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Showing metabocard for 6-Thioguanosine monophosphate (HMDB0060415)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:01:02 UTC
Update Date2017-12-20 20:31:22 UTC
HMDB IDHMDB0060415
Secondary Accession Numbers
  • HMDB60415
Metabolite Identification
Common Name6-Thioguanosine monophosphate
Description6-Thioguanosine 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) Norcodeine
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6-TG NucleotideMeSH
6-Thioguanine nucleotideMeSH
6-Thioguanosine-5'-phosphateMeSH
Chemical FormulaC10H14N5O7PS
Average Molecular Weight379.286
Monoisotopic Molecular Weight379.035155029
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=S)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C10H14N5O7PS/c11-10-13-7-4(8(24)14-10)12-2-15(7)9-6(17)5(16)3(22-9)1-21-23(18,19)20/h2-3,5-6,9,16-17H,1H2,(H2,18,19,20)(H3,11,13,14,24)/t3-,5-,6-,9-/m1/s1
InChI KeyBPZXYEUJBFHASJ-UUOKFMHZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Purinethione
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • 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
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility1.81 g/LALOGPS
logP-1.4ALOGPS
logP-3.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)3.39ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area184.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.05 m³·mol⁻¹ChemAxon
Polarizability33.25 ųChemAxon
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-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9532000000-554f8c59640cc644586eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9311200000-aa4075f5626be7ed4fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0913000000-96a4f72bf492be7f7409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-dfebaa4c8fd99d57db92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-f58433842072d381834eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6519000000-238224e8d8f10e7d2ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9700000000-001e7924823178c2fa60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-37c3f1a5f378f4931d75View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Azathioprine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Mercaptopurine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Mercaptopurine Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Thioguanine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Thioguanine Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
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 IDNot Available
      KEGG Compound IDC16619
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3034646
      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

      Enzyme Details
      1. Thiopurine S-methyltransferase
      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
      Enzyme Details
      2. Hypoxanthine-guanine phosphoribosyltransferase
      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
      Thioguanine + Phosphoribosyl pyrophosphate → 6-Thioguanosine monophosphate + Pyrophosphatedetails
      Enzyme Details
      3. GMP synthase [glutamine-hydrolyzing]
      General function:
      Involved in catalytic activity
      Specific function:
      Involved in the de novo synthesis of guanine nucleotides which are not only essential for DNA and RNA synthesis, but also provide GTP, which is involved in a number of cellular processes important for cell division.
      Gene Name:
      GMPS
      Uniprot ID:
      P49915
      Molecular weight:
      76714.79
      Reactions
      6-Thioxanthine 5'-monophosphate + Adenosine triphosphate + L-Glutamine + Water → 6-Thioguanosine monophosphate + Adenosine monophosphate + Pyrophosphate + L-Glutamic aciddetails