acetylcholine   Click here for help

GtoPdb Ligand ID: 294

Synonyms: ACh | E1001 | O-acetylcholine
PDB Ligand
Compound class: Metabolite or derivative
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: acetylcholine

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 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
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 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
InChI Key OIPILFWXSMYKGL-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
M1 receptor
M2 receptor
M3 receptor
M4 receptor
M5 receptor
nicotinic acetylcholine receptor α10 subunit
nicotinic acetylcholine receptor α1 subunit
nicotinic acetylcholine receptor α2 subunit
nicotinic acetylcholine receptor α3 subunit
nicotinic acetylcholine receptor α4 subunit
nicotinic acetylcholine receptor α5 subunit
nicotinic acetylcholine receptor α6 subunit
nicotinic acetylcholine receptor α7 subunit
nicotinic acetylcholine receptor α9 subunit
nicotinic acetylcholine receptor β1 subunit
nicotinic acetylcholine receptor β2 subunit
nicotinic acetylcholine receptor β3 subunit
nicotinic acetylcholine receptor β4 subunit
nicotinic acetylcholine receptor δ subunit
nicotinic acetylcholine receptor ε subunit
nicotinic acetylcholine receptor γ subunit
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
butyrylcholinesterase 3.1.1.7 Acetylcholine + H2O = acetic acid + choline + H+
choline O-acetyltransferase 2.3.1.6 Acetyl CoA + choline = acetylcholine + coenzyme A
acetylcholinesterase (Yt blood group) 3.1.1.7 Acetylcholine + H2O = acetic acid + choline + H+
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Vesicular acetylcholine transporter 1,5
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
M2 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.4 pKi - 6
⤷ pKi 6.4 [6]
M5 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.1 pKi - 2
⤷ pKi 6.1 [2]
M3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 5.6 pKi - 2
⤷ pKi 5.6 [2]
M2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.3 – 6.5 pKi - 2-4
⤷ pKi 4.3 – 6.5 [2-4]
M4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.5 – 5.6 pKi - 3-4
⤷ pKi 4.5 – 5.6 [3-4]
M1 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 5.0 pKi - 2
⤷ pKi 5.0 [2]
M3 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.5 – 5.4 pKi - 2-4
⤷ pKi 4.5 – 5.4 [2-4]
M1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.3 – 4.9 pKi - 3-4
⤷ pKi 4.3 – 4.9 [3-4]
Ligand mentioned in the following text fields
Acetylcholine receptors (muscarinic) overview
Choline transporter overview