adapalene   

GtoPdb Ligand ID: 5429

Synonyms: Differin®
adapalene is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Adapalene is a third-generation topical anti-acne retinoid.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 46.53
Molecular weight 412.2
XLogP 8.57
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
Isomeric SMILES COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
InChI InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
InChI Key LZCDAPDGXCYOEH-UHFFFAOYSA-N
References
1. Charpentier B, Bernardon JM, Eustache J, Millois C, Martin B, Michel S, Shroot B. (1995)
Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes.
J. Med. Chem., 38 (26): 4993-5006. [PMID:8544175]