024
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound0
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available