ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1131
CHEMBL1131
Compound Name ACITRETIN
ChEMBL Synonyms ACITRETIN | SORIATANE | RO 10-1670/000 | NEOTIGASON | ETRETIN
Max Phase 4 (Approved)
Trade Names NEOTIGASON | ACITRETIN | SORIATANE
Molecular Formula C21H26O3

Additional synonyms for CHEMBL1131 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(C)c(\C=C\C(=C\C=C\C(=C\C(=O)O)\C)\C)c(C)c1C
Standard InChI InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3 ...
Download InChI
Standard InChI Key IHUNBGSDBOWDMA-AQFIFDHZSA-N

Sources

  • British National Formulary
  • 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


CHEMBL1131

Molecule Features

CHEMBL1131 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:Y Availability Type:Prescription-only

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
EczemaD004485HP:0000964Eczema2ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis4ATC
ClinicalTrials
DailyMed
DailyMed
DailyMed
MelanomaD008545EFO:0000756melanoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov ACITRETIN
The Cochrane Collaboration ACITRETIN

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 CHEMBL1131. 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
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 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 1.000
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.988
CHEMBL1822 Inosine-5'-monophosphate dehydrogenase 1 Homo sapiens 0.975
CHEMBL4878 Cytochrome P450 1B1 Homo sapiens 0.833
CHEMBL2231 Cytochrome P450 1A1 Homo sapiens 0.811
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 0.757
CHEMBL1075322 G-protein coupled receptor 55 Homo sapiens 0.751
CHEMBL4780 Acetylcholinesterase Torpedo californica 0.663
CHEMBL2977 Cyclooxygenase-2 Rattus norvegicus 0.626
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.586
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 0.571
CHEMBL2002 Inosine-5'-monophosphate dehydrogenase 2 Homo sapiens 0.480
CHEMBL2176859 Enoyl-[acyl-carrier-protein] reductase [NADPH] Staphylococcus aureus 0.432



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL1915 Tubulin beta-1 chain Homo sapiens 1.000
CHEMBL3378 Tumor necrosis factor receptor R1 Homo sapiens 1.000
CHEMBL3658 Tubulin alpha chain Sus scrofa 0.998
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.952
CHEMBL1075094 Nuclear factor erythroid 2-related factor 2 Homo sapiens 0.926
CHEMBL3108640 Bromodomain-containing protein 9 Homo sapiens 0.854
CHEMBL4878 Cytochrome P450 1B1 Homo sapiens 0.797
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.781
CHEMBL1822 Inosine-5'-monophosphate dehydrogenase 1 Homo sapiens 0.676
CHEMBL3194 Transthyretin Homo sapiens 0.557
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.541
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.520

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
326.4 326.1882 5.17 6 46.53 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 1 3 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.72 - 6 3.36 1 24 0.58

Structural Alerts

There are 11 structural alerts for CHEMBL1131. 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
D05BB02 - acitretin

ChemSpider ChemSpider:IHUNBGSDBOWDMA-AQFIFDHZSA-N
DailyMed acitretin
PubChem SID: 144205565 SID: 26756475 SID: 29216416 SID: 49640651
Wikipedia Acitretin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1131



ACToR 54757-46-9 55079-83-9
BindingDB 50088429
Brenda 145956 31766 145043
ChEBI 50173
ChemicalBook CB7184686
DrugBank DB00459
DrugCentral 78
eMolecules 1935682
EPA CompTox Dashboard DTXSID6022553
FDA SRS LCH760E9T7
Guide to Pharmacology 7598
LINCS LSM-43217
MolPort MolPort-003-925-892
NIH Clinical Collection SAM002589973
Nikkaji J23.289K J261.795A
PubChem 5284513
PubChem: Drugs of the Future 12013101
PubChem: Thomson Pharma 14899611
Selleck Acitretin
SureChEMBL SCHEMBL3759
ZINC ZINC000003798734

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