atropine   

GtoPdb Ligand ID: 320

Synonyms: Atropen® | hyoscyamine
atropine is an approved drug (FDA (1973))
Comment: Atropine is a muscarinic acetylcholine receptor (mAChR) antagonist.
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2D Structure
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Physico-chemical Properties
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
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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
M4 receptor Rn Antagonist Antagonist 9.7 pKi - 9
pKi 9.7 [9]
M5 receptor Hs Antagonist Antagonist 9.3 – 9.7 pKi - 1,7
pKi 9.3 – 9.7 [1,7]
M5 receptor Rn Antagonist Antagonist 9.4 pKi - 9
pKi 9.4 [9]
M1 receptor Rn Antagonist Antagonist 9.0 – 9.7 pKi - 1,3,9
pKi 9.0 – 9.7 [1,3,9]
M3 receptor Hs Antagonist Antagonist 8.9 – 9.8 pKi - 1,5,7-8,13-14
pKi 8.9 – 9.8 [1,5,7-8,13-14]
M4 receptor Hs Antagonist Antagonist 8.7 – 9.9 pKi - 1-2,7-8,13
pKi 9.9 (Ki 1.4x10-10 M) [2]
pKi 8.7 – 9.5 [1,7-8,13]
M1 receptor Hs Antagonist Antagonist 8.5 – 9.6 pKi - 4,6-8,13-14
pKi 8.5 – 9.6 [4,6-8,13-14]
M2 receptor Rn Antagonist Antagonist 9.0 – 9.1 pKi - 9-10
pKi 9.0 – 9.1 [9-10]
M3 receptor Rn Antagonist Antagonist 8.7 – 9.3 pKi - 3,9
pKi 8.7 – 9.3 [3,9]
M2 receptor Hs Antagonist Antagonist 7.8 – 9.2 pKi - 1,3,7-8,10,12-13
pKi 7.8 – 9.2 [1,3,7-8,10,12-13]
α2A-adrenoceptor Hs Antagonist Antagonist 4.8 pKi - 2
pKi 4.8 (Ki 1.4x10-5 M) [2]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Glycine Receptor (All subtypes) N/A Subunit-specific Inhibition - - < 1x10-6 11
Conc range: < 1x10-6 M α2 > α1 [11]
Glycine Receptor (All subtypes) Hs Antagonist Antagonist 3.6 pIC50 - 11,15
pIC50 3.6 [11,15]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields