scopolamine   Click here for help

GtoPdb Ligand ID: 330

Synonyms: hyoscine | levo-duboisine | Scopoderm®
Approved drug PDB Ligand
scopolamine is an approved drug (FDA (1953))
Compound class: Natural product or derivative
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: scopolamine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
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]