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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1265
CHEMBL1265
Compound Name ADAPALENE
ChEMBL Synonyms ADAPALENE | CD 271 | DIFFERIN
Max Phase 4 (Approved)
Trade Names DIFFERIN | ADAPALENE
Molecular Formula C28H28O3

Additional synonyms for CHEMBL1265 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1ccc(cc1C23CC4CC(CC(C4)C2)C3)c5ccc6cc(ccc6c5)C(=O)O
Standard InChI InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5 ...
Download InChI
Standard InChI Key LZCDAPDGXCYOEH-UHFFFAOYSA-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


CHEMBL1265

Molecule Features

CHEMBL1265 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Over-The-Counter

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoic acid receptor agonist Retinoic acid receptor PubMed PubMed

Clinical Data

ClinicalTrials.gov ADAPALENE
The Cochrane Collaboration ADAPALENE

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 CHEMBL1265. 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
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
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 0.938
CHEMBL3979 Peroxisome proliferator-activated receptor delta Homo sapiens 0.598
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.377
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.313



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 0.972
CHEMBL3979 Peroxisome proliferator-activated receptor delta Homo sapiens 0.663
CHEMBL3864 Protein-tyrosine phosphatase 2C Homo sapiens 0.537
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.230

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
412.5 412.2038 6.68 4 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
4.23 - 8.21 5.35 3 31 0.52

Structural Alerts

There are 1 structural alerts for CHEMBL1265. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD03 - adapalene

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD53 - adapalene, combinations

ChemSpider ChemSpider:LZCDAPDGXCYOEH-UHFFFAOYSA-N
DailyMed adapalene
PubChem SID: 144205789 SID: 170464674 SID: 174006867 SID: 26758039
Wikipedia Adapalene

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1265



ACToR 106685-40-9
BindingDB 50048280
ChEBI 31174
ChemicalBook CB6771245
DrugBank DB00210
DrugCentral 87
eMolecules 901333
EPA CompTox Dashboard DTXSID5046481
FDA SRS 1L4806J2QF
Guide to Pharmacology 5429
Human Metabolome Database HMDB0014355
IBM Patent System 7F5C235B29D69B9D6824363E005EABAE
LINCS LSM-37048
Mcule MCULE-5017789384
MolPort MolPort-003-986-211
PharmGKB PA448047
PubChem 60164
PubChem: Thomson Pharma 14757761
Selleck Adapalene
SureChEMBL SCHEMBL2747
ZINC ZINC000003784182

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