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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 19:13:56 UTC
Update Date2019-07-23 07:14:52 UTC
HMDB IDHMDB0060692
Secondary Accession Numbers
  • HMDB60692
Metabolite Identification
Common NameCarboxyifosfamide
DescriptionCarboxyifosfamide 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. Carboxyifosfamide is an extremely weak basic (essentially neutral) compound (based on its pKa). carboxyifosfamide can be biosynthesized from aldoifosfamide through the action of the enzyme retinal dehydrogenase 1. In humans, carboxyifosfamide is involved in ifosfamide metabolism pathway. Carboxyifosfamide is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated 'IFO'.
Structure
Data?1563866092
Synonyms
ValueSource
3-({Bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoic acidHMDB
3-({Bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoateHMDB
Chemical FormulaC7H15Cl2N2O4P
Average Molecular Weight293.085
Monoisotopic Molecular Weight292.014648904
IUPAC Name3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
Traditional Namecarboxyifosfamide
CAS Registry NumberNot Available
SMILES
OC(=O)CCOP(=O)(NCCCl)NCCCl
InChI Identifier
InChI=1S/C7H15Cl2N2O4P/c8-2-4-10-16(14,11-5-3-9)15-6-1-7(12)13/h1-6H2,(H,12,13)(H2,10,11,14)
InChI KeyDNDBVHDNSYHKLI-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • 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 Solubility3.76 g/LALOGPS
logP-1.4ALOGPS
logP-0.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area87.66 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity61.47 m³·mol⁻¹ChemAxon
Polarizability26.1 ųChemAxon
Number of Rings0ChemAxon
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]+155.43230932474
DeepCCS[M-H]-153.07430932474
DeepCCS[M-2H]-187.57830932474
DeepCCS[M+Na]+162.23830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarboxyifosfamideOC(=O)CCOP(=O)(NCCCl)NCCCl3475.7Standard polar33892256
CarboxyifosfamideOC(=O)CCOP(=O)(NCCCl)NCCCl2026.5Standard non polar33892256
CarboxyifosfamideOC(=O)CCOP(=O)(NCCCl)NCCCl2228.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carboxyifosfamide,1TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)NCCCl2260.5Semi standard non polar33892256
Carboxyifosfamide,1TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC(=O)O2304.2Semi standard non polar33892256
Carboxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2276.0Semi standard non polar33892256
Carboxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2195.7Standard non polar33892256
Carboxyifosfamide,2TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C2946.9Standard polar33892256
Carboxyifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C2357.4Semi standard non polar33892256
Carboxyifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C2213.9Standard non polar33892256
Carboxyifosfamide,2TMS,isomer #2C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C2899.4Standard polar33892256
Carboxyifosfamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2351.8Semi standard non polar33892256
Carboxyifosfamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2278.5Standard non polar33892256
Carboxyifosfamide,3TMS,isomer #1C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C2651.5Standard polar33892256
Carboxyifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)NCCCl2517.8Semi standard non polar33892256
Carboxyifosfamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC(=O)O2552.8Semi standard non polar33892256
Carboxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2754.2Semi standard non polar33892256
Carboxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C2614.7Standard non polar33892256
Carboxyifosfamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C3041.3Standard polar33892256
Carboxyifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C2820.5Semi standard non polar33892256
Carboxyifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C2570.9Standard non polar33892256
Carboxyifosfamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C3036.6Standard polar33892256
Carboxyifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C3018.5Semi standard non polar33892256
Carboxyifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2766.0Standard non polar33892256
Carboxyifosfamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C2902.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-05tf-1890000000-2eff8b9169eef6666cd32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyifosfamide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5391000000-d216d7335b85567daad52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxyifosfamide 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 - Carboxyifosfamide 10V, Positive-QTOFsplash10-004i-4090000000-ed86043bb226a0a90c732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Positive-QTOFsplash10-0089-9000000000-04cd05b425913ba7aabd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Positive-QTOFsplash10-01t9-9000000000-0e5440da361aec660c7f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Negative-QTOFsplash10-002f-2090000000-4f81c39a66666414545e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Negative-QTOFsplash10-0ik9-9450000000-bfe03fb15784b1311ec52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Negative-QTOFsplash10-004i-9100000000-ddd742ec6e60562672f92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Negative-QTOFsplash10-0006-0090000000-16bff749b532fb94032d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Negative-QTOFsplash10-015i-0940000000-ce35c5ce8b6fb3d9148e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Negative-QTOFsplash10-000l-0900000000-dbed6c8ef07e81daea312021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Positive-QTOFsplash10-0006-0090000000-87d1d71c5b58ac18a93b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Positive-QTOFsplash10-0ac0-3960000000-6d053255e23c8e96819c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Positive-QTOFsplash10-0a4i-5900000000-bf79be778247d8d705b52021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDC16557
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124143
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