Preferred Name

choline

Synonyms

2-hydroxy-N,N,N-trimethylethanaminium

Choline

choline

Bilineurine

N-trimethylethanolamine

CHOLINE ION

trimethylethanolamine

N,N,N-trimethylethanol-ammonium

(2-Hydroxyethyl)trimethylammonium

Choline cation

Choline ion

N

N-trimethylethanaminium

2-Hydroxy-N

Cholinum

Definitions

A basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. (PubChem) Pharmacology: This compound is needed for good nerve conduction throughout the CNS (central nervous system) as it is a precursor to acetylcholine (ACh). Choline is also needed for gallbladder regulation, liver function and lecithin (a key lipid) formation. Choline also aids in fat and cholesterol metabolism and prevents excessive fat build up in the liver. Choline has been used to mitigate the effects of Parkinsonism and tardive dyskinesia. Choline deficiencies may result in excessive build-up of fat in the liver, high blood pressure, gastric ulcers, kidney and liver dysfunction and stunted growth. Mechanism of action: Choline is a major part of the polar head group of phosphatidylcholine. Phosphatidylcholine's role in the maintenance of cell membrane integrity is vital to all of the basic biological processes: information flow, intracellular communication and bioenergetics. Inadequate choline intake would negatively affect all these processes. Choline is also a major part of another membrane phospholipid, sphingomyelin, also important for the maintenance of cell structure and function. It is noteworthy and not surprising that choline deficiency in cell culture causes apoptosis or programmed cell death. This appears to be due to abnormalities in cell membrane phosphatidylcholine content and an increase in ceramide, a precursor, as well as a metabolite, of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate Caspase, a type of enzyme that mediates apoptosis. Betaine or trimethylglycine is derived from choline via an oxidation reaction. Betaine is one of the factors that maintains low levels of homocysteine by resynthesizing L-methionine from homocysteine. Elevated homocysteine levels are a significant risk factor for atherosclerosis, as well as other cardiovascular and neurological disorders. Acetylcholine is one of the major neurotransmitters and requires choline for its synthesis. Adequate acetylcholine levels in the brain are believed to be protective against certain types of dementia, including Alzheimer's disease. Drug type: Approved. Nutraceutical. Small Molecule. Drug category: Dietary supplement. Lipotropic Agents. Micronutrient. Nootropic Agents A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function.

ID

http://purl.obolibrary.org/obo/CHEBI_15354

charge

+1

createdDate

May 12, 2010

database_cross_reference

DrugBank:DB00122

PMID:18786520

PMID:22961562

KEGG:D07690

ECMDB:ECMDB00097

PMID:20038853

PMID:20446114

KNApSAcK:C00007298

Wikipedia:Choline

PMID:16210714

PMID:14972364

PDBeChem:CHT

PMID:7590654

KEGG:C00114

HMDB:HMDB0000097

PMID:23733158

Reaxys:1736748

MetaCyc:CHOLINE

PMID:19246089

PMID:18204095

CAS:62-49-7

YMDB:YMDB00227

Beilstein:1736748

PMID:18786517

PMID:22770225

PMID:18230680

PMID:12826235

PMID:23616508

PMID:17344490

PMID:12946691

PMID:17087106

PMID:6420466

PMID:10930630

PMID:23637565

Gmelin:324597

PMID:17283071

PMID:23095202

Drug_Central:3097

PMID:9517478

definingCitation

http://www.drugbank.ca/drugs/DB00122

definition

A basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. (PubChem) Pharmacology: This compound is needed for good nerve conduction throughout the CNS (central nervous system) as it is a precursor to acetylcholine (ACh). Choline is also needed for gallbladder regulation, liver function and lecithin (a key lipid) formation. Choline also aids in fat and cholesterol metabolism and prevents excessive fat build up in the liver. Choline has been used to mitigate the effects of Parkinsonism and tardive dyskinesia. Choline deficiencies may result in excessive build-up of fat in the liver, high blood pressure, gastric ulcers, kidney and liver dysfunction and stunted growth. Mechanism of action: Choline is a major part of the polar head group of phosphatidylcholine. Phosphatidylcholine's role in the maintenance of cell membrane integrity is vital to all of the basic biological processes: information flow, intracellular communication and bioenergetics. Inadequate choline intake would negatively affect all these processes. Choline is also a major part of another membrane phospholipid, sphingomyelin, also important for the maintenance of cell structure and function. It is noteworthy and not surprising that choline deficiency in cell culture causes apoptosis or programmed cell death. This appears to be due to abnormalities in cell membrane phosphatidylcholine content and an increase in ceramide, a precursor, as well as a metabolite, of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate Caspase, a type of enzyme that mediates apoptosis. Betaine or trimethylglycine is derived from choline via an oxidation reaction. Betaine is one of the factors that maintains low levels of homocysteine by resynthesizing L-methionine from homocysteine. Elevated homocysteine levels are a significant risk factor for atherosclerosis, as well as other cardiovascular and neurological disorders. Acetylcholine is one of the major neurotransmitters and requires choline for its synthesis. Adequate acetylcholine levels in the brain are believed to be protective against certain types of dementia, including Alzheimer's disease. Drug type: Approved. Nutraceutical. Small Molecule. Drug category: Dietary supplement. Lipotropic Agents. Micronutrient. Nootropic Agents

formula

C5H14NO

has exact synonym

2-hydroxy-N,N,N-trimethylethanaminium

Choline

choline

has role

http://purl.obolibrary.org/obo/CHEBI_25512

http://purl.obolibrary.org/obo/CHEBI_76924

http://purl.obolibrary.org/obo/CHEBI_83056

http://purl.obolibrary.org/obo/CHEBI_33284

http://purl.obolibrary.org/obo/CHEBI_75772

http://purl.obolibrary.org/obo/CHEBI_77746

http://purl.obolibrary.org/obo/CHEBI_50904

http://purl.obolibrary.org/obo/CHEBI_75771

http://purl.obolibrary.org/obo/CHEBI_76971

has_alternative_id

CHEBI:13985

CHEBI:23212

CHEBI:41524

CHEBI:3665

has_obo_namespace

chebi_ontology

has_related_synonym

Bilineurine

N-trimethylethanolamine

CHOLINE ION

trimethylethanolamine

N,N,N-trimethylethanol-ammonium

id

CHEBI:15354

in_subset

http://purl.obolibrary.org/obo/chebi#3_STAR

inchi

InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1

inchikey

OEYIOHPDSNJKLS-UHFFFAOYSA-N

label

choline

mass

104.17080

monoisotopicmass

104.10699

notation

CHEBI:15354

prefLabel

choline

smiles

C[N+](C)(C)CCO

synonym

(2-Hydroxyethyl)trimethylammonium

Choline cation

Choline ion

N

N-trimethylethanaminium

2-Hydroxy-N

Cholinum

subClassOf

http://purl.obolibrary.org/obo/CHEBI_23217

http://purl.obolibrary.org/obo/BFO_0000004

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Delete Mapping To Ontology Source
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