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Record Information
Version4.0
Creation Date2013-05-17 01:00:57 UTC
Update Date2017-09-23 14:09:54 UTC
HMDB IDHMDB0060414
Secondary Accession Numbers
  • HMDB60414
StatusExpected but not Quantified
Metabolite Identification
Common Name6-Methylthiopurine 5'-monophosphate ribonucleotide
Description6-Methylthiopurine 5'-monophosphate ribonucleotide 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-Methylthioinosine-5'-monophosphateKegg
6-Methylthioinosine-5'-monophosphoric acidGenerator
6-Methylthiopurine 5'-monophosphoric acid ribonucleotideGenerator
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 NumberNot Available
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
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
  • 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
Process
Naturally occurring process:
Biological process:
Biochemical pathway:
Disposition
Biological Location:
Source:
Biofluid and excreta:
Organ and components:
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.13 m3·mol-1ChemAxon
Polarizability33.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Azathioprine PathwayPw000266Pw000266 greyscalePw000266 simpleNot Available
Mercaptopurine Metabolism PathwayPw000585Pw000585 greyscalePw000585 simpleNot Available
Mercaptopurine PathwayPw000267Pw000267 greyscalePw000267 simpleNot Available
Thioguanine PathwayPw000429Pw000429 greyscalePw000429 simpleNot Available
Displaying all 4 entries
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 ID8266575
      KEGG Compound IDC16615
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060414
      METLIN IDNot Available
      PubChem Compound10091038
      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 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