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Record Information
Version4.0
Creation Date2013-05-17 01:01:16 UTC
Update Date2017-09-27 08:43:46 UTC
HMDB IDHMDB0060418
Secondary Accession Numbers
  • HMDB60418
Metabolite Identification
Common Name6-Thioxanthine 5'-monophosphate
Description6-Thioxanthine 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
TXMPMeSH
Chemical FormulaC10H13N4O8PS
Average Molecular Weight380.271
Monoisotopic Molecular Weight380.019170614
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional NameTXMP
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2S
InChI Identifier
InChI=1S/C10H13N4O8PS/c15-5-3(1-21-23(18,19)20)22-9(6(5)16)14-2-11-4-7(14)12-10(17)13-8(4)24/h2-3,5-6,9,15-16H,1H2,(H2,18,19,20)(H2,12,13,17,24)/t3-,5-,6-,9-/m1/s1
InChI KeyWMRIOGFRJLQENF-UUOKFMHZSA-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
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidinethione
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Thiolactam
  • Imidazole
  • Secondary alcohol
  • Urea
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

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 Solubility2.58 g/LALOGPS
logP-0.59ALOGPS
logP-1.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)0.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area180.28 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.3 m³·mol⁻¹ChemAxon
Polarizability32.57 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-9523000000-dffd65f6f9b3f395e35cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000t-9212160000-031cbb74e46c2fc16fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0913000000-adaace6ec0bd7f94e285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-52fd42080cdb25cd93ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3900000000-eb97706814e439831e37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6519000000-94c1850c377ed5317ef3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9500000000-fc4a0474cb0cb72455fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-7b543cc08d4af0099288View in MoNA
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 ID2339000
      KEGG Compound IDC16618
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3081384
      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 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
      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