thioguanine   Click here for help

GtoPdb Ligand ID: 6845

Synonyms: 6-mercaptoguanine | 6-thioguanine | Lanvis® | Tabloid®
Approved drug PDB Ligand
thioguanine is an approved drug (FDA (1966))
Compound class: Synthetic organic
Comment: Inhibits inosine-5'-monophosphate dehydrogenase 1.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 0
Topological polar surface area 115.47
Molecular weight 167.03
XLogP 0.6
No. Lipinski's rules broken 0
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Canonical SMILES Nc1nc(=S)c2c([nH]1)nc[nH]2
Isomeric SMILES Nc1nc(=S)c2c([nH]1)nc[nH]2
InChI InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
1. Elgemeie GH. (2003)
Thioguanine, mercaptopurine: their analogs and nucleosides as antimetabolites.
Curr Pharm Des, 9 (31): 2627-42. [PMID:14529546]
2. Moreau AC, Paul S, Del Tedesco E, Rinaudo-Gaujous M, Boukhadra N, Genin C, Peyrin-Biroulet L, Roblin X. (2014)
Association between 6-thioguanine nucleotides levels and clinical remission in inflammatory disease: a meta-analysis.
Inflamm Bowel Dis, 20 (3): 464-71. [PMID:24418904]
3. Vethe NT, Bremer S, Bergan S. (2008)
IMP dehydrogenase basal activity in MOLT-4 human leukaemia cells is altered by mycophenolic acid and 6-thioguanosine.
Scand J Clin Lab Invest, 68 (4): 277-85. [PMID:18609073]