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Record Information
Version3.6
Creation Date2013-07-04 18:59:43 UTC
Update Date2016-02-11 08:13:00 UTC
HMDB IDHMDB60792
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Thioxanthylic acid
Description6-Thioxanthylic 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
SynonymsNot Available
Chemical FormulaC10H13N4O8PS
Average Molecular Weight380.271
Monoisotopic Molecular Weight380.019170614
IUPAC Name{[(2S,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanyl-9H-purin-9-yl)oxolan-2-yl](hydroxy)methyl}phosphonic acid
Traditional Name[(2S,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanylpurin-9-yl)oxolan-2-yl](hydroxy)methylphosphonic acid
CAS Registry NumberNot Available
SMILES
OC([C@H]1O[C@H](C(O)C1O)N1C=NC2=C1N=C(O)N=C2S)P(O)(O)=O
InChI Identifier
InChI=1/C10H13N4O8PS/c15-3-4(16)8(22-5(3)9(17)23(19,20)21)14-1-11-2-6(14)12-10(18)13-7(2)24/h1,3-5,8-9,15-17H,(H2,19,20,21)(H2,12,13,18,24)/t3?,4?,5-,8+,9?/s2
InChI KeyInChIKey=GRTRLPZIJODDLV-MLERWHMINA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • 6-thiopurine
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Oxolane
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organophosphorus compound
  • Organonitrogen compound
  • Alcohol
  • 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 Solubility3.23 mg/mLALOGPS
logP-0.91ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area191.28 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.84 m3·mol-1ChemAxon
Polarizability31.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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 IDDBMET00771
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 LinkHMDB60792
Metagene LinkHMDB60792
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