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Record Information
Version3.6
Creation Date2013-07-09 16:16:24 UTC
Update Date2016-02-11 08:17:57 UTC
HMDB IDHMDB61068
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-methylazathioprine
DescriptionS-methylazathioprine 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 FormulaC10H10N7O2S
Average Molecular Weight292.297
Monoisotopic Molecular Weight292.061668289
IUPAC Namemethyl(1-methyl-4-nitro-1H-imidazol-5-yl)9H-purin-6-ylsulfanium
Traditional Namemethyl(3-methyl-5-nitroimidazol-4-yl)9H-purin-6-ylsulfanium
CAS Registry NumberNot Available
SMILES
CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O
InChI Identifier
InChI=1/C10H10N7O2S/c1-16-5-15-8(17(18)19)10(16)20(2)9-6-7(12-3-11-6)13-4-14-9/h3-5H,1-2H3,(H,11,12,13,14)/q+1
InChI KeyInChIKey=CAGKKYGOGIIIDP-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Nitroimidazole
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Azacycle
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organosulfur compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.23 mg/mLALOGPS
logP1.47ALOGPS
logP-0.33ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.1 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.84 m3·mol-1ChemAxon
Polarizability26.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot 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 IDDBMET00416
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
NuGOwiki LinkHMDB61068
Metagene LinkHMDB61068
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available