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Record Information
Version3.6
Creation Date2013-05-17 01:00:51 UTC
Update Date2016-02-11 08:05:20 UTC
HMDB IDHMDB60413
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=QJRQZGPABIMRAZ-YPLCUDRINA-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
  • Alkylarylthioether
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • 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 Solubility2.41 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
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 ID10562919
KEGG Compound IDC16620
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60413
Metagene LinkHMDB60413
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, 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 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