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Record Information
Version3.6
Creation Date2013-06-18 17:47:59 UTC
Update Date2016-02-11 08:10:25 UTC
HMDB IDHMDB60659
Secondary Accession NumbersNone
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 KeyInChIKey=HSCOLDQJZRZQMV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentNitroimidazoles
Alternative Parents
Substituents
  • Nitroimidazole
  • Imidolactam
  • N-substituted imidazole
  • Heteroaromatic compound
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility3.14 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.55 m3·mol-1ChemAxon
Polarizability11.09 Å3ChemAxon
Number of Rings1ChemAxon
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
Azathioprine Metabolism PathwaySMP00645Not Available
Azathioprine PathwaySMP00427Not 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 IDC16621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60659
Metagene LinkHMDB60659
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