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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:47:59 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060659
Secondary Accession Numbers
  • HMDB60659
Metabolite Identification
Common Name1-Methyl-4-nitroimidazole
Description1-Methyl-4-nitroimidazole is a metabolite of azathioprine. Azathioprine is a purine analogue immunosuppressive drug. It is used to prevent rejection following organ transplantation, and to treat a vast array of autoimmune diseases, including rheumatoid arthritis, pemphigus, inflammatory bowel disease, multiple sclerosis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica or Devic's disease, restrictive lung disease, and others. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC4H5N3O2
Average Molecular Weight127.1014
Monoisotopic Molecular Weight127.038176419
IUPAC Name1-methyl-4-nitro-1H-imidazole
Traditional Name1-methyl-4-nitroimidazole
CAS Registry NumberNot Available
SMILES
CN1C=NC(=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C4H5N3O2/c1-6-2-4(5-3-6)7(8)9/h2-3H,1H3
InChI KeyHSCOLDQJZRZQMV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
Direct ParentNitroimidazoles
Alternative Parents
Substituents
  • Nitroaromatic compound
  • Nitroimidazole
  • N-substituted imidazole
  • Imidolactam
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility3.14 g/LALOGPS
logP-0.23ALOGPS
logP0.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.64 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.55 m³·mol⁻¹ChemAxon
Polarizability11.09 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-004i-9500000000-5572508a2c2c51823d13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-d877350c3caef4c84344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-4900000000-c8ce22a6a8141005a467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9100000000-40b7719a2cb99667331dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-bf396a90d19c67b3089aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-088fbb049b50fa302286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ul1-9000000000-6cc95eb36814b01901d4View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Azathioprine Metabolism PathwayPw000621Pw000621 greyscalePw000621 simpleNot Available
Azathioprine PathwayPw000266Pw000266 greyscalePw000266 simpleNot Available
Displaying all 2 entries
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 IDC16621
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound18209
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available