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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL53418
CHEMBL53418
Compound Name DANTHRON
ChEMBL Synonyms Danthron | DANTRON | ISTIZIN | DORBANE | CHRYSAZIN
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names DORBANE | ISTIZIN
Molecular Formula C14H8O4

Additional synonyms for CHEMBL53418 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Oc1cccc2C(=O)c3cccc(O)c3C(=O)c12
Standard InChI InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6 ...
Download InChI
Standard InChI Key QBPFLULOKWLNNW-UHFFFAOYSA-N

Sources

  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL53418

Molecule Features

CHEMBL53418 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year
Country United States
Reason Carcinogenicity
Class Carcinogenicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoid X receptor alpha antagonist Retinoid X receptor alpha PubMed PubMed PubMed PubMed PubMed

Clinical Data

ClinicalTrials.gov DANTHRON
The Cochrane Collaboration DANTHRON

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 CHEMBL53418. 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
CHEMBL2789 Estradiol 17-beta-dehydrogenase 2 Homo sapiens 0.999
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 0.995
CHEMBL4685 Indoleamine 2,3-dioxygenase Homo sapiens 0.789
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.783
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.756
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.645
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.303
CHEMBL5491 Serine/threonine-protein kinase WEE1 Homo sapiens 0.270
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.226
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.205



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2980 Arachidonate 5-lipoxygenase Bos taurus 1.000
CHEMBL2789 Estradiol 17-beta-dehydrogenase 2 Homo sapiens 0.998
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 0.994
CHEMBL4685 Indoleamine 2,3-dioxygenase Homo sapiens 0.950
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.903
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.862
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.772
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.757
CHEMBL3243 Leukocyte common antigen Homo sapiens 0.621
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.541
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 0.461
CHEMBL4804 Dual specificity phosphatase Cdc25B Homo sapiens 0.410
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.402
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.382
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.353
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 0.307
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.289
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.245

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
240.2 240.0423 1.87 0 74.6 ACID


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.26 - 4 2.43 2 18 0.63

Structural Alerts

There are 6 structural alerts for CHEMBL53418. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A06 - DRUGS FOR CONSTIPATION
A06A - DRUGS FOR CONSTIPATION
A06AB - Contact laxatives
A06AB03 - dantron

A - ALIMENTARY TRACT AND METABOLISM
A06 - DRUGS FOR CONSTIPATION
A06A - DRUGS FOR CONSTIPATION
A06AB - Contact laxatives
A06AB53 - dantron, combinations

ChemSpider ChemSpider:QBPFLULOKWLNNW-UHFFFAOYSA-N
PubChem SID: 144204673 SID: 144208184 SID: 170465532 SID: 17389963 SID: 26747347 SID: 73151 SID: 8139970
Wikipedia Dantron

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL53418



ACToR 117-10-2
BindingDB 11316
Brenda 42878 51583 7508 27107 28096
ChEBI 3682
ChemicalBook CB4173988
DrugBank DB04816
DrugCentral 3125
eMolecules 502495
EPA CompTox Dashboard DTXSID9020328
FDA SRS Z4XE6IBF3V
Human Metabolome Database HMDB0029752
IBM Patent System D132513032268ACAFF699F65A018686F
KEGG Ligand C10312
LINCS LSM-2208
Mcule MCULE-5800615690
Metabolights MTBLC3682
MolPort MolPort-000-564-798
Nikkaji J2.905J
NMRShiftDB 30100963
PDBe CHZ
PubChem 2950
PubChem: Thomson Pharma 15121902
SureChEMBL SCHEMBL83688
ZINC ZINC000003860369

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