Showing Compound Acetylcholine(1+) (FDB012191)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:02 UTC

Update date

2019-11-26 03:06:21 UTC

Primary ID

FDB012191

Secondary Accession Numbers

FDB004643

Chemical Information

FooDB Name

Acetylcholine(1+)

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.

CAS Number

51-84-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
ACh	ChEBI
Azetylcholin	ChEBI
Choline acetate	ChEBI
O-Acetylcholine	ChEBI
Choline acetic acid	Generator
Acetylcholine iodide	HMDB
Acetylcholine perchlorate	HMDB
Acetylcholine sulfate (1:1)	HMDB
Bromoacetylcholine	HMDB
Cusi, acetilcolina	HMDB
Iodide, acetylcholine	HMDB
2-(Acetyloxy)-N,N,N-trimethylethanaminium	HMDB
Acetilcolina cusi	HMDB
Acetylcholine fluoride	HMDB
Acetylcholine L tartrate	HMDB
Acetylcholine picrate	HMDB
Chloroacetylcholine	HMDB
Miochol	HMDB
Perchlorate, acetylcholine	HMDB
Acetylcholine L-tartrate	HMDB
Acetylcholine picrate (1:1)	HMDB
Hydroxide, acetylcholine	HMDB
Acetylcholine bromide	HMDB
Acetylcholine chloride	HMDB
Acetylcholine hydroxide	HMDB
Bromide, acetylcholine	HMDB
Fluoride, acetylcholine	HMDB
L-Tartrate, acetylcholine	HMDB
Acetyl choline ion	HMDB
Acetylcholine cation	HMDB
Acetylcholinium: acetyl-choline	HMDB
Choline acetate (ester)	HMDB
Bournonville brand OF acetylcholine chloride	HMDB
Iolab brand OF acetylcholine chloride	HMDB
Alcon brand OF acetylcholine chloride	HMDB
Ciba vision brand OF acetylcholine chloride	HMDB
Acetylcholine	MeSH, HMDB
2-Acetyloxy-N,N,N-trimethylethanaminium, 9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-4.2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.35 m³·mol⁻¹	ChemAxon
Polarizability	16.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H16NO2

IUPAC name

[2-(acetyloxy)ethyl]trimethylazanium

InChI Identifier

InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1

InChI Key

OIPILFWXSMYKGL-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

146.2074

Monoisotopic Molecular Weight

146.118103761

Classification

Description

Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Acyl cholines

Alternative Parents

Substituents

Acyl choline
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:15355 )
acylcholine (CHEBI:15355 )
Acetylcholine (C01996 )
a small molecule (ACETYLCHOLINE )

Ontology

Physiological effect

Health effect:

Health condition:

Multi-infarct dementia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Microbe:

Lactobacillus

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 57.50%; H 11.03%; N 9.58%; O 21.89%	DFC
Melting Point	148 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Acetylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4r-9100000000-bf8d3f373f038db1a310	Spectrum
Predicted GC-MS	Acetylcholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000j-9600000000-ec60451904fda7dde556	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000l-9000000000-2ea4c086c3ab458a1d7c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-98d5a70eed75a0945da4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-1900000000-2da10e016ac539b6e981	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-7efaaa08a6c43d816358	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-9000000000-eb7d66198d7674cbbd2a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000l-9000000000-41b87d773c58129802e9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-9e8e66250f2cf34a2046	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-f7fe18f2371596dc7333	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000j-9800000000-b0f987ebcb0179a2c5ab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-9000000000-1be58612df9c1eef1282	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-1900000000-2da10e016ac539b6e981	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-7efaaa08a6c43d816358	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-eb7d66198d7674cbbd2a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000l-9000000000-41b87d773c58129802e9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-9ac44e29bdfbddf1b90d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-f7fe18f2371596dc7333	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000j-9800000000-b0f987ebcb0179a2c5ab	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000j-9400000000-8a3a0b77e93715b85ed4	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum