Acetylcholine
PubChem CID: 187
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| Compound Synonyms | acetylcholine, Choline acetate, O-Acetylcholine, 51-84-3, (2-Acetoxyethyl)trimethylammonium, Acetyl choline ion, Acetylcholinum, Choline acetate (ester), Acetyl choline cation, 2-(Acetyloxy)-N,N,N-trimethylethanaminium, Ach, Azetylcholin, 2-acetyloxyethyl(trimethyl)azanium, ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, Acetylcholine cation, CHEBI:15355, BRN 1764436, UNII-N9YNS0M02X, EINECS 200-128-9, N9YNS0M02X, CHEMBL667, (2-Acetoxyethyl)trimetilammonium, DTXSID8075334, 4-04-00-01446 (Beilstein Handbook Reference), [2-(acetyloxy)ethyl]trimethylazanium, 2-acetyloxy-N,N,N-trimethylethanaminium, 2-acetyloxyethyl-trimethylazanium, ACETYLCHOLINE (USP IMPURITY), ACETYLCHOLINE [USP IMPURITY], [3H]acetylcholine, 14047-05-3, NCGC00018123-05, 2rin, 3rqw, (14C)Acetylcholine, (14C)-Acetylcholine, Spectrum_000022, 2ha4, 2xz5, starbld0009701, Spectrum2_001258, Spectrum3_000286, Spectrum4_000136, Spectrum5_000762, 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, HMS2089A14, 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, 2-Acetoxy-N,N,N-trimethylethan-1-aminium, SBI-0051271.P003, CS-0453239, NS00002053, ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl, C01996, AB00053790-25, AB00053790_26, AB00053790_27, L000783, Q180623, BRD-K82381502-003-23-1, BRD-K82381502-003-24-9, 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, 200-128-9 |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 26.3 |
| Hydrogen Bond Donor Count | 0.0 |
| Pfizer 3 75 Rule | False |
| Np Classifier Class | Wax monoesters |
| Deep Smiles | CC=O)OCC[N+]C)C)C |
| Heavy Atom Count | 10.0 |
| Pathway Kegg Map Id | map00564 |
| Classyfire Class | Organonitrogen compounds |
| Description | Occurs in Capsella bursa-pastoris (shepherd's purse) 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 is an ester of acetic acid and choline with chemical formula CH3COOCH2CH2N+(CH3)3. This structure is reflected in the systematic name, 2-acetoxy-N,N,N-trimethylethanaminium., In the PNS, acetylcholine activates muscles, and is a major neurotransmitter in the autonomic nervous system., In the peripheral nervous system, acetylcholine activates muscles, and is a major neurotransmitter in the autonomic nervous system. When acetylcholine binds to acetylcholine receptors on skeletal muscle fibers, it opens ligand gated sodium channels in the cell membrane. Sodium ions then enter the muscle cell, stimulating muscle contraction. Acetylcholine, while inducing contraction of skeletal muscles, instead inhibits contraction in cardiac muscle fibers. This distinction is attributed to differences in receptor structure between skeletal and cardiac fibers., The chemical compound acetylcholine (often abbreviated ACh) is a neurotransmitter in both the peripheral nervous system (PNS) and central nervous system (CNS) in many organisms including humans. Acetylcholine is one of many neurotransmitters in the autonomic nervous system (ANS) and the only neurotransmitter used in the motor division of the somatic nervous system. (Sensory neurons use glutamate and various peptides at their synapses.) Acetylcholine is also the principal neurotransmitter in all autonomic ganglia. Acetylcholine(1+) is found in herbs and spices and fruits. |
| Classyfire Subclass | Quaternary ammonium salts |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 115.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | P28329, P22303, P06276 |
| Uniprot Id | P28329, P22303, P06276, P02718, P43681, P36544, P32297, P12390, Q05941, P12392, P11229, P08912, P25101, Q8VH26, P49582, P10980, P08172, P20309, P08173, P09482, P58154, P08482, P08485, Q16637, Q9UBT6, n.a., Q9Z0E8, Q63089, H6TY12, O95342, Q8N539, P0DTD1 |
| Iupac Name | 2-acetyloxyethyl(trimethyl)azanium |
| Prediction Hob | 0.0 |
| Class | Quaternary ammonium salts |
| Veber Rule | True |
| Classyfire Superclass | Organic nitrogen compounds |
| Target Id | NPT410, NPT262, NPT266, NPT263, NPT264, NPT265, NPT93 |
| Xlogp | 0.2 |
| Superclass | Organonitrogen compounds |
| Subclass | Cholines |
| Gsk 4 400 Rule | True |
| Molecular Formula | C7H16NO2+ |
| Prediction Swissadme | 0.0 |
| Inchi Key | OIPILFWXSMYKGL-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.8571428571428571 |
| Logs | 0.135 |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Logd | -1.283 |
| Synonyms | 2-Acetyloxy-N,N,N-trimethylethanaminium, 9CI, Acetyl choline ion, Acetylcholine, Acetylcholine cation, Acetylcholinium: acetyl-choline, ACh, Azetylcholin, Choline acetate, Choline acetate (ester), Choline acetic acid, O-Acetylcholine, Acetylcholine iodide, Acetylcholine perchlorate, Acetylcholine sulfate (1:1), Bromoacetylcholine, Cusi, acetilcolina, Iodide, acetylcholine, 2-(Acetyloxy)-N,N,N-trimethylethanaminium, Acetilcolina cusi, Acetylcholine fluoride, Acetylcholine L tartrate, Acetylcholine picrate, Chloroacetylcholine, Miochol, Perchlorate, acetylcholine, Acetylcholine L-tartrate, Acetylcholine picrate (1:1), Hydroxide, acetylcholine, Acetylcholine bromide, Acetylcholine chloride, Acetylcholine hydroxide, Bromide, acetylcholine, Fluoride, acetylcholine, L-Tartrate, acetylcholine, Bournonville brand OF acetylcholine chloride, Iolab brand OF acetylcholine chloride, Alcon brand OF acetylcholine chloride, Ciba vision brand OF acetylcholine chloride, acetyl-choline, acetylcholine, choline, acetyl |
| Substituent Name | Acyl choline, Acetate salt, Carboxylic acid ester, Monocarboxylic acid or derivatives, Ether, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Amine, Organic cation, Aliphatic acyclic compound |
| Esol Class | Highly soluble |
| Functional Groups | COC(C)=O, C[N+](C)(C)C |
| Compound Name | Acetylcholine |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 146.118 |
| Formal Charge | 1.0 |
| Monoisotopic Mass | 146.118 |
| Hydrogen Bond Acceptor Count | 2.0 |
| Molecular Weight | 146.21 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | 2.2264980000000003 |
| Inchi | InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1 |
| Smiles | CC(=O)OCC[N+](C)(C)C |
| Nring | 0.0 |
| Np Classifier Biosynthetic Pathway | Fatty acids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Acyl cholines |
| Np Classifier Superclass | Fatty esters |
- 1. Outgoing r'ship
FOUND_INto/from Aesculus Turbinata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Albizia Julibrissin (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/16658209 - 3. Outgoing r'ship
FOUND_INto/from Alnus Alnobetula (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Argyreia Speciosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Artocarpus Heterophyllus (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 6. Outgoing r'ship
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FOUND_INto/from Asystasia Gangetica (Plant) Rel Props:Reference:ISBN:9788172360481 - 8. Outgoing r'ship
FOUND_INto/from Capsella Bursa-Pastoris (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Citrus Aurantium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Coriandrum Sativum (Plant) Rel Props:Reference:ISBN:9780387706375 - 11. Outgoing r'ship
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