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Record Information
Version3.6
Creation Date2012-09-06 15:00:15 UTC
Update Date2016-02-11 01:27:33 UTC
HMDB IDHMDB13861
Secondary Accession NumbersNone
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-HydroxyifosfamideChEMBL
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 KeyInChIKey=JHUJMHKRHQPBRG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Oxacycle
  • Azacycle
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
Application
  • Pharmaceutical, waste
Cellular locations
  • Extracellular
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.09 m3·mol-1ChemAxon
Polarizability24.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Ifosfamide Metabolism PathwaySMP00605Not Available
Ifosfamide PathwaySMP00448Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry
  • Not Applicable
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
NuGOwiki LinkHMDB13861
Metagene LinkHMDB13861
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available