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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: scopolamine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
1. Bolden C, Cusack B, Richelson E. (1992)
Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells.
J Pharmacol Exp Ther, 260 (2): 576-80. [PMID:1346637]
2. Croy CH, Chan WY, Castetter AM, Watt ML, Quets AT, Felder CC. (2016)
Characterization of PCS1055, a novel muscarinic M4 receptor antagonist.
Eur J Pharmacol, 782: 70-6. [PMID:27085897]
3. Huang F, Buchwald P, Browne CE, Farag HH, Wu WM, Ji F, Hochhaus G, Bodor N. (2001)
Receptor binding studies of soft anticholinergic agents.
AAPS PharmSci, 3 (4): E30. [PMID:12049493]