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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:57 UTC
Update Date2019-07-23 07:14:17 UTC
HMDB IDHMDB0060414
Secondary Accession Numbers
  • HMDB0061268
  • HMDB0061339
  • HMDB60414
  • HMDB61268
  • HMDB61339
Metabolite Identification
Common Name6-Methylthiopurine 5'-monophosphate ribonucleotide
Description6-Methylthiopurine 5'-monophosphate ribonucleotide, also known as methylthioinosine-5'-monophosphate or meTIMP, is a metabolite of mercaptopurine. Mercaptopurine (also called 6-mercaptopurine, 6-MP, or its brand name Purinethol) is an immunosuppressive drug. Mercaptopurine is in the thiopurine and antimetabolite family of medications (Wikipedia). MeTIMP produced from 6-thioinosine monophosphate (6-TIMP) by thiopurine methyltransferase (TPMT) is an active metabolite that can inhibit de novo purine biosynthesis. High concentration of meTIMP has been related to hepatotoxicity and myelotoxicity (PMID: 21311411 ).
Structure
Data?1563866057
Synonyms
ValueSource
6-Methylthioinosine-5'-monophosphateKegg
6-Methylthioinosine-5'-monophosphoric acidGenerator
6-Methylthiopurine 5'-monophosphoric acid ribonucleotideGenerator
Methylthioinosine-5'-monophospateHMDB
Methylthioinosine 5'-monophospateGenerator
MeTIMPHMDB
Chemical FormulaC11H15N4O7PS
Average Molecular Weight378.298
Monoisotopic Molecular Weight378.039906056
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolan-2-yl]methoxy}phosphonic acid
Traditional NameMe-TIMP
CAS Registry Number7021-52-5
SMILES
CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H15N4O7PS/c1-24-10-6-9(12-3-13-10)15(4-14-6)11-8(17)7(16)5(22-11)2-21-23(18,19)20/h3-5,7-8,11,16-17H,2H2,1H3,(H2,18,19,20)/t5-,7-,8-,11-/m1/s1
InChI KeyBMYFUCYXRGTQQL-IOSLPCCCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 6-thiopurine
  • Imidazopyrimidine
  • Purine
  • Aryl thioether
  • Alkylarylthioether
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Sulfenyl compound
  • Thioether
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

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 Solubility2.72 g/LALOGPS
logP-2ALOGPS
logP-3.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area160.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.13 m³·mol⁻¹ChemAxon
Polarizability33.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r2-9522000000-aa3c684c39871b1418ebJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9212210000-ac36694e2001bcdf6ffeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0913000000-83e5f1ae357f48429431JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-ccbc23aa8422e91d330bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-ebffe8e04dc10e79a630JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7709000000-e13c15aeacbe8d3e18e9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9700000000-1b85ddeb6a55a46c6703JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-bf54db28750528a4a182JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID8266575
      KEGG Compound IDC16615
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound10091038
      PDB IDNot Available
      ChEBI ID80609
      Food Biomarker OntologyNot Available
      VMH 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 ]
      2. Haglund S, Vikingsson S, Soderman J, Hindorf U, Granno C, Danelius M, Coulthard S, Peterson C, Almer S: The role of inosine-5'-monophosphate dehydrogenase in thiopurine metabolism in patients with inflammatory bowel disease. Ther Drug Monit. 2011 Apr;33(2):200-8. doi: 10.1097/FTD.0b013e31820b42bb. [PubMed:21311411 ]

      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 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
      6-Methylmercaptopurine + Phosphoribosyl pyrophosphate → 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphatedetails