Acetylcholine

Details

• Internal ID: 2dc8cbc0-c1ea-4afa-a372-56430f12fab3
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Quaternary ammonium salts > Cholines > Acyl cholines
• IUPAC Name: 2-acetyloxyethyl(trimethyl)azanium
• SMILES (Canonical): CC(=O)OCC[N+](C)(C)C
• SMILES (Isomeric): 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
• Popularity: 68,503 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₆NO₂+
• Molecular Weight: 146.21 g/mol
• Exact Mass: 146.118103753 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Choline acetate
• O-Acetylcholine
• 51-84-3
• (2-Acetoxyethyl)trimethylammonium
• Acetyl choline ion
• Acetylcholinum
• Choline acetate (ester)
• Acetyl choline cation
• Ach
• Azetylcholin
• 2-(Acetyloxy)-N,N,N-trimethylethanaminium
• Acetylcholine cation
• 2-acetyloxyethyl(trimethyl)azanium
• ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-
• CHEBI:15355
• BRN 1764436
• COL Acetate
• UNII-N9YNS0M02X
• EINECS 200-128-9
• [3H]acetylcholine
• N9YNS0M02X
• Bromoacetylcholine
• [2-(acetyloxy)ethyl]trimethylazanium
• CHEMBL667
• C7H16NO2
• (2-Acetoxyethyl)trimetilammonium
• DTXSID8075334
• 4-04-00-01446 (Beilstein Handbook Reference)
• 2-acetyloxy-N,N,N-trimethylethanaminium
• 2-acetyloxyethyl-trimethylazanium
• ACETYLCHOLINE (USP IMPURITY)
• ACETYLCHOLINE [USP IMPURITY]
• NCGC00018123-05
• 2rin
• 3rqw
• (14C)Acetylcholine
• (14C)-Acetylcholine
• Spectrum_000022
• 2ha4
• 2xz5
• starbld0009701
• Spectrum2_001258
• Spectrum3_000286
• Spectrum4_000136
• Spectrum5_000762
• D04GON
• D0Q9HF
• Epitope ID:176773
• cid_6060
• SCHEMBL3216
• ACETYLCHOLINE [VANDF]
• BSPBio_001792
• GTPL294
• KBioGR_000552
• KBioSS_000382
• DivK1c_000686
• SPBio_001196
• ACETYLCHOLINE [WHO-DD]
• Acetylcholinium: acetyl-Choline
• GTPL8593
• DTXCID6040951
• BDBM10759
• KBio1_000686
• KBio2_000382
• KBio2_002950
• KBio2_005518
• KBio3_001292
• NINDS_000686
• OIPILFWXSMYKGL-UHFFFAOYSA-N
• HMS2089A14
• C7-H16-N-O2
• NSC800293
• AKOS040734806
• DB03128
• NSC-800293
• IDI1_000686
• 2-acetoxyethyl(trimethyl)ammonium;bromide
• NCGC00018123-01
• NCGC00018123-02
• NCGC00018123-03
• NCGC00018123-04
• NCGC00021161-03
• NCGC00021161-04
• NCGC00163215-01
• LS-53168
• 2-Acetoxy-N,N,N-trimethylethan-1-aminium
• SBI-0051271.P003
• 2-acetoxyethyl(trimethyl)ammonium;perchlorate
• CS-0453239
• FT-0689161
• ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl
• C01996
• AB00053790-25
• AB00053790_26
• AB00053790_27
• L000783
• Q180623
• Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl- (9CI)
• 2-(Acetyloxy)-N,N,N-trimethylethanaminium labeled with carbon-14
• Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, labeled with carbon-14
• InChI=1/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+
• 14047-05-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9623	96.23%
Caco-2	+	0.7936	79.36%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.4367	43.67%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9696	96.96%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9118	91.18%
P-glycoprotein inhibitior	-	0.9818	98.18%
P-glycoprotein substrate	-	0.9746	97.46%
CYP3A4 substrate	-	0.6389	63.89%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8314	83.14%
CYP3A4 inhibition	-	0.9689	96.89%
CYP2C9 inhibition	-	0.9611	96.11%
CYP2C19 inhibition	-	0.9565	95.65%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.8913	89.13%
CYP2C8 inhibition	-	0.9468	94.68%
CYP inhibitory promiscuity	-	0.9839	98.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6000	60.00%
Carcinogenicity (trinary)	Non-required	0.6261	62.61%
Eye corrosion	+	0.8390	83.90%
Eye irritation	+	0.9935	99.35%
Skin irritation	+	0.5169	51.69%
Skin corrosion	+	0.7453	74.53%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7565	75.65%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	1.0000	100.00%
skin sensitisation	-	0.7874	78.74%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.6719	67.19%
Acute Oral Toxicity (c)	III	0.5856	58.56%
Estrogen receptor binding	-	0.9393	93.93%
Androgen receptor binding	-	0.8347	83.47%
Thyroid receptor binding	-	0.9014	90.14%
Glucocorticoid receptor binding	-	0.9120	91.20%
Aromatase binding	-	0.8997	89.97%
PPAR gamma	-	0.9295	92.95%
Honey bee toxicity	-	0.9700	97.00%
Biodegradation	+	0.9000	90.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.9084	90.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	1.1 nM; 25.9 nM; 371.54 nM; 1.1 nM	EC50; EC50; EC50; EC50	PMID: 22677319; PMID: 26299349; PMID: 25478907; PMID: 20684563
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	220 nM; 7 nM; 220 nM	EC50; EC50; EC50	PMID: 22677319; via Super-PRED; PMID: 20684563
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	3.2 nM; 3.2 nM; 3.2 nM	EC50; EC50; EC50	via Super-PRED; PMID: 20684563; PMID: 22677319
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	10 nM; 10 nM; 10 nM	EC50; EC50; EC50	via Super-PRED; PMID: 20684563; PMID: 22677319
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	1.2 nM; 1.2 nM; 19.1 nM; 1.2 nM	EC50; EC50; EC50; EC50	via Super-PRED; PMID: 20684563; PMID: 26299349; PMID: 22677319
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	3981.07 nM; 230000 nM; 4000 nM; 180000 nM; 3981.07 nM; 69000 nM; 87000 nM; 155000 nM; 4000 nM; 83176.38 nM; 83000 nM	EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50	PMID: 17722904; PMID: 11212100; PMID: 17722904; PMID: 16033252; PMID: 17722904; PMID: 24900227; PMID: 24900227; PMID: 9435889; PMID: 17722904; PMID: 18989912; PMID: 18989912
CHEMBL3068	P32297	Neuronal acetylcholine receptor subunit alpha-3	19952.62 nM; 19000 nM; 144543.98 nM; 144000 nM	EC50; EC50; EC50; EC50	PMID: 19027295; PMID: 19027295; PMID: 18989912; PMID: 18989912
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.20%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.09%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.32%	96.95%

Plants that contains it

• Aesculus turbinata
• Alnus alnobetula
• Argyreia nervosa
• Artocarpus styracifolius
• Capsella bursa-pastoris
• Capsicum annuum
• Cnidoscolus texanus
• Crataegus pinnatifida
• Diospyros kaki
• Dorstenia mannii
• Forsythia giraldiana
• Krameria erecta
• Poa huecu
• Solanum nigrum
• Swertia diluta
• Vigna unguiculata

Cross-Links

• PubChem: 187
• NPASS: NPC1591
• ChEMBL: CHEMBL667
• LOTUS: LTS0185507
• wikiData: Q180623