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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:01:16 UTC
Update Date2019-07-23 07:14:17 UTC
HMDB IDHMDB0060418
Secondary Accession Numbers
  • HMDB60418
Metabolite Identification
Common Name6-Thioxanthine 5'-monophosphate
Description6-Thioxanthine 5'-monophosphate, also known as TXMP, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 6-Thioxanthine 5'-monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Mercaptopurine (also called 6-mercaptopurine, 6-MP or its brand name Purinethol) is an immunosuppressive drug. 6-Thioxanthine 5'-monophosphate exists in all living organisms, ranging from bacteria to humans. It is a thiopurine. 6-Thioxanthine 5'-monophosphate is a metabolite of mercaptopurine.
Structure
Data?1563866057
Synonyms
ValueSource
6-Thioxanthine 5'-monophosphoric acidGenerator
TXMPHMDB
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonateGenerator
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulphanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonateGenerator
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulphanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acidGenerator
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
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Vinylogous amide
  • Fluorohydrin
  • Halohydrin
  • Lactam
  • Secondary alcohol
  • Urea
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Alkyl halide
  • Organic nitrogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility2.58 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9523000000-dffd65f6f9b3f395e35cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000t-9212160000-031cbb74e46c2fc16fe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0913000000-adaace6ec0bd7f94e285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-52fd42080cdb25cd93ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3900000000-eb97706814e439831e37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6519000000-94c1850c377ed5317ef3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9500000000-fc4a0474cb0cb72455fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-7b543cc08d4af0099288Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16618
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3081384
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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