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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL727
CHEMBL727
Compound Name THIOGUANINE
ChEMBL Synonyms Tabloid | LANVIS | TIOGUANINE | THIOGUANINE
Max Phase 4 (Approved)
Trade Names THIOGUANINE | LANVIS | Tabloid
Molecular Formula C5H5N5S

Additional synonyms for CHEMBL727 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=Nc2[nH]cnc2C(=S)N1
Standard InChI InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8, ...
Download InChI
Standard InChI Key WYWHKKSPHMUBEB-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL727

Molecule Features

CHEMBL727 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA FDA
Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor Inosine-5'-monophosphate dehydrogenase (IMPDH) FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder3ClinicalTrials
Histiocytosis, Langerhans-CellD006646EFO:1000318Langerhans Cell Histiocytosis2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma2ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials

Clinical Data

ClinicalTrials.gov THIOGUANINE
The Cochrane Collaboration THIOGUANINE

Metabolites for CHEMBL727

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL727. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 1.000
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 1.000
CHEMBL2360 Hypoxanthine-guanine phosphoribosyltransferase Homo sapiens 1.000
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 0.995
CHEMBL3972 GAR transformylase Homo sapiens 0.782
CHEMBL6166 Mitogen-activated protein kinase kinase kinase kinase 4 Homo sapiens 0.442
CHEMBL3267 PI3-kinase p110-gamma subunit Homo sapiens 0.307
CHEMBL4941 S-methyl-5-thioadenosine phosphorylase Homo sapiens 0.300
CHEMBL2163176 Lysine-specific demethylase 5C Homo sapiens 0.277
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 0.222



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 1.000
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 1.000
CHEMBL2360 Hypoxanthine-guanine phosphoribosyltransferase Homo sapiens 1.000
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 1.000
CHEMBL3559681 2-amino-4-hydroxy-6-hydroxymethyldihydropteridin e pyrophosphokinase Staphylococcus aureus 0.998
CHEMBL3267 PI3-kinase p110-gamma subunit Homo sapiens 0.965
CHEMBL2163176 Lysine-specific demethylase 5C Homo sapiens 0.876
CHEMBL5896 Lysine-specific demethylase 4A Homo sapiens 0.744
CHEMBL2605 Adenosine A2a receptor Cavia porcellus 0.684
CHEMBL3972 GAR transformylase Homo sapiens 0.625
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.552
CHEMBL3313832 Lysine-specific demethylase 4B Homo sapiens 0.499
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 0.383
CHEMBL3774295 Lysine-specific demethylase 5B Homo sapiens 0.319
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 0.260
CHEMBL4941 S-methyl-5-thioadenosine phosphorylase Homo sapiens 0.257
CHEMBL5648 Purine nucleoside phosphorylase Plasmodium falciparum 0.241
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.201

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
167.2 167.0266 0.6 0 83.38 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 3 0 5 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.79 2.45 -.54 -1.5 2 11 0.5

Structural Alerts

There are 2 structural alerts for CHEMBL727. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BB - Purine analogues
L01BB03 - tioguanine

ChemSpider ChemSpider:WYWHKKSPHMUBEB-UHFFFAOYSA-N
PubChem SID: 144204586 SID: 144206735 SID: 144209599 SID: 144210595 SID: 170464908 SID: 174007001 SID: 26748270 SID: 538243 SID: 57260104 SID: 57264437
Wikipedia Tioguanine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL727



ACToR 154-42-7
Atlas tioguanine
BindingDB 50200099
Brenda 29358 14340 29360 45935 1253 51290
ChEBI 9555
DrugBank DB00352
DrugCentral 2632
eMolecules 1056735 5753682 1989215 10169597 532358
EPA CompTox Dashboard DTXSID6023652
FDA SRS WIX31ZPX66
Guide to Pharmacology 6845
Human Metabolome Database HMDB0014496
IBM Patent System 96FC71C4FA5FCFB7B6FA48AD5C1BDBEE 68DF1FA7032814C3C683A9EC43FC7D89
KEGG Ligand C07648
LINCS LSM-6723
Mcule MCULE-5787306636
MolPort MolPort-000-929-106 MolPort-001-813-204 MolPort-003-665-495
Nikkaji J21.274A
PDBe DX4
PharmGKB PA451663
PubChem 2723601
PubChem: Thomson Pharma 14772534 49749672 16902289 15171129
Rhea 9555
Selleck Thioguanine
SureChEMBL SCHEMBL3701
ZINC ZINC000006382803

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WYWHKKSPHMUBEB-UHFFFAOYSA-N spacer
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