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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:20:31 UTC
Update Date2019-07-23 07:14:19 UTC
HMDB IDHMDB0060433
Secondary Accession Numbers
  • HMDB60433
Metabolite Identification
Common NameAldophosphamide
DescriptionDetoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. Detoxification of aldophosphamide may also be effected by enzymes, viz. Thus, NAD-linked oxidation and NADPH-linked reduction of aldophosphamide catalyzed by relevant erythrocyte enzymes were quantified. (PMID: 9394035 ) Class 1 aldehyde dehydrogenases (ALDH-1) function as drug resistance gene products by catalyzing the irreversible conversion of aldophosphamide, an active metabolite of cyclophosphamide, to an inert compound. (PMID: 9322086 )
Structure
Data?1563866059
Synonyms
ValueSource
Cyclophosphamide-mustardHMDB
Cyp-mustardHMDB
Chemical FormulaC7H15Cl2N2O3P
Average Molecular Weight277.085
Monoisotopic Molecular Weight276.019734282
IUPAC Name3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanal
Traditional Namealdophosphamide
CAS Registry NumberNot Available
SMILES
NP(=O)(OCCC=O)N(CCCl)CCCl
InChI Identifier
InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h6H,1-5,7H2,(H2,10,13)
InChI KeyQMGUSPDJTPDFSF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Organic phosphoric acid amide
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aldehyde
  • Alkyl halide
  • Alkyl chloride
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility13.6 g/LALOGPS
logP10(0.55) g/LALOGPS
logP10(-0.46) g/LChemAxon
logS10(-1.3) g/LALOGPS
pKa (Strongest Acidic)13.08ChemAxon
pKa (Strongest Basic)-0.069ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.63 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity60.54 m³·mol⁻¹ChemAxon
Polarizability24.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AldophosphamideNP(=O)(OCCC=O)N(CCCl)CCCl2653.0Standard polar33892256
AldophosphamideNP(=O)(OCCC=O)N(CCCl)CCCl1799.0Standard non polar33892256
AldophosphamideNP(=O)(OCCC=O)N(CCCl)CCCl2013.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aldophosphamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl2199.4Semi standard non polar33892256
Aldophosphamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl2021.2Standard non polar33892256
Aldophosphamide,1TMS,isomer #1C[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl3924.0Standard polar33892256
Aldophosphamide,1TMS,isomer #2C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl2130.8Semi standard non polar33892256
Aldophosphamide,1TMS,isomer #2C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl1997.8Standard non polar33892256
Aldophosphamide,1TMS,isomer #2C[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl2886.3Standard polar33892256
Aldophosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl2204.1Semi standard non polar33892256
Aldophosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl2162.5Standard non polar33892256
Aldophosphamide,2TMS,isomer #1C[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C)N(CCCl)CCCl2708.3Standard polar33892256
Aldophosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2239.6Semi standard non polar33892256
Aldophosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2189.2Standard non polar33892256
Aldophosphamide,2TMS,isomer #2C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2630.1Standard polar33892256
Aldophosphamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2309.4Semi standard non polar33892256
Aldophosphamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2316.9Standard non polar33892256
Aldophosphamide,3TMS,isomer #1C[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C2581.1Standard polar33892256
Aldophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl2421.1Semi standard non polar33892256
Aldophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl2264.2Standard non polar33892256
Aldophosphamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(N)(=O)N(CCCl)CCCl4043.7Standard polar33892256
Aldophosphamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl2398.8Semi standard non polar33892256
Aldophosphamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl2244.8Standard non polar33892256
Aldophosphamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NP(=O)(OCCC=O)N(CCCl)CCCl2930.9Standard polar33892256
Aldophosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl2640.7Semi standard non polar33892256
Aldophosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl2571.4Standard non polar33892256
Aldophosphamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NP(=O)(OCC=CO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl2842.4Standard polar33892256
Aldophosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2695.1Semi standard non polar33892256
Aldophosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2541.9Standard non polar33892256
Aldophosphamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC=O)N(CCCl)CCCl2713.4Standard polar33892256
Aldophosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2940.2Semi standard non polar33892256
Aldophosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2806.2Standard non polar33892256
Aldophosphamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2740.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aldophosphamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r6-3930000000-ff6f36c8b422958020402017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aldophosphamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aldophosphamide 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 - Aldophosphamide 10V, Positive-QTOFsplash10-0a6r-3190000000-ab09c0d99d6be04947212016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 20V, Positive-QTOFsplash10-0a4i-9100000000-4f52a98720e48a89bf672016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 40V, Positive-QTOFsplash10-0bvl-9300000000-b456c4d19d6e29b11aa42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 10V, Negative-QTOFsplash10-03di-1390000000-f2cfbeebb17c18444fc42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 20V, Negative-QTOFsplash10-03xr-9330000000-e296d1c2deb7425c67d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 40V, Negative-QTOFsplash10-0udu-2910000000-ab68ba84f4c31e2560ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 10V, Positive-QTOFsplash10-004i-0390000000-85648cd89df23d1474682021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 20V, Positive-QTOFsplash10-00dl-0790000000-9db4ba9eb9886927554f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 40V, Positive-QTOFsplash10-0btc-9100000000-d3145b5a45da485149012021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 10V, Negative-QTOFsplash10-004i-0090000000-6cd6113372d1d0808e1d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 20V, Negative-QTOFsplash10-0059-2390000000-09ec42c4941802f6cb3d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aldophosphamide 40V, Negative-QTOFsplash10-0pyi-4910000000-eb2eb8022150d34149a42021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDC07645
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclophosphamide
METLIN IDNot Available
PubChem Compound107744
PDB IDNot Available
ChEBI ID2560
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Dockham PA, Sreerama L, Sladek NE: Relative contribution of human erythrocyte aldehyde dehydrogenase to the systemic detoxification of the oxazaphosphorines. Drug Metab Dispos. 1997 Dec;25(12):1436-41. [PubMed:9394035 ]
  3. Bunting KD, Townsend AJ: De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. Elevated class 1 ALDH activity is closely correlated with reduction in DNA interstrand cross-linking and lethality. J Biol Chem. 1996 May 17;271(20):11884-90. [PubMed:8662658 ]
  4. Bunting KD, Webb M, Giorgianni F, Galipeau J, Blakley RL, Townsend AJ, Sorrentino BP: Coding region-specific destabilization of mRNA transcripts attenuates expression from retroviral vectors containing class 1 aldehyde dehydrogenase cDNAs. Hum Gene Ther. 1997 Sep 1;8(13):1531-43. [PubMed:9322086 ]

Only showing the first 10 proteins. There are 30 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Iondetails
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails

Only showing the first 10 proteins. There are 30 proteins in total.