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Record Information
Version3.6
Creation Date2013-05-17 01:01:07 UTC
Update Date2017-03-02 22:05:03 UTC
HMDB IDHMDB60416
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Thioinosine-5'-monophosphate
Description6-Thioinosine-5'-monophosphate 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
9-(5-phospho-1-Ribofuranosyl)-6-mercaptopurineKegg
6-Thioinosine-5'-monophosphoric acidGenerator
6-TIMPMeSH
6-Mercaptopurine ribonucleoside 5'-monophosphateMeSH
6-thio-IMPMeSH
6-Thioinosine 5'-monophosphateMeSH
Ion(-2) OF thioinosinic acidMeSH
Chemical FormulaC10H13N4O7PS
Average Molecular Weight364.272
Monoisotopic Molecular Weight364.024255992
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional NameThio-IMP
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2S
InChI Identifier
InChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
InChI KeyZKRFOXLVOKTUTA-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purinethione
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidinethione
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility2.12 mg/mLALOGPS
logP-0.94ALOGPS
logP-1.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)0.45ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.05 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.38 m3·mol-1ChemAxon
Polarizability31.52 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 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 IDDBMET00657
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID2298861
      KEGG Compound IDC04646
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60416
      Metagene LinkHMDB60416
      METLIN IDNot Available
      PubChem Compound3034391
      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 thiopurine S-methyltransferase activity
      Specific function:
      Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
      Gene Name:
      TPMT
      Uniprot ID:
      P51580
      Molecular weight:
      28180.09
      Reactions
      6-Thioinosine-5'-monophosphate + S-Adenosylmethionine → 6-Methylthiopurine 5'-monophosphate ribonucleotide + S-Adenosylhomocysteinedetails
      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
      General function:
      Involved in hypoxanthine phosphoribosyltransferase activity
      Specific function:
      Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
      Gene Name:
      HPRT1
      Uniprot ID:
      P00492
      Molecular weight:
      24579.155
      Reactions
      Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
      General function:
      Involved in catalytic activity
      Specific function:
      Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
      Gene Name:
      IMPDH2
      Uniprot ID:
      P12268
      Molecular weight:
      55804.495
      Reactions
      6-Thioinosine-5'-monophosphate + NAD + Water → 6-Thioxanthine 5'-monophosphate + NADH + Hydrogen Iondetails
      General function:
      Involved in catalytic activity
      Specific function:
      Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
      Gene Name:
      IMPDH1
      Uniprot ID:
      P20839
      Molecular weight:
      63252.24
      Reactions
      6-Thioinosine-5'-monophosphate + NAD + Water → 6-Thioxanthine 5'-monophosphate + NADH + Hydrogen Iondetails