[3H]N-methyl scopolamine   Click here for help

GtoPdb Ligand ID: 317

Synonyms: [3H]N-methylscopolamine | [3H]NMS
 Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic
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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
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 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 59.06
Molecular weight 318.17
XLogP 0.59
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)OC1CC2C3C(C(C1)[N+]2(C)C)O3
Isomeric SMILES OC[C@H](c1ccccc1)C(=O)OC1C[C@@H]2[C@@H]3[C@H]([C@H](C1)[N+]2(C)C)O3
InChI InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12?,13-,14-,15+,16-,17+/m1/s1
InChI Key LZCOQTDXKCNBEE-XJMZPCNVSA-N
References
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Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
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2. Cheng K, Khurana S, Chen Y, Kennedy RH, Zimniak P, Raufman JP. (2002)
Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist.
J Pharmacol Exp Ther, 303 (1): 29-35. [PMID:12235229]
3. Christopoulos A, Pierce TL, Sorman JL, El-Fakahany EE. (1998)
On the unique binding and activating properties of xanomeline at the M1 muscarinic acetylcholine receptor.
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4. Christopoulos A, Wilson K. (2001)
Interaction of anandamide with the M(1) and M(4) muscarinic acetylcholine receptors.
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5. Hirose H, Aoki I, Kimura T, Fujikawa T, Numazawa T, Sasaki K, Sato A, Hasegawa T, Nishikibe M, Mitsuya M et al.. (2001)
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
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6. Jakubík J, Bacáková L, el-Fakahany EE, Tucek S. (1995)
Subtype selectivity of the positive allosteric action of alcuronium at cloned M1-M5 muscarinic acetylcholine receptors.
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7. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
8. Jakubík J, El-Fakahany EE, Dolezal V. (2006)
Differences in kinetics of xanomeline binding and selectivity of activation of G proteins at M(1) and M(2) muscarinic acetylcholine receptors.
Mol Pharmacol, 70 (2): 656-66. [PMID:16675658]
9. Jolkkonen M, van Giersbergen PL, Hellman U, Wernstedt C, Karlsson E. (1994)
A toxin from the green mamba Dendroaspis angusticeps: amino acid sequence and selectivity for muscarinic m4 receptors.
FEBS Lett, 352 (1): 91-4. [PMID:7925952]
10. Khattar SK, Bora RS, Priyadarsiny P, Gupta D, Khanna A, Narayanan KL, Babu V, Chugh A, Saini KS. (2006)
High level stable expression of pharmacologically active human M1-M5 muscarinic receptor subtypes in mammalian cells.
Biotechnol Lett, 28 (2): 121-9. [PMID:16369696]
11. Lazareno S, Birdsall NJ. (1995)
Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: interactions of strychnine and acetylcholine at muscarinic receptors.
Mol Pharmacol, 48 (2): 362-78. [PMID:7651370]
12. Stein R, Pinkas-Kramarski R, Sokolovsky M. (1988)
Cloned M1 muscarinic receptors mediate both adenylate cyclase inhibition and phosphoinositide turnover.
EMBO J, 7 (10): 3031-5. [PMID:2846274]
13. Vuckovic Z, Gentry PR, Berizzi AE, Hirata K, Varghese S, Thompson G, van der Westhuizen ET, Burger WAC, Rahmani R, Valant C et al.. (2019)
Crystal structure of the M5 muscarinic acetylcholine receptor.
Proc Natl Acad Sci USA, 116 (51): 26001-26007. [PMID:31772027]
14. Wang SZ, el-Fakahany EE. (1993)
Application of transfected cell lines in studies of functional receptor subtype selectivity of muscarinic agonists.
J Pharmacol Exp Ther, 266 (1): 237-43. [PMID:7687290]