THIOGUANINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
UNII WIX31ZPX66
EPA CompTox DTXSID6023652

Structure

InChI Key WYWHKKSPHMUBEB-UHFFFAOYSA-N
Smiles Nc1nc2[nH]cnc2c(=S)[nH]1
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C5H5N5S
Molecular Weight 167.2
AlogP 0.6
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 0.0
Polar Surface Area 83.38
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 11.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR FDA
Protein: Inosine-5'-monophosphate dehydrogenase (IMPDH)
Description: Inosine-5'-monophosphate dehydrogenase 2
Organism : Homo sapiens
P12268 ENSG00000178035
Protein: Inosine-5'-monophosphate dehydrogenase (IMPDH)
Description: Inosine-5'-monophosphate dehydrogenase 1
Organism : Homo sapiens
P20839 ENSG00000106348
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase PAKA subfamily
- - - - 31
Enzyme Oxidoreductase
- 92420 - - -
Enzyme Transferase
- - 18000 - 51
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - - 2
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 108
Assay Description Organism Bioactivity Reference
Inhibition of PAK1 at 31 uM None 31.0 %
Antiproliferative activity against mouse P388 cells after 48 hrs by MTT assay Mus musculus 300.0 nM
Cytotoxicity against human CCRF-CEM cells after 48 hrs by cell titer-blue assay Homo sapiens 870.1 nM
Cytotoxicity against human CCRF-CEM/C2 cells after 48 hrs by cell titer-blue assay Homo sapiens 941.6 nM
PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP region in Salmonella typhi identified in the primary screen. (Class of assay: confirmatory) [Related pubchem assays: 1850, 1864, 1985 ] None 320.0 nM
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 601.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 108.66 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 107.95 %
Antagonist activity at human recombinant dopamine D2 long receptor expressed in CHOK1 cells coexpressing mitochondrial apoaequorin assessed as inhibition of agonist-induced effect at 50 uM after 15 mins by luminometric analysis relative to haloperidol Homo sapiens 21.0 %
Antagonist activity at human recombinant dopamine D1 receptor expressed in CHOK1 cells assessed as inhibition of agonist-induced cAMP accumulation at 100 uM preincubated for 10 mins prior to agonist addition measured after 30 mins by HTRF assay relative to SCH23390 Homo sapiens 2.3 %
Inhibition of GST-tagged Escherichia coli HPPK expressed in Escherichia coli using 6-hydroxymethyl-7,8-dihydropterin hydrochloride as substrate at 250 uM after 20 mins by luminescence assay Escherichia coli 51.0 %
PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 402.37 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 343.1 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 138.55 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 622.4 nM
PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 372.99 nM
PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 49.27 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 108.05 nM
PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 163.26 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 99.92 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 75.02 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 %

Related Entries

Cross References

Resources Reference
ChEBI 9555
ChEMBL CHEMBL727
DrugBank DB00352
DrugCentral 2632
FDA SRS WIX31ZPX66
Human Metabolome Database HMDB0014496
Guide to Pharmacology 6845
KEGG C07648
PDB DX4
PharmGKB PA451663
PubChem 91669166
SureChEMBL SCHEMBL3701
ZINC ZINC000006382803
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