Metabolite Card

Formula: C7H16NO2 (146.1181)
SMILES: CC(=O)OCC[N+](C)(C)C

Synonyms [en]

acetylcholine; O-Acetylcholine; Ach; Acetylcholine Chloride; Azetylcholin; Choline acetate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Acetylcholine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000005786). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID:17284361, 17011181, 15556286). Acetylcholine has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID:24621061).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 14047-05-3
  • CAS Registry Number: 14586-35-7
  • CAS Registry Number: 51-84-3
  • CAS Registry Number: 60-31-1
  • PubChem: 187
  • ChEBI: ChEBI:15355
  • HMDB: HMDB0000895
  • KEGG: C01996
  • BioCyc: ACETYLCHOLINE
  • NCBI MeSH: Acetylcholine
  • Wikipedia: Acetylcholine
  • DrugBank: DB03128
  • RefMet: RM0041817
  • MoNA: BAF_UVA_POS000623
  • MoNA: CCMSLIB00000578035
  • MoNA: HMDB0000895_ms_ms_1262
  • MoNA: HMDB0000895_ms_ms_1263
  • MoNA: HMDB0000895_ms_ms_1264
  • MoNA: KO002178
  • MoNA: KO002179
  • MoNA: KO002180
  • MoNA: KO002181
  • MoNA: KO002182
  • MoNA: MoNA010202
  • MoNA: MoNA010203
  • MoNA: MoNA010204
  • MoNA: MoNA010205
  • MoNA: MoNA010206
  • MoNA: MoNA010207
  • MoNA: MoNA016620
  • MoNA: MoNA016653
  • MoNA: MoNA032256
  • MoNA: MoNA032257
  • MoNA: MoNA032260
  • MoNA: MoNA036956
  • MoNA: MoNA036958
  • MoNA: MoNA036959
  • MoNA: MoNA037223
  • MoNA: MoNA038604
  • MoNA: MoNA_0006685
  • MoNA: MoNA_0006686
  • MoNA: MoNA_0007448
  • MoNA: MoNA_0007449
  • MoNA: MoNA_0007450
  • MoNA: MoNA_0007451
  • MoNA: MoNA_0007452
  • MoNA: MoNA_0007453
  • MoNA: PB000347
  • MoNA: PR100098
  • MoNA: PR100099
  • MoNA: PS016301
  • MoNA: PS016302
  • MoNA: PS016303
  • MoNA: PS016304
  • MoNA: PS016305
  • MoNA: PS016306
  • MoNA: PT101630
  • MoNA: PT101633
  • Coconut NaturalProduct: CNP0584438.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01023 2.3.1.6 acetyl-CoA:choline O-acetyltransferase
KEGG:R01026 3.1.1.7 acetylcholine aectylhydrolase
Rhea:RHEA:17562 3.1.1.7 acetylcholine + H2O => choline + acetate + H+
Rhea:RHEA:17563 3.1.1.7 choline + acetate + H+ => acetylcholine + H2O
Rhea:RHEA:17564 3.1.1.7 acetylcholine + H2O <=> choline + acetate + H+
Rhea:RHEA:18822 2.3.1.6 choline + acetyl-CoA => acetylcholine + CoA
Rhea:RHEA:18823 2.3.1.6 acetylcholine + CoA => choline + acetyl-CoA
Rhea:RHEA:18824 2.3.1.6 choline + acetyl-CoA <=> acetylcholine + CoA
Rhea:RHEA:72892 acetylcholine(out) + 2 H+(in) => acetylcholine(in) + 2 H+(out)
Rhea:RHEA:72893 acetylcholine(in) + 2 H+(out) => acetylcholine(out) + 2 H+(in)
Rhea:RHEA:72894 acetylcholine(out) + 2 H+(in) <=> acetylcholine(in) + 2 H+(out)
Rhea:RHEA:74664 acetylcholine(in) => acetylcholine(out)
Rhea:RHEA:74665 acetylcholine(out) => acetylcholine(in)
Rhea:RHEA:74666 acetylcholine(in) <=> acetylcholine(out)
BioCyc:ACETYLCHOLINESTERASE-RXN 3.1.1.7 WATER + ACETYLCHOLINE --> PROTON + ACET + CHOLINE
BioCyc:ACH3-RXN ACETYLCHOLINE --> ACETYLCHOLINE
BioCyc:CHOLINE-O-ACETYLTRANSFERASE-RXN 2.3.1.6 CHOLINE + ACETYL-COA<=>ACETYLCHOLINE + CO-A
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Organism Source

Taxonomy Source

  1. Aesculus turbinata [ncbi taxid: 83375]
  2. Alnus alnobetula [ncbi taxid: 38784]
  3. Alternanthera pungens [ncbi taxid: 240021]
  4. Apis cerana [ncbi taxid: 7461]
  5. Argyreia speciosa [ncbi taxid: ]
  6. Artocarpus styracifolius [ncbi taxid: 1009334]
  7. Capsella bursa [ncbi taxid: ]
  8. Capsella bursa-pastoris [ncbi taxid: 3719]
  9. Chondodendron toxicoferum [ncbi taxid: ]
  10. Citrus aurantium [ncbi taxid: ]
  11. Claviceps purpurea [ncbi taxid: 5111]
  12. Crataegus pinnatifida [ncbi taxid: 510735]
  13. Dacrydium intermedium [ncbi taxid: ]
  14. Dickeya chrysanthemi [ncbi taxid: 556]
  15. Diospyros kaki [ncbi taxid: 35925]
  16. Dorstenia mannii [ncbi taxid: 194258]
  17. Forsythia giraldiana [ncbi taxid: 205689]
  18. Homo sapiens [ncbi taxid: 9606]
  19. Krameria parvifolia [ncbi taxid: ]
  20. Laurencia nidifica [ncbi taxid: 689809]
  21. Lecanora coniza [ncbi taxid: ]
  22. Moringa oleifera [ncbi taxid: 3735]
  23. Mus musculus [ncbi taxid: 10090]
  24. Phyllidiella pustulosa [ncbi taxid: 154616]
  25. Solanum nigrum [ncbi taxid: 4112]
  26. Streptomyces griseolus [ncbi taxid: 1909]
  27. Swertia chinensis [ncbi taxid: 149060]
  28. Ursus arctos [ncbi taxid: 9644]
  29. Ursus thibetanus [ncbi taxid: 9642]
  30. Urtica dioica L. [ncbi taxid: ]
  31. Urtica urens L. [ncbi taxid: ]
  32. Vernonia profuga [ncbi taxid: 434704]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-3301 sinapate ester biosynthesis
PlantCyc:PLANT_PWY-3301 sinapate ester biosynthesis
Reactome:R-HSA-9659379 Sensory processing of sound
Reactome:R-HSA-9709957 Sensory Perception
Reactome:R-HSA-9667769 Acetylcholine inhibits contraction of outer hair cells
Reactome:R-HSA-9662361 Sensory processing of sound by outer hair cells of the cochlea
Reactome:R-BTA-381771 Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1)
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-556833 Metabolism of lipids
Reactome:R-BTA-112310 Neurotransmitter release cycle
Reactome:R-BTA-622327 Postsynaptic nicotinic acetylcholine receptors
Reactome:R-BTA-500792 GPCR ligand binding
Reactome:R-BTA-375280 Amine ligand-binding receptors
Reactome:R-BTA-418594 G alpha (i) signalling events
Reactome:R-CEL-112315 Transmission across Chemical Synapses
Reactome:R-CEL-181431 Acetylcholine binding and downstream events
Reactome:R-CEL-629587 Highly sodium permeable postsynaptic acetylcholine nicotinic receptors
Reactome:R-CEL-373076 Class A/1 (Rhodopsin-like receptors)
Reactome:R-CEL-388396 GPCR downstream signalling
Reactome:R-CFA-381771 Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1)
View All Pathways