choline (CHEBI:15354)

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ChEBI Name	choline

ChEBI ID	CHEBI:15354

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

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41524, CHEBI:3665, CHEBI:13985, CHEBI:23212

Supplier Information	ChemicalBook:CB6705020, eMolecules:518145, eMolecules:883971, ZINC000006661227

Download	Molfile XML SDF

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Wikipedia	License
l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains. l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome. l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.
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Formula

C5H14NO

Net Charge

Average Mass

104.17080

Monoisotopic Mass

104.10699

InChI

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

InChIKey

OEYIOHPDSNJKLS-UHFFFAOYSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Arabidopsis thaliana (NCBI:txid3702)	See: DOI
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). nutrient A nutrient is a food component that an organism uses to survive and grow. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. allergen A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.

ChEBI Ontology
Outgoing	choline (CHEBI:15354) has role Daphnia magna metabolite (CHEBI:83056) choline (CHEBI:15354) has role Escherichia coli metabolite (CHEBI:76971) choline (CHEBI:15354) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) choline (CHEBI:15354) has role allergen (CHEBI:50904) choline (CHEBI:15354) has role human metabolite (CHEBI:77746) choline (CHEBI:15354) has role mouse metabolite (CHEBI:75771) choline (CHEBI:15354) has role neurotransmitter (CHEBI:25512) choline (CHEBI:15354) has role nutrient (CHEBI:33284) choline (CHEBI:15354) has role plant metabolite (CHEBI:76924) choline (CHEBI:15354) is a cholines (CHEBI:23217)

Incoming	choline ester (CHEBI:23213) has functional parent choline (CHEBI:15354) choline chloride (CHEBI:133341) has part choline (CHEBI:15354)

IUPAC Name

2-hydroxy-N,N,N-trimethylethanaminium

Synonyms	Sources
Bilineurine	KEGG COMPOUND
Choline	KEGG COMPOUND
choline	UniProt
CHOLINE ION	PDBeChem
N,N,N-trimethylethanol-ammonium	ChEBI
N-trimethylethanolamine	ChEBI
trimethylethanolamine	ChEBI

Last Modified

04 March 2019

General Comment
2011-04-27	A metabolite of phosphatidylcholine.