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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:15 UTC
Update Date2023-02-21 17:18:05 UTC
HMDB IDHMDB0013859
Secondary Accession Numbers
  • HMDB13859
Metabolite Identification
Common Name2-Dechloroethylifosfamide
Description2-Dechloroethylifosfamide is a metabolite of the antitumor, alkylating drug Ifosfamide. 2-dechloroethylifosfamide 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. 2-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of cytochrome P450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221 ). 2-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.
Structure
Data?1676999885
Synonyms
ValueSource
2-DClIFHMDB
2-DCE-iffHMDB
2-Amino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazophosphorine-2-O-xideHMDB
Dechloroethylifosfamide, (+-)-isomerHMDB
Dechloroethylifosfamide, (R)-isomerHMDB
Dechloroethylifosfamide, (S)-isomerHMDB
DechloroethylifosfamideHMDB
Chemical FormulaC5H12ClN2O2P
Average Molecular Weight198.588
Monoisotopic Molecular Weight198.032491857
IUPAC Name2-amino-3-(2-chloroethyl)-1,3,2λ⁵-oxazaphosphinan-2-one
Traditional Namedechloroethylifosfamide
CAS Registry Number53459-55-5
SMILES
NP1(=O)OCCCN1CCCl
InChI Identifier
InChI=1S/C5H12ClN2O2P/c6-2-4-8-3-1-5-10-11(8,7)9/h1-5H2,(H2,7,9)
InChI KeyROGLJLJCDSTWBN-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
  • Oxazaphosphinane
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • 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 Solubility46.3 g/LALOGPS
logP-0.36ALOGPS
logP-0.79ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)0.0061ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.24 m³·mol⁻¹ChemAxon
Polarizability17.68 ųChemAxon
Number of Rings1ChemAxon
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]+132.83130932474
DeepCCS[M-H]-130.13830932474
DeepCCS[M-2H]-166.03330932474
DeepCCS[M+Na]+141.22330932474
AllCCS[M+H]+141.332859911
AllCCS[M+H-H2O]+137.232859911
AllCCS[M+NH4]+145.032859911
AllCCS[M+Na]+146.132859911
AllCCS[M-H]-138.132859911
AllCCS[M+Na-2H]-139.832859911
AllCCS[M+HCOO]-141.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-DechloroethylifosfamideNP1(=O)OCCCN1CCCl2327.0Standard polar33892256
2-DechloroethylifosfamideNP1(=O)OCCCN1CCCl1477.7Standard non polar33892256
2-DechloroethylifosfamideNP1(=O)OCCCN1CCCl1736.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Dechloroethylifosfamide,1TMS,isomer #1C[Si](C)(C)NP1(=O)OCCCN1CCCl1719.3Semi standard non polar33892256
2-Dechloroethylifosfamide,1TMS,isomer #1C[Si](C)(C)NP1(=O)OCCCN1CCCl1644.2Standard non polar33892256
2-Dechloroethylifosfamide,1TMS,isomer #1C[Si](C)(C)NP1(=O)OCCCN1CCCl2509.5Standard polar33892256
2-Dechloroethylifosfamide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl1844.7Semi standard non polar33892256
2-Dechloroethylifosfamide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl1845.8Standard non polar33892256
2-Dechloroethylifosfamide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)P1(=O)OCCCN1CCCl2333.6Standard polar33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl1985.6Semi standard non polar33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl1910.9Standard non polar33892256
2-Dechloroethylifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP1(=O)OCCCN1CCCl2686.5Standard polar33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl2262.8Semi standard non polar33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl2284.0Standard non polar33892256
2-Dechloroethylifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P1(=O)OCCCN1CCCl2505.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-5900000000-0197e550072c40b500732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dechloroethylifosfamide 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 - 2-Dechloroethylifosfamide 10V, Positive-QTOFsplash10-0006-9600000000-d7aaece789b967cf6d492016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Positive-QTOFsplash10-01wf-7900000000-5e5fda28174d2f38e0342016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Positive-QTOFsplash10-0006-9100000000-f851ecebf6b0ccd4c5232016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Negative-QTOFsplash10-000i-2900000000-ecfabfb83bc9e1fffb602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Negative-QTOFsplash10-014i-7900000000-8ef68b55534d7b1f386e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Negative-QTOFsplash10-004i-9000000000-14e8ca9900631824076f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Positive-QTOFsplash10-0002-0900000000-30ab82031d48f66f45ce2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Positive-QTOFsplash10-0002-0900000000-4573dc12b33bcf32df762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Positive-QTOFsplash10-03di-9100000000-bd289a1212000ffd9b332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 10V, Negative-QTOFsplash10-0002-0900000000-d67a78722745354ea9442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 20V, Negative-QTOFsplash10-0002-5900000000-baad3afa942ca9d191c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dechloroethylifosfamide 40V, Negative-QTOFsplash10-01t9-9200000000-81ded39078c95bc7eeba2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 ID106420
KEGG Compound IDC16555
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound119105
PDB IDNot Available
ChEBI ID80562
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. Aleksa K, Matsell D, Krausz K, Gelboin H, Ito S, Koren G: Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr Nephrol. 2005 Jul;20(7):872-85. doi: 10.1007/s00467-004-1807-3. Epub 2005 May 4. [PubMed:15875221 ]