ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1466
CHEMBL1466
Compound Name DICUMAROL
ChEMBL Synonyms DICOUMAROL | DICUMAROL | BISHYDROXYCOUMARIN
Max Phase 4 (Approved)
Trade Names Dicumarol
Molecular Formula C19H12O6

Additional synonyms for CHEMBL1466 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OC1=C(CC2=C(O)c3ccccc3OC2=O)C(=O)Oc4ccccc14
Standard InChI InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-1 ...
Download InChI
Standard InChI Key DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1466

Molecule Features

CHEMBL1466 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:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor Vitamin k epoxide reductase complex subunit 1 isoform 1 PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
THROMBOSISD013927HP:0004419RECURRENT THROMBOPHLEBITIS4ATC

Clinical Data

ClinicalTrials.gov DICUMAROL
The Cochrane Collaboration DICUMAROL

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 CHEMBL1466. 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
CHEMBL3623 Quinone reductase 1) Homo sapiens 1.000
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.984
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.984
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.961
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.847
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.666
CHEMBL335 Protein-tyrosine phosphatase 1B Homo sapiens 0.638
CHEMBL1900 Aldose reductase Homo sapiens 0.627
CHEMBL2392 DNA polymerase beta Homo sapiens 0.534
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.433
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.389
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.382
CHEMBL2622 Aldose reductase Rattus norvegicus 0.358
CHEMBL4234 Estradiol 17-beta-dehydrogenase 3 Homo sapiens 0.339
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.322
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.270
CHEMBL5514 Huntingtin Homo sapiens 0.240
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.231



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3623 Quinone reductase 1) Homo sapiens 1.000
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.988
CHEMBL2622 Aldose reductase Rattus norvegicus 0.950
CHEMBL1293255 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens 0.815
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.789
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.669
CHEMBL2392 DNA polymerase beta Homo sapiens 0.594
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.538
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.536
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.503
CHEMBL1900 Aldose reductase Homo sapiens 0.494
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.472
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.439
CHEMBL1287620 Fructose-bisphosphate aldolase Mycobacterium tuberculosis 0.402
CHEMBL5514 Huntingtin Homo sapiens 0.372
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.360
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.343
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.342
CHEMBL5162 Neuropeptide S receptor Homo sapiens 0.305
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.271

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
336.3 336.0634 2.79 2 93.06 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.2 - 2.05 -1 2 25 0.65

Structural Alerts

There are 3 structural alerts for CHEMBL1466. To view alerts please click here.

Compound Cross References

ATC B - BLOOD AND BLOOD FORMING ORGANS
B01 - ANTITHROMBOTIC AGENTS
B01A - ANTITHROMBOTIC AGENTS
B01AA - Vitamin K antagonists
B01AA01 - dicoumarol

ChemSpider ChemSpider:DOBMPNYZJYQDGZ-UHFFFAOYSA-N
PubChem SID: 11112184 SID: 144203908 SID: 170465275
Wikipedia Dicoumarol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1466



ACToR 66-76-2
BindingDB 35525
Brenda 44040 38649 15728 18884 754 75518 3265 36949
ChEBI 4513
DrugBank DB00266
DrugCentral 867
eMolecules 591595
EPA CompTox Dashboard DTXSID8021729
FDA SRS 7QID3E7BG7
Guide to Pharmacology 6808
Human Metabolome Database HMDB0014411
IBM Patent System 5CD84693C0C5F1E9E6DCBEFCEBFBB2D8
KEGG Ligand C00796
LINCS LSM-45761
Mcule MCULE-8095183287
MolPort MolPort-000-422-589
Nikkaji J4.845C
PubChem 54676038
PubChem: Thomson Pharma 14851261
SureChEMBL SCHEMBL33891
ZINC ZINC000003869855

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