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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1425
CHEMBL1425
Compound Name MERCAPTOPURINE
ChEMBL Synonyms PURI-NETHOL | PURINETHOL | PURIXAN | MERCAPTOPURINE | Mercaptopurine anhydrous | XALUPRINE
Max Phase 4 (Approved)
Trade Names MERCAPTOPURINE | PURIXAN | PURI-NETHOL | PURINETHOL | XALUPRINE
Molecular Formula C5H4N4S

Additional synonyms for CHEMBL1425 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Sc1ncnc2nc[nH]c12
Standard InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9 ...
Download InChI
Standard InChI Key GLVAUDGFNGKCSF-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • 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


CHEMBL1425

Molecule Features

CHEMBL1425 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:Y Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Amidophosphoribosyltransferase inhibitor Amidophosphoribosyltransferase DailyMed PubMed
DNA inhibitor DNA DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Crohn DiseaseD003424EFO:0000384Crohn's disease3ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
ColitisD003092EFO:0003872colitis2ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia3ClinicalTrials
OligodendrogliomaD009837EFO:0002501anaplastic oligodendroglioma2ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma2ClinicalTrials
Histiocytosis, Langerhans-CellD006646EFO:1000318Langerhans Cell Histiocytosis2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000094B-cell acute lymphoblastic leukemia1ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia1ClinicalTrials
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis3ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials

Clinical Data

ClinicalTrials.gov MERCAPTOPURINE
The Cochrane Collaboration MERCAPTOPURINE

Metabolites for CHEMBL1425

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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 CHEMBL1425. 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
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 0.997
CHEMBL1929 Xanthine dehydrogenase Homo sapiens 0.995
CHEMBL4941 S-methyl-5-thioadenosine phosphorylase Homo sapiens 0.994
CHEMBL5260 Serine/threonine-protein kinase TNNI3K Homo sapiens 0.973
CHEMBL2148 Tyrosine-protein kinase JAK3 Homo sapiens 0.969
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 0.751
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.342
CHEMBL5605 Mitogen-activated protein kinase kinase kinase 7-interacting protein 1 Homo sapiens 0.331



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4338 Purine nucleoside phosphorylase Homo sapiens 1.000
CHEMBL5648 Purine nucleoside phosphorylase Plasmodium falciparum 1.000
CHEMBL2864 6-O-methylguanine-DNA methyltransferase Homo sapiens 0.998
CHEMBL1929 Xanthine dehydrogenase Homo sapiens 0.998
CHEMBL4941 S-methyl-5-thioadenosine phosphorylase Homo sapiens 0.994
CHEMBL2148 Tyrosine-protein kinase JAK3 Homo sapiens 0.994
CHEMBL5260 Serine/threonine-protein kinase TNNI3K Homo sapiens 0.989
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 0.986
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 0.921
CHEMBL2605 Adenosine A2a receptor Cavia porcellus 0.904
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.897
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 0.832
CHEMBL2935 Purine nucleoside phosphorylase Bos taurus 0.775
CHEMBL2360 Hypoxanthine-guanine phosphoribosyltransferase Homo sapiens 0.436
CHEMBL4702 Dopamine beta-hydroxylase Bos taurus 0.402
CHEMBL6172 D-amino-acid oxidase Sus scrofa 0.365
CHEMBL5605 Mitogen-activated protein kinase kinase kinase 7-interacting protein 1 Homo sapiens 0.358
CHEMBL2573 P-glycoprotein 3 Mus musculus 0.322

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
152.2 152.0157 0.64 0 54.46 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
-.26 8.71 -.22 -3.09 2 10 0.43

Structural Alerts

There are 5 structural alerts for CHEMBL1425. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BB - Purine analogues
L01BB02 - mercaptopurine

ChemSpider ChemSpider:GLVAUDGFNGKCSF-UHFFFAOYSA-N
DailyMed mercaptopurine
PubChem SID: 124891196 SID: 144204709 SID: 144209789 SID: 170464985 SID: 174006957 SID: 26748122 SID: 49675007 SID: 50086850 SID: 538245
Wikipedia Mercaptopurine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1425



ACToR 50-44-2
Atlas mercaptopurine
BindingDB 50423778
Brenda 12401 112781 46631 30171 105222 1345 157386 105221
ChEBI 94796 2208 50667
ChemicalBook CB1425059
DrugBank DB01033
DrugCentral 1708
eMolecules 729201 1061194 525836 32176559 1987653
EPA CompTox Dashboard DTXSID0020810
FDA SRS PKK6MUZ20G
Guide to Pharmacology 7226
Human Metabolome Database HMDB0015167
IBM Patent System 4CC5831781A3C15C7A6E3FAF64695EF3
KEGG Ligand C02380 C01756
LINCS LSM-5963
Mcule MCULE-4811219863
MolPort MolPort-001-815-626 MolPort-006-167-688 MolPort-001-783-696 MolPort-003-846-751 MolPort-003-665-491
NIH Clinical Collection SAM002589937
Nikkaji J2.298E
PDBe PM6
PharmGKB PA450379
PubChem 667490
PubChem: Thomson Pharma 14772317 15970891 15321640
Rhea 50667
Selleck Mercaptopurine
SureChEMBL SCHEMBL3893
ZINC ZINC000004658290

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