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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1953))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
Synonyms Click here for help
hyoscine | levo-duboisine | Scopoderm®
Database Links Click here for help
BindingDB Ligand 50015720
CAS Registry No. 114-49-8
ChEBI CHEBI:16794
ChEMBL Ligand CHEMBL569713
DrugBank Ligand DB00747
GtoPdb PubChem SID 135651031
PubChem CID 3000322
Search Google for chemical match using the InChIKey STECJAGHUSJQJN-FWXGHANASA-N
Search Google for chemicals with the same backbone STECJAGHUSJQJN
Search UniChem for chemical match using the InChIKey STECJAGHUSJQJN-FWXGHANASA-N
Search UniChem for chemicals with the same backbone STECJAGHUSJQJN
Wikipedia Scopolamine