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Record Information
Version3.6
Creation Date2013-06-18 19:13:42 UTC
Update Date2016-02-11 08:11:07 UTC
HMDB IDHMDB60688
Secondary Accession NumbersNone
Metabolite Identification
Common NameNornitrogen mustard
DescriptionNornitrogen mustard is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2,2'-DichlorodiethylamineChEBI
Bis(chloroethyl)amineChEBI
NH-LostChEBI
Chemical FormulaC4H9Cl2N
Average Molecular Weight142.027
Monoisotopic Molecular Weight141.011204707
IUPAC Namebis(2-chloroethyl)amine
Traditional Namebis(2-chloroethyl)amine
CAS Registry NumberNot Available
SMILES
ClCCNCCCl
InChI Identifier
InChI=1S/C4H9Cl2N/c5-1-3-7-4-2-6/h7H,1-4H2
InChI KeyInChIKey=TXFLGZOGNOOEFZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassNitrogen mustard compounds
Sub ClassNot Available
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 Solubility32.2 mg/mLALOGPS
logP1ALOGPS
logP1.14ChemAxon
logS-0.64ALOGPS
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.38 m3·mol-1ChemAxon
Polarizability13.92 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Cyclophosphamide Metabolism PathwaySMP00604Not Available
Cyclophosphamide PathwaySMP00447Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 IDC16552
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60688
Metagene LinkHMDB60688
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID37599
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available