You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2013-05-17 01:00:51 UTC
Update Date2017-09-23 14:09:51 UTC
HMDB IDHMDB0060413
Secondary Accession Numbers
  • HMDB60413
Metabolite Identification
Common Name6-Methylthioguanosine monophosphate
Description6-Methylthioguanosine monophosphate is a metabolite of tioguanine. Tioguanine, formerly thioguanine, is a drug that is used in the treatment of cancer. It belongs to the family of drugs called antimetabolites. It is a guanine analog. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H16N5O7PS
Average Molecular Weight393.313
Monoisotopic Molecular Weight393.050805093
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[2-imino-6-(methylsulfanyl)-3,9-dihydro-2H-purin-9-yl]oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-3,4-dihydroxy-5-[2-imino-6-(methylsulfanyl)-3H-purin-9-yl]oxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CSC1=NC(=N)NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H16N5O7PS/c1-25-9-5-8(14-11(12)15-9)16(3-13-5)10-7(18)6(17)4(23-10)2-22-24(19,20)21/h3-4,6-7,10,17-18H,2H2,1H3,(H2,12,14,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1
InChI KeyQJRQZGPABIMRAZ-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
  • 6-thiopurine
  • Imidazopyrimidine
  • Purine
  • Aryl thioether
  • Aminopyrimidine
  • Alkylarylthioether
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Thioether
  • Organosulfur compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 Solubility2.41 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.33ChemAxon
pKa (Strongest Basic)5.57ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area182.51 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.85 m3·mol-1ChemAxon
Polarizability35.11 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
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 ID10562919
      KEGG Compound IDC16620
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060413
      METLIN IDNot Available
      PubChem Compound21820757
      PDB IDNot Available
      ChEBI ID1267083
      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-Thioguanosine monophosphate + S-Adenosylmethionine → 6-Methylthioguanosine monophosphate + S-Adenosylhomocysteinedetails