Compound Detail

CHEMBL667

ACETYLCHOLINE

💊 Approved Drug

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💊 Approved Drug

CC(=O)OCC[N+](C)(C)C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL667
Name	ACETYLCHOLINE
Phase	Approved
Structure Type	MOL
InChI Key	OIPILFWXSMYKGL-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Acetylcholine

Targets

170

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

146.2

MW (Da)

0.26

ALogP

HBA

HBD

26.3

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1973
Availability	Prescription
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product

Extended Properties

Molecular Formula	C7H16NO2+
MW	146.21
Aromatic Rings	0
Heavy Atoms	10
NP-Likeness	1.19

Indications

Glaucoma Anemia Anemia, Sickle Cell Diabetes Mellitus, Type 2 Coronary Disease HIV Infections Inflammation Ischemia

ATC Classification

S01EB09

acetylcholine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

EC50 109 meas. best 8.96

Ki 49 meas. best 8.12

IC50 10 meas. best 7.92

Kd 2 meas. best 4.76

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Muscarinic acetylcholine receptor M1 CHEMBL216	EC50	8.96	6.4292	1.1	13
Muscarinic acetylcholine receptor M5 CHEMBL2035	EC50	8.92	7.718	1.2	5
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907589	EC50	8.77	5.4927	1.7	11
Muscarinic acetylcholine receptor M3 CHEMBL245	EC50	8.49	7.3113	3.2	8
Muscarinic acetylcholine receptor M2 CHEMBL211	EC50	8.15	6.9177	7.0	13
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	Ki	8.12	7.5275	7.6	8
Muscarinic acetylcholine receptor M4 CHEMBL1821	EC50	8.0	7.465	10.0	6
Neuronal acetylcholine receptor; alpha2/beta2 CHEMBL1907592	Ki	7.96	7.96	11.0	1
Muscarinic acetylcholine receptor CHEMBL1907609	IC50	7.92	6.27	12.0	6
Neuronal acetylcholine receptor; alpha3/beta2 CHEMBL1907587	Ki	7.39	7.39	41.0	1
Neuronal acetylcholine receptor CHEMBL2094110	Ki	7.37	7.37	43.0	1
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	Ki	7.24	7.208	57.5	5
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	7.07	7.07	85.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.87	6.87	134.9	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.8	6.5125	158.5	4
Unchecked CHEMBL612545	Ki	6.75	5.525	180.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	Ki	6.3	5.7	501.2	2
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	Ki	6.21	6.17	616.6	7
Aorta CHEMBL613606	IC50	6.0	6.0	1000.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	EC50	5.51	5.51	3120.0	1
Acetylcholine-binding protein CHEMBL6084	Ki	5.5	5.35	3162.3	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL4980	Ki	5.46	5.03	3509.0	2
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	EC50	5.4	4.74	3981.1	9
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	5.33	5.205	4700.0	4
Acetylcholine receptor subunit delta CHEMBL3916	EC50	5.3	5.3	5000.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	5.24	4.858	5800.0	5
Unchecked CHEMBL612545	EC50	5.2	4.4163	6360.0	8
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907593	EC50	5.1	5.0775	7943.3	4
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	5.07	5.07	8511.4	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	5.01	5.01	9772.4	1
Nicotinic acetylcholine receptor alpha8 subunit CHEMBL2366437	EC50	4.94	4.94	11481.5	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Kd	4.76	4.76	17378.0	2
Neuronal acetylcholine receptor; alpha4/beta4 CHEMBL1907595	EC50	4.72	4.72	19000.0	1
Neuronal acetylcholine receptor; alpha3/beta4 CHEMBL1907594	EC50	4.72	4.6467	19000.0	3
Neuronal acetylcholine receptor; alpha4/beta2 CHEMBL1907596	EC50	4.62	4.34	24000.0	2
Neuronal acetylcholine receptor subunit alpha-9 CHEMBL2184	EC50	4.58	4.58	26000.0	1
Neuronal acetylcholine receptor; alpha9/alpha10 CHEMBL2109238	EC50	4.52	4.52	30000.0	1
Neuronal acetylcholine receptor CHEMBL2094110	EC50	4.4	4.4	40000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	0.0001	hr	Gallus gallus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Muscarinic acetylcholine receptor M1	EC50	=	1.1	nM	8.96	Agonist activity at human M1 receptor expressed in CHO-K1 cells assessed as calc...	22677319
Muscarinic acetylcholine receptor M1	EC50	=	1.1	nM	8.96	Agonist activity at human muscarinic M1 receptor expressed in CHO-K1 cells asses...	20684563
Muscarinic acetylcholine receptor M5	EC50	=	1.2	nM	8.92	Agonist activity at human muscarinic M5 receptor expressed in BHK-21 cells asses...	20684563
Muscarinic acetylcholine receptor M5	EC50	=	1.2	nM	8.92	Agonist activity at human muscarinic M5 receptor expressed in BHK-21 cells asses...	22677319
Neuronal acetylcholine receptor; alpha4/beta2	EC50	=	1.7	nM	8.77	Activation of alpha4beta2* nAChR high affinity site (unknown origin) expressed i...	24901260
Muscarinic acetylcholine receptor M3	EC50	=	3.2	nM	8.49	Agonist activity at human muscarinic M3 receptor expressed in BHK-21 cells asses...	20684563
Muscarinic acetylcholine receptor M3	EC50	=	3.2	nM	8.49	Agonist activity at human muscarinic M3 receptor expressed in BHK-21 cells asses...	22677319
Muscarinic acetylcholine receptor M2	EC50	=	7.0	nM	8.15	Agonist activity at human muscarinic M2 receptor expressed in CHO cells after 30...	26299349
Neuronal acetylcholine receptor; alpha4/beta2	Ki	=	7.6	nM	8.12	Displacement of [3H]-cytisine from Alpha4-beta2 Nicotinic acetylcholine receptor...	16078832
Muscarinic acetylcholine receptor M4	EC50	=	10.0	nM	8.0	Agonist activity at human muscarinic M4 receptor expressed in BHK-21 cells coexp...	20684563
Muscarinic acetylcholine receptor M4	EC50	=	10.0	nM	8.0	Agonist activity at muscarinic human M4 receptor expressed in BHK-21 cells asses...	22677319
Neuronal acetylcholine receptor; alpha2/beta2	Ki	=	11.0	nM	7.96	Binding affinity towards rat nicotinic acetylcholine receptor alpha2-beta2 expre...	15050613
Muscarinic acetylcholine receptor	IC50	=	12.0	nM	7.92	Compound was tested in vitro for its binding affinity to muscarinic acetylcholin...	1560440
Muscarinic acetylcholine receptor	IC50	=	12.0	nM	7.92	The compound was tested in vitro for central muscarinic acetylcholine receptor a...	1895293
Muscarinic acetylcholine receptor	IC50	=	12.0	nM	7.92	In vitro ability to displace [3H]oxotremorine-M (OXO-M) from rat cerebral cortex...	1619616
Muscarinic acetylcholine receptor M2	EC50	=	12.59	nM	7.9	Agonist activity at recombinant human muscarinic M2 receptor expressed in CHO ce...	29094937
Muscarinic acetylcholine receptor M2	EC50	=	13.0	nM	7.89	Agonist activity at recombinant human muscarinic M2 receptor expressed in CHO ce...	29094937
Muscarinic acetylcholine receptor M5	EC50	=	19.1	nM	7.72	Agonist activity at human muscarinic M5 receptor expressed in CHO cells after 30...	26299349
Muscarinic acetylcholine receptor M3	EC50	=	23.0	nM	7.64	Agonist activity at recombinant human muscarinic M3 receptor expressed in CHO ce...	29094937
Muscarinic acetylcholine receptor M3	EC50	=	22.91	nM	7.64	Agonist activity at recombinant human muscarinic M3 receptor expressed in CHO ce...	29094937

Literature References

PubMed	DOI	Target Context	# Activities
29094937	10.1021/acs.jmedchem.7b01113	Muscarinic acetylcholine receptor M2	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
17722904	10.1021/jm070574f	Unchecked	11
15050620	10.1016/j.bmcl.2004.01.004	HEK293	9
35576655	10.1016/j.bmc.2022.116811	RAW264.7	8
29094937	10.1021/acs.jmedchem.7b01113	Muscarinic acetylcholine receptor M1	7
29094937	10.1021/acs.jmedchem.7b01113	Muscarinic acetylcholine receptor M3	7
26225816	10.1021/acs.jmedchem.5b00904	Neuronal acetylcholine receptor; alpha4/beta2	6
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
24856614	10.1021/jm500556a	Muscarinic acetylcholine receptor M1	5
15050613	10.1016/j.bmcl.2003.09.105	Unchecked	5
25478907	10.1021/jm500860w	Muscarinic acetylcholine receptor M1	5
6502594	10.1021/jm00378a020	ADMET	4
18989912	10.1021/jm701625v	Neuronal acetylcholine receptor; alpha3/beta4	4
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
16033252	10.1021/jm040219e	Unchecked	4
10447956	10.1021/jm991004l	Rattus norvegicus	4
-	10.1016/S0960-894X(96)00429-5	Acetylcholine receptor subunit delta	4
22677319	10.1016/j.bmcl.2012.05.048	Muscarinic acetylcholine receptor M1	4
17722904	10.1021/jm070574f	Neuronal acetylcholine receptor subunit alpha-7	4

Data from ChEMBL 36 via Core Engine