Preferred Name

choline

Synonyms

Choline

CHOLINE ION

N-trimethylethanolamine

2-Hydroxy-N

N

Cholinum

Choline cation

N,N,N-trimethylethanol-ammonium

(2-Hydroxyethyl)trimethylammonium

N-trimethylethanaminium

choline

Bilineurine

2-hydroxy-N,N,N-trimethylethanaminium

Choline ion

trimethylethanolamine

Definitions

A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. 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

ID

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

charge

+1

createdDate

May 12, 2010

database_cross_reference

KEGG:D07690

Reaxys:1736748

PMID:22770225

PMID:22961562

PMID:18230680

PMID:18204095

PMID:17344490

PMID:7590654

PMID:18786517

PDBeChem:CHT

PMID:10930630

PMID:17087106

YMDB:YMDB00227

CAS:62-49-7

PMID:9517478

PMID:23637565

Wikipedia:Choline

PMID:6420466

KNApSAcK:C00007298

PMID:18786520

PMID:17283071

DrugBank:DB00122

KEGG:C00114

PMID:19246089

MetaCyc:CHOLINE

PMID:23733158

Beilstein:1736748

PMID:23095202

ECMDB:ECMDB00097

Drug_Central:3097

Gmelin:324597

HMDB:HMDB0000097

PMID:12946691

PMID:20038853

PMID:23616508

PMID:14972364

PMID:16210714

PMID:12826235

PMID:20446114

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 role

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

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

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

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

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

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

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

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

has_alternative_id

CHEBI:13985

CHEBI:23212

CHEBI:3665

CHEBI:41524

has_exact_synonym

Choline

choline

2-hydroxy-N,N,N-trimethylethanaminium

has_obo_namespace

chebi_ontology

has_related_synonym

CHOLINE ION

N-trimethylethanolamine

N,N,N-trimethylethanol-ammonium

Bilineurine

trimethylethanolamine

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

104.108

notation

CHEBI:15354

prefLabel

choline

smiles

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

synonym

2-Hydroxy-N

N

Cholinum

Choline cation

(2-Hydroxyethyl)trimethylammonium

N-trimethylethanaminium

Choline ion

textual definition

A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function.

subClassOf

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

Delete Subject Author Type Created
No notes to display
Create New Mapping

Delete Mapping To Ontology Source
http://purl.bioontology.org/ontology/CSP/0663-0420 CRISP LOOM
http://purl.jp/bio/4/id/200906097406502953 IOBC LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D02.092.877.883.333 RH-MESH LOOM
http://purl.bioontology.org/ontology/MESH/D002794 MESH LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D002794 RH-MESH LOOM
http://purl.bioontology.org/ontology/RCD/Ub08Y RCD LOOM
http://id.loc.gov/authorities/subjects/sh85024656 FAST-TOPICAL LOOM
http://www.semanticweb.org/ADMO#Choline ADMO LOOM
http://stirdf.jst.go.jp/id/200907025661687641 IOBC LOOM
http://data.bnf.fr/ark:/12148/cb122695833 FAST-TOPICAL LOOM
http://www.semanticweb.org/tome/ontologies/2015/7/Richfields#choline ISO-FOOD LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D02.092.063.291.211 RH-MESH LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D02.675.276.232 RH-MESH LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D02.033.100.291.211 RH-MESH LOOM
http://purl.bioontology.org/ontology/RXNORM/2449 RXNORM LOOM
http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C61674 NCIT LOOM
http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C61674 NCIT LOOM
http://purl.bioontology.org/ontology/SNOMEDCT/65123005 SNOMEDCT LOOM
http://purl.bioontology.org/ontology/NDFRT/N0000146071 NDFRT LOOM
http://purl.bioontology.org/ontology/VANDF/4017699 VANDF LOOM
http://doe-generated-ontology.com/OntoAD#C0008405 ONTOAD LOOM
http://purl.obolibrary.org/obo/dinto_DB00122 DINTO LOOM
http://ontology.apa.org/apaonto/termsonlyOUT%20(5).owl#Choline APANEUROCLUSTER LOOM
http://ontology.apa.org/apaonto/termsonlyOUT%20(5).owl#Choline APAONTO LOOM
http://www.bioontology.org/pma.owl#PMA_1559 PMA LOOM
http://www.projecthalo.com/aura#Choline AURA LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 BIOMODELS LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 BIOMODELS SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 CHEBI LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 CHEBI SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 OCMR LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 OCMR SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 GO-PLUS LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 GO-PLUS SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 GO-PLUS LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 GO-PLUS SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 EFO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 EFO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 DRON LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 DRON SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 UPHENO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 UPHENO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 FYPO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 CHEBI LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 CHEBI SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 HINO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 HINO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 EFO LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 EFO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_15354 ONSTR LOOM
http://purl.obolibrary.org/obo/CHEBI_15354 ONSTR SAME_URI
http://purl.bioontology.org/ontology/SNMI/F-61620 SNMI LOOM
http://www.co-ode.org/ontologies/galen#Choline GALEN LOOM