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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL464
CHEMBL464
Compound Name ETRETINATE
ChEMBL Synonyms TIGASON | ETRETINATE | TEGISON | RO 10-9359
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names TEGISON | TIGASON
Molecular Formula C23H30O3

Additional synonyms for CHEMBL464 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCOC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\c1c(C)cc(OC)c(C)c1C
Standard InChI InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-2 ...
Download InChI
Standard InChI Key HQMNCQVAMBCHCO-DJRRULDNSA-N

Sources

  • British National Formulary
  • Orange Book
  • 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  • Withdrawn Drugs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


CHEMBL464

Molecule Features

CHEMBL464 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1989
Country France; United States
Reason Risk for birth defects
Class Teratogenicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoid receptor agonist Retinoid receptor PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
PsoriasisD011565EFO:0000676psoriasis4ATC

Clinical Data

ClinicalTrials.gov ETRETINATE
The Cochrane Collaboration ETRETINATE

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 CHEMBL464. 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
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 0.999
CHEMBL2857 Human rhinovirus A protease Human rhinovirus sp. 0.982
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 0.974
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.971
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.899
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.871
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.811
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.807
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.747
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.647
CHEMBL2392 DNA polymerase beta Homo sapiens 0.609
CHEMBL1075322 G-protein coupled receptor 55 Homo sapiens 0.609
CHEMBL1822 Inosine-5'-monophosphate dehydrogenase 1 Homo sapiens 0.585



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL1915 Tubulin beta-1 chain Homo sapiens 0.999
CHEMBL3658 Tubulin alpha chain Sus scrofa 0.973
CHEMBL3378 Tumor necrosis factor receptor R1 Homo sapiens 0.878
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.871
CHEMBL5162 Neuropeptide S receptor Homo sapiens 0.850
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.836
CHEMBL2857 Human rhinovirus A protease Human rhinovirus sp. 0.793
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.772
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.671
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.647
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 0.642
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.634

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
354.5 354.2195 5.65 7 35.53 -


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 0 1 3 0 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - 7.15 7.15 1 26 0.36

Structural Alerts

There are 14 structural alerts for CHEMBL464. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D05 - ANTIPSORIATICS
D05B - ANTIPSORIATICS FOR SYSTEMIC USE
D05BB - Retinoids for treatment of psoriasis
D05BB01 - etretinate

ChemSpider ChemSpider:HQMNCQVAMBCHCO-DJRRULDNSA-N
PubChem SID: 144206054 SID: 170465372 SID: 50112753
Wikipedia Etretinate

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL464



ACToR 54350-48-0
Brenda 106049
ChEBI 4913
ChemicalBook CB6214647
DrugCentral 1116
eMolecules 17497555
EPA CompTox Dashboard DTXSID0023036
FDA SRS 65M2UDR9AG
Guide to Pharmacology 7599
LipidMaps LMPR01090046
MolPort MolPort-005-937-301
Nikkaji J2.786C J23.610A
PubChem 5282375
PubChem: Drugs of the Future 12013448
PubChem: Thomson Pharma 14754444
SureChEMBL SCHEMBL3123
ZINC ZINC000003830820

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