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Showing Compound Choline (FDB000710)

Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2024-11-29 22:26:10 UTC
Primary IDFDB000710
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCholine
DescriptionCholine, also known as bilineurine, is an organic compound containing a N, N, N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline is 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. In plants, the first step in de novo biosynthesis of choline involves the decarboxylation of serine into ethanolamine, which is catalyzed by a serine decarboxylase. The synthesis of choline from ethanolamine involves three consecutive N-methylation steps catalyzed by a methyl transferase. In terms of human health, choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to fatty liver disease and general liver damage. This arises from the lack of VLDL , which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.
CAS Number62-49-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
BilineurineChEBI
CHOLINE ionChEBI
N,N,N-Trimethylethanol-ammoniumChEBI
N-TrimethylethanolamineChEBI
TrimethylethanolamineChEBI
Choline cationKegg
(2-Hydroxyethyl)trimethyl ammoniumHMDB
(2-Hydroxyethyl)trimethylammoniumHMDB
(beta-Hydroxyethyl)trimethylammoniumHMDB
2-Hydroxy-N,N,N-trimethyl-ethanaminiumHMDB
2-Hydroxy-N,N,N-trimethylethanaminiumHMDB
BiocolinaHMDB
BiocolineHMDB
CholinumHMDB
HepacholineHMDB
HormoclineHMDB
LipotrilHMDB
N,N,N-TrimethylethanolammoniumHMDB
NeocolinaHMDB
ParesanHMDB
Choline O-sulfateHMDB
Citrate, cholineHMDB
FagineHMDB
Hydroxide, cholineHMDB
VidineHMDB
BursineHMDB
Chloride, cholineHMDB
Choline chlorideHMDB
Choline citrateHMDB
Bitartrate, cholineHMDB
Choline bitartrateHMDB
Choline hydroxideHMDB
Choline O sulfateHMDB
O-Sulfate, cholineHMDB
2-Hydroxy-N,N,N-trimethylethanaminium(1+), 9CIdb_source
2-Hydroxyethyl-trimethylazaniumbiospider
Amanitin?db_source
Arachinedb_source
Araquinedb_source
Choline (8CI)biospider
Choline ionbiospider
Ethanaminium, 2-hydroxy-N,N,N-trimethyl- (9CI)biospider
Sincalindb_source
Sinkalindb_source
Predicted Properties
PropertyValueSource
Water Solubility3.61 g/LALOGPS
logP-3.6ALOGPS
logP-4.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.19 m³·mol⁻¹ChemAxon
Polarizability12.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H14NO
IUPAC name(2-hydroxyethyl)trimethylazanium
InChI IdentifierInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChI KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
Isomeric SMILESC[N+](C)(C)CCO
Average Molecular Weight104.1708
Monoisotopic Molecular Weight104.107539075
Classification
Description Belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCholines
Alternative Parents
Substituents
  • Choline
  • Tetraalkylammonium salt
  • 1,2-aminoalcohol
  • Alkanolamine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Amine
  • Alcohol
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.65%; H 13.55%; N 13.45%; O 15.36%DFC
Melting Point302-303 oC (Chloride salt)
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge+1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9100000000-69389426dd865af031f9Spectrum
Predicted GC-MSCholine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-9300000000-ca1b0086d4882b00b395Spectrum
Predicted GC-MSCholine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCholine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-ea6f9c1150759c5be6c72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-1900000000-cadf16d18f093e9b19d62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bt9-9100000000-a2c328b7da5435b8e4672012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-6a7b57dbdf45607217222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-5900000000-87fdeef5275a74e783482012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0w29-5900000000-9b79cc5ff3b1ce17deb12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9200000000-fe62d5a4fbf492493d602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-3900000000-0b37e63e9c6b14a2e3972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-6a7b57dbdf45607217222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-5900000000-87fdeef5275a74e783482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-1900000000-391c1b7859a03e7761232017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-43b0f930ff04f7a48a592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9400000000-ab7cc75a8e0d3cc494492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-0b94edfd44e38b20b8d32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9100000000-a738404b52e2f1f6fec12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-c596e40769889223b3dd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-c6fab16d1790976560b52021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)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
ChemSpider ID299
ChEMBL IDCHEMBL920
KEGG Compound IDC00114
Pubchem Compound ID305
Pubchem Substance IDNot Available
ChEBI ID15354
Phenol-Explorer IDNot Available
DrugBank IDDB00122
HMDB IDHMDB00097
CRC / DFC (Dictionary of Food Compounds) IDBFT67-H:BFT67-H
EAFUS IDNot Available
Dr. Duke IDCHOLINE
BIGG ID33910
KNApSAcK IDC00007298
HET IDCHT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti-choreic52217 An agent that reduces involuntary movements, commonly used in managing neurological disorders such as Huntington's disease, Parkinson's disease, and tic disorders, by blocking excessive dopamine activity in the brain, thereby alleviating symptoms of chorea, athetosis, and dystonia.DUKE
Anti-cirrhotic52217 An agent that prevents or treats liver cirrhosis, reducing fibrosis and promoting liver health. It inhibits liver scarring, commonly used in managing liver diseases such as hepatitis and fatty liver disease.DUKE
Anti-cystinuricAn agent that reduces cystine stone formation in the kidneys, ureter, or bladder, used to manage cystinuria, a genetic disorder causing excessive cystine excretion.DUKE
Anti-dementia52217 An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti dyskineticAn agent that relieves or prevents dyskinesia, improving voluntary movement. It plays a biological role in regulating motor function, and has therapeutic applications in managing Parkinson's disease, Huntington's disease, and other movement disorders, reducing involuntary movements and improving motor control.DUKE
Anti homocysteine35222 An agent that reduces homocysteine levels, an amino acid linked to cardiovascular disease and neurological disorders. It plays a biological role in methionine metabolism and has therapeutic applications in preventing cardiovascular events, stroke, and dementia. Key medical uses include managing hyperhomocysteinemia, reducing cardiovascular risk, and treating conditions associated with elevated homocysteine levels.DUKE
Anti-manicAn agent that stabilizes mood by controlling symptoms of mania, used to manage bipolar disorder, reducing excessive excitement and impulsivity, and preventing manic episodes.DUKE
Anti nociceptive35470 An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.DUKE
Anti steatoticAn agent that prevents lipid accumulation in cells, reducing steatosis. It plays a biological role in maintaining cellular lipid homeostasis. Therapeutically, it has applications in managing fatty liver disease, obesity, and metabolic disorders, with key medical uses including treatment of non-alcoholic fatty liver disease (NAFLD) and steatohepatitis.DUKE
Cardiodepressant38070 An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.DUKE
CerebrotonicA personality type characterized by shyness, introspection, and emotional restraint, often linked to an ectomorphic physique. It has no direct biological role or therapeutic applications, but understanding cerebrotonic traits can inform approaches to anxiety, social anxiety, or introversion management, and may be relevant in counseling or psychotherapy.DUKE
Cholinergic38323 An agent that stimulates the parasympathetic nervous system by mimicking acetylcholine, enhancing muscle contraction, and regulating various bodily functions. Therapeutically, it treats conditions like glaucoma, myasthenia gravis, and Alzheimer's disease, improving muscle tone, cognition, and eye pressure.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
IleorelaxantAn agent that reduces the muscular action of the ileum, playing a biological role in regulating intestinal motility. Therapeutically, it is used to relieve abdominal cramps, diarrhea, and irritable bowel syndrome (IBS) symptoms, making it a key medical treatment for gastrointestinal disorders.DUKE
LipotropicA compound that facilitates fat breakdown and metabolism, playing a biological role in lipid utilization. Therapeutically, it's used to enhance weight loss and improve liver function. Key medical applications include treating fatty liver disease, obesity, and hyperlipidemia, making it a valuable agent in managing metabolic disorders.DUKE
MemorigenicAn agent that enhances memory and cognitive function, playing a biological role in neuroprotection and neuroplasticity. Therapeutically, it has applications in managing neurodegenerative diseases, such as Alzheimer's and dementia, and key medical uses include improving memory recall and learning capacity.DUKE
ParasympathomimeticA substance that stimulates the parasympathetic nervous system, mimicking acetylcholine by activating nicotinic or muscarinic receptors. Therapeutically, it's used to treat conditions like glaucoma, asthma, and gastrointestinal disorders, promoting smooth muscle contraction and glandular secretion, while also slowing heart rate.DUKE
Neurotransmitter25512 A chemical messenger that transmits signals between neurons, regulating various physiological and psychological processes. Therapeutically, neurotransmitter modulators are used to treat conditions such as depression, anxiety, and Parkinson's disease, by altering neurotransmitter levels or activity to restore balance and alleviate symptoms.CHEBI
Enzymes
NameGene NameUniProt ID
Choline O-acetyltransferaseCHATP28329
Phospholipase D2PLD2O14939
AcetylcholinesteraseACHEP22303
CholinesteraseBCHEP06276
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Choline/ethanolamine kinaseCHKBQ9Y259
Choline kinase alphaCHKAP35790
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Phospholipase D6PLD6Q8N2A8
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123 map00260
Methionine MetabolismSMP00033 map00270
Phospholipid BiosynthesisSMP00025 map00564
Metabolism and Physiological Effects of Trimethylamine N-oxide (TMAO)SMP0123192 Not Available
Metabolism and Physiological Effects of DimethylglycineSMP0124873 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).