You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2013-05-17 01:20:27 UTC
Update Date2017-09-27 08:43:47 UTC
HMDB IDHMDB0060432
Secondary Accession Numbers
  • HMDB60432
Metabolite Identification
Common NameAlcophosphamide
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 ) It has already been demonstrated that horse liver alcohol dehydrogenase catalyzes the reduction of aldophosphamide to alcophosphamide. (PMID: 8216347 )
Structure
Thumb
SynonymsNot Available
Chemical FormulaC7H17Cl2N2O3P
Average Molecular Weight279.101
Monoisotopic Molecular Weight278.035384346
IUPAC Name3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propan-1-ol
Traditional Namealcophosphamide
CAS Registry NumberNot Available
SMILES
NP(=O)(OCCCO)N(CCCl)CCCl
InChI Identifier
InChI=1S/C7H17Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h12H,1-7H2,(H2,10,13)
InChI KeyBZGFIGVSVQRQBJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Organic phosphoric acid amide
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organochloride
  • Alcohol
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl halide
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility18.8 g/LALOGPS
logP0.3ALOGPS
logP-0.65ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-0.068ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.79 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity61.84 m³·mol⁻¹ChemAxon
Polarizability25.78 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-01r6-4940000000-44137bb9687171ae5e54View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-6590000000-496c0522af4655a53491View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-2090000000-b940569200b9a7c02bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9100000000-3a2c5dc0e1431a7c053bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9300000000-f8dea9ffabf8fb46f226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0490000000-70efe216a63fd9566444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j4i-9240000000-82aeb95e51da24c19738View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udu-2910000000-e03eb5db4480b26b8da8View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID80559
      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. Parekh HK, Sladek NE: NADPH-dependent enzyme-catalyzed reduction of aldophosphamide, the pivotal metabolite of cyclophosphamide. Biochem Pharmacol. 1993 Sep 14;46(6):1043-52. [PubMed:8216347 ]

      Enzymes

      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 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
      General function:
      Involved in zinc ion binding
      Specific function:
      Not Available
      Gene Name:
      ADH1C
      Uniprot ID:
      P00326
      Molecular weight:
      39867.27
      Reactions
      Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NADdetails