acetylcholine   Click here for help

GtoPdb Ligand ID: 294

Synonyms: ACh | E1001 | O-acetylcholine
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 26.3
Molecular weight 146.12
XLogP -0.1
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)OCC[N+](C)(C)C
Isomeric SMILES CC(=O)OCC[N+](C)(C)C
InChI InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
1. Bravo DT, Kolmakova NG, Parsons SM. (2004)
Choline is transported by vesicular acetylcholine transporter.
J Neurochem, 91 (3): 766-8. [PMID:15485505]
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. 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]
4. Keov P, Valant C, Devine SM, Lane JR, Scammells PJ, Sexton PM, Christopoulos A. (2013)
Reverse engineering of the selective agonist TBPB unveils both orthosteric and allosteric modes of action at the M₁ muscarinic acetylcholine receptor.
Mol Pharmacol, 84 (3): 425-37. [PMID:23798605]
5. Khare P, Ojeda AM, Chandrasekaran A, Parsons SM. (2010)
Possible important pair of acidic residues in vesicular acetylcholine transporter.
Biochemistry, 49 (14): 3049-59. [PMID:20225888]
6. 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]