atropine   Click here for help

GtoPdb Ligand ID: 320

Synonyms: Atropen® | hyoscyamine
Approved drug
atropine is an approved drug (FDA (1973))
Compound class: Natural product
Comment: Atropine is a muscarinic acetylcholine receptor (mAChR) antagonist.
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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: atropine

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 49.77
Molecular weight 289.17
XLogP 1.83
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)OC1CC2CCC(C1)N2C
Isomeric SMILES OCC(c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2C
InChI InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
InChI Key RKUNBYITZUJHSG-SPUOUPEWSA-N
References
1. Buckley NJ, Bonner TI, Buckley CM, Brann MR. (1989)
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.
Mol Pharmacol, 35 (4): 469-76. [PMID:2704370]
2. Carr BJ, Mihara K, Ramachandran R, Saifeddine M, Nathanson NM, Stell WK, Hollenberg MD. (2018)
Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro.
Invest Ophthalmol Vis Sci, 59 (7): 2778-2791. [PMID:29860464]
3. 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]
4. 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.
Mol Pharmacol, 53 (6): 1120-30. [PMID:9614217]
5. 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]
6. Fruchart-Gaillard C, Mourier G, Marquer C, Ménez A, Servent D. (2006)
Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7.
Mol Pharmacol, 69 (5): 1641-51. [PMID:16439611]
7. 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.
J Pharmacol Exp Ther, 297 (2): 790-7. [PMID:11303071]
8. 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]
9. Kashihara K, Varga EV, Waite SL, Roeske WR, Yamamura HI. (1992)
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
Life Sci, 51 (12): 955-71. [PMID:1325587]
10. Kovacs I, Yamamura HI, Waite SL, Varga EV, Roeske WR. (1998)
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
J Pharmacol Exp Ther, 284 (2): 500-7. [PMID:9454790]
11. Maksay G, Laube B, Betz H. (1999)
Selective blocking effects of tropisetron and atropine on recombinant glycine receptors.
J Neurochem, 73 (2): 802-6. [PMID:10428078]
12. Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I. (1999)
Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland.
Life Sci, 64 (25): 2351-8. [PMID:10374898]
13. Peralta EG, Ashkenazi A, Winslow JW, Smith DH, Ramachandran J, Capon DJ. (1987)
Distinct primary structures, ligand-binding properties and tissue-specific expression of four human muscarinic acetylcholine receptors.
EMBO J, 6 (13): 3923-9. [PMID:3443095]
14. Smith CM, Wallis RM. (1997)
Characterisation of [3H]-darifenacin as a novel radioligand for the study of muscarinic M3 receptors.
J Recept Signal Transduct Res, 17 (1-3): 177-84. [PMID:9029489]
15. Yang Z, Ney A, Cromer BA, Ng HL, Parker MW, Lynch JW. (2007)
Tropisetron modulation of the glycine receptor: femtomolar potentiation and a molecular determinant of inhibition.
J Neurochem, 100 (3): 758-69. [PMID:17181559]