scopolamine   Click here for help

GtoPdb Ligand ID: 330

Synonyms: hyoscine | levo-duboisine | Scopoderm®
Approved drug
scopolamine is an approved drug (FDA (1953))
Comment: There is no exact match in PubChem for the structure that we show here. However, there is activity data listed against CID 3000322, which has different stereochemistry. Our structure and its stereochemistry is in consensus with the entries on the databases linked to above.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 62.3
Molecular weight 303.15
XLogP 0.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC(c1ccccc1)C(=O)OC1CC2N(C(C1)C1C2O1)C
Isomeric SMILES OC[C@H](c1ccccc1)C(=O)O[C@@H]1C[C@H]2N([C@@H](C1)[C@H]1[C@@H]2O1)C
InChI InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
InChI Key STECJAGHUSJQJN-FWXGHANASA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
M3 receptor Hs Antagonist Antagonist 9.4 pKi - 1,3
pKi 9.4 [1,3]
M4 receptor Hs Antagonist Antagonist 9.1 – 9.5 pKi - 1,3
pKi 9.1 – 9.5 [1,3]
M1 receptor Primary target of this compound Hs Antagonist Antagonist 9.0 pKi - 2-3
pKi 9.0 [2-3]
M2 receptor Hs Antagonist Antagonist 8.7 pKi - 1,3
pKi 8.7 [1,3]
M5 receptor Hs Antagonist Antagonist 8.7 pKi - 1
pKi 8.7 [1]