imiquimod   

GtoPdb Ligand ID: 5003

Synonyms: Aldara® | R837 | S-26308 | Zyclara®
imiquimod is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Imiquimod is a TLR7 agonist acting as an immunomodulator.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 56.73
Molecular weight 240.14
XLogP 2.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(Cn1cnc2c1c1ccccc1nc2N)C
Isomeric SMILES CC(Cn1cnc2c1c1ccccc1nc2N)C
InChI InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
InChI Key DOUYETYNHWVLEO-UHFFFAOYSA-N
References
1. Larson P, Kucaba TA, Xiong Z, Olin M, Griffith TS, Ferguson DM. (2017)
Design and Synthesis of N1-Modified Imidazoquinoline Agonists for Selective Activation of Toll-like Receptors 7 and 8.
ACS Med Chem Lett, 8 (11): 1148-1152. [PMID:29152046]