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Record Information
Version3.6
Creation Date2013-05-17 01:01:16 UTC
Update Date2016-02-11 08:05:26 UTC
HMDB IDHMDB60418
Secondary Accession NumbersNone
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
SynonymsNot Available
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=1/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-/s2
InChI KeyInChIKey=WMRIOGFRJLQENF-SBTUYZBDNA-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
  • N-glycosyl compound
  • Glycosyl compound
  • 6-thiopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
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 Solubility2.58 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.3 m3·mol-1ChemAxon
Polarizability32.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60418
Metagene LinkHMDB60418
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, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [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