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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:43 UTC
Update Date2017-12-07 16:54:55 UTC
HMDB IDHMDB0060411
Secondary Accession Numbers
  • HMDB60411
Metabolite Identification
Common Name6-Mercaptopurine ribonucleoside triphosphate
Description6-Mercaptopurine ribonucleoside triphosphate is a metabolite of mercaptopurine. Mercaptopurine (also called 6-mercaptopurine, 6-MP or its brand name Purinethol) is an immunosuppressive drug. It is a thiopurine. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
6-Thioinosine-5'-triphosphateKegg
6-Thioinosine-5'-triphosphoric acidGenerator
6-Mercaptopurine ribonucleoside triphosphoric acidGenerator
6-Thioadenosine-5'-triphosphateMeSH
SRTPMeSH
6-mercapto-9 beta-Ribofuranosylpurine-5'-triphosphateMeSH
Chemical FormulaC10H15N4O13P3S
Average Molecular Weight524.231
Monoisotopic Molecular Weight523.956916812
IUPAC Name({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name6-thioinosine-5'-triphosphate
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2S
InChI Identifier
InChI=1S/C10H15N4O13P3S/c15-6-4(1-24-29(20,21)27-30(22,23)26-28(17,18)19)25-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)31/h2-4,6-7,10,15-16H,1H2,(H,20,21)(H,22,23)(H,11,12,31)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
InChI KeyGQNRDWAOABGWGP-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Purinethione
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidinethione
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
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 Solubility3.87 g/LALOGPS
logP-0.25ALOGPS
logP-2.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)0.37ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area253.11 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.12 m³·mol⁻¹ChemAxon
Polarizability40.8 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0a6s-9756120000-b41afea0de6ee35d5555View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0zfs-9453046000-193b206840032795c236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910220000-666e1ef88f40bb3de3a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-bf9fddc007dc6a2c755eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3900000000-7c57fc83b106672f5c2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0820290000-7be13016a045ec78fb71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-7920000000-270b61a833b021d398b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-4ed0dc22f0dd4a21a55eView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 ID2300827
      KEGG Compound IDC16617
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3036942
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Involved in hydrolase activity
      Specific function:
      Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
      Gene Name:
      ITPA
      Uniprot ID:
      Q9BY32
      Molecular weight:
      16833.23
      Reactions
      6-Mercaptopurine ribonucleoside triphosphate + Water → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails