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Record Information
Version3.6
Creation Date2013-06-15 17:46:44 UTC
Update Date2016-02-11 08:09:06 UTC
HMDB IDHMDB60601
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-thiouric acid
Description6-thiouric acid 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
Synonyms
ValueSource
6-Thiouric acidKegg
6-ThioateGenerator
6-Thioic acidGenerator
6-thio- (Van) (8ci) urateGenerator
Chemical FormulaC5H4N4O2S
Average Molecular Weight184.176
Monoisotopic Molecular Weight184.005496082
IUPAC Name6-sulfanyl-9H-purine-2,8-diol
Traditional Name6-thio- (van) (8CI) uric acid
CAS Registry NumberNot Available
SMILES
O=C1NC2=C(N1)C(=S)NC(=O)N2
InChI Identifier
InChI=1S/C5H4N4O2S/c10-4-6-1-2(7-4)8-5(11)9-3(1)12/h(H4,6,7,8,9,10,11,12)
InChI KeyInChIKey=SXHQUGJSTGOXMD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinones
Alternative Parents
Substituents
  • Purinone
  • Purinethione
  • Pyrimidone
  • Pyrimidinethione
  • Pyrimidine
  • Heteroaromatic compound
  • Thiolactam
  • Imidazole
  • Azole
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility0.91 mg/mLALOGPS
logP0.96ALOGPS
logP1.15ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.92 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.29 m3·mol-1ChemAxon
Polarizability16.25 Å3ChemAxon
Number of Rings2ChemAxon
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
Pathways
NameSMPDB LinkKEGG Link
Azathioprine PathwaySMP00427Not Available
Mercaptopurine Metabolism PathwaySMP00609Not Available
Mercaptopurine PathwaySMP00428Not Available
Thioguanine PathwaySMP00430Not 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 IDDBMET01009
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16613
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60601
Metagene LinkHMDB60601
METLIN IDNot Available
PubChem Compound3032417
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available