Identification
NameCholine
Accession NumberDB00122  (NUTR00020)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

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]

Structure
Thumb
Synonyms
Bilineurine
Choline
Choline ion
N-trimethylethanolamine
N,N,N-trimethylethanol-ammonium
trimethylethanolamine
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Choline bitartrate6K2W7T9V6Y 87-67-2QWJSAWXRUVVRLH-LREBCSMRSA-MDetails
Choline salicylateKD510K1IQW 2016-36-6UDKCHVLMFQVBAA-UHFFFAOYSA-MDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Choline 250 mgTablet250 mgOralSwiss Herbal Remedies Ltd.1971-12-312004-09-03Canada
Choline 250mgTablet250 mgOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Choline 250mgTablet250 mgOralGeneral Nutrition Canada Inc.1997-04-182005-08-05Canada
Choline Bitartrate 100mg-tabTablet100 mgOralInternational Nutrition Ltd.1996-07-262001-08-17Canada
Choline Bitartrate 500 Mg - TabletTablet500 mgOralHealth Wise Nutrition Inc.1997-08-151998-08-25Canada
Choline Caps 350mgCapsule350 mgOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Choline Ctr Srt 400mgTablet, extended release400 mgOralBioenergy Inc.1979-12-311998-06-03Canada
Choline Tab 250mgTablet250 mgOralGahler Enterprises Ltd.1984-12-312000-08-01Canada
Choline Tab 250mgTablet250 mgOralVita Health Products Inc1976-12-311998-07-22Canada
Choline Tab 250mgTablet250 mgOralJamieson Laboratories Ltd1963-12-312000-09-08Canada
Cholinex Tab 200mgTablet200 mgOralTherapeutic Foods Co.1992-12-312004-07-22Canada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced 2000 CapsulesCapsuleOralBody Gold, A Division Of Pep Products, Inc.2000-01-012002-08-22Canada
AlertonicElixirOralOdan Laboratories Ltd1995-12-31Not applicableCanada
American Eagle Energizer Plus Vitamin Supplement DrinkLiquidOralP.S.W.C. Co., Inc.Not applicableNot applicableCanada
American Plus Energy & Vitamin DrinkLiquidOralP.S.W.C. Co., Inc.Not applicableNot applicableCanada
B 50 CapsulesCapsuleOralRheingold Food International Ltd.1987-12-312007-07-26Canada
B Complex 25mg Vitamin SupplementTabletOralGarden State Nutritionals1998-08-312000-06-07Canada
B Complex 50 Vitamin CapCapsuleOralBioforce Canada Inc.1994-12-311997-07-22Canada
B Complex 50+ CapletTabletOralHealth Wise Nutrition Inc.1994-12-312002-07-18Canada
B Compound 50mg TabTabletOralGahler Enterprises Ltd.1987-12-312009-09-28Canada
B-100 CapsCapsuleOralNow Foods2005-05-192008-07-11Canada
B-100 Hi Potency B Vitamins TabTabletOralNatrol, Inc.1994-12-312009-05-07Canada
B-100 Vitamin SupplementTablet, extended releaseOralGarden State Nutritionals1998-09-222000-06-07Canada
B-50 ComplexTabletOralVita Health Products Inc1977-12-312004-07-26Canada
B-50 Hi Potency B Vitamins TabTabletOralNatrol, Inc.1994-12-312006-09-26Canada
B-complexTabletOralEnrich International1999-11-112001-09-28Canada
B-complex 100TabletOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
B-complex 50TabletOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
B-complex TabTabletOralSantÉ Naturelle (Ag) LtÉe1988-12-312002-06-18Canada
B-complex With Vitamin C, Biotin, Folic AcidTabletOralWn Pharmaceuticals Ltd.2001-11-232009-09-28Canada
B-complex-50 TabTabletOralJr Carlson Labs Inc1998-10-252005-09-15Canada
B-plexTabletOralWn Pharmaceuticals Ltd.1999-10-202000-01-28Canada
B-plus - TabTabletOralChampion's Choice Advanced Nutrition Inc.1997-06-111999-08-28Canada
B50 ComplexCapsuleOralPreferred Nutrition Inc.2003-10-292005-08-04Canada
Balanced B 125 SrtTablet, extended releaseOralAnabolic Laboratories Inc.1981-12-311996-10-02Canada
BetacolCapsuleOralTherapeutic Foods Co.1989-12-151996-09-09Canada
Bev 29 TabTabletOralBeverly International Nutrition1987-12-311998-08-01Canada
Bev B-150TabletOralBeverly International Nutrition1986-12-311998-08-01Canada
Bev-lipo-1000TabletOralBeverly International Nutrition1986-12-311998-08-01Canada
BiosculptSolutionOralMaxion Nutrition Corp.2002-06-102004-07-20Canada
Choline & Inositol CapsCapsuleOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Choline and Inositol 250mg/250mgTabletOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Complete Mega BTabletOralGahler Enterprises Ltd.1985-12-312001-07-26Canada
Complete Multivitamins and Minerals Tablets Timed ReleaseTablet, extended releaseOralPharmetics (2011) Inc.1999-07-262009-07-30Canada
Complexe B Compose 75TabletOralLes Laboratoires Bio SantÉ Inc.1983-12-311996-09-10Canada
Daily Energy Brand B-complexCapsuleOralEnzymatic Therapy, Inc.2004-01-012008-07-25Canada
Dayclear Cough Cold and FluLiquidOralGm Pharmaceuticals2015-10-20Not applicableUs
Dayclear Sinus Pain and PressureLiquidOralGm Pharmaceuticals2015-08-10Not applicableUs
Derma-forceCapsuleOralPrairie Naturals1997-04-012006-09-20Canada
Dp 2000CapsuleOralPep Products Inc.1997-06-042006-08-23Canada
Essential B TabletsTabletOralGeneral Nutrition Canada Inc.1997-04-182006-08-03Canada
Fem - PmtTabletOralMetagenics, Inc.1998-02-252002-10-07Canada
First Aid Shot Therapy Hangover ReliefSolutionOralFirst Aid Beverages, Inc.2015-02-01Not applicableUs
First Aid Shot Therapy Pain ReliefLiquidOralFirst Aid Beverages, Inc.2013-09-05Not applicableUs
Folic Acid PlusTabletOralVita Health Products Inc2000-04-012002-07-31Canada
Formula CmTabletOralNutrivention Nutritional ProductsNot applicableNot applicableCanada
Formula LfTabletOralNumark Laboratories, Inc.2003-12-152009-07-31Canada
Forty Plus Vitamin SupplementTabletOralGarden State Nutritionals1998-10-162000-06-07Canada
Fusion PM Formula TabTabletOralL & S Research Corporation1993-12-311996-09-09Canada
Gabavale-5KitPhysician Therapeutics Llc2011-05-072016-10-13Us
GabazolamineKitPhysician Therapeutics Llc2011-07-072016-10-13Us
Gabazolamine-0.5KitPhysician Therapeutics Llc2011-07-072016-10-13Us
Gabazolpidem-5KitPhysician Therapeutics Llc2011-07-072016-10-13Us
GabitidineKitPhysician Therapeutics Llc2011-07-072016-10-13Us
GaboxetineKitPhysician Therapeutics Llc2011-07-072016-10-13Us
Gesticare DHAKitJazz Pharmaceuticals Commercial Corp.2008-10-01Not applicableUs
Gnc Choline/inositol 250mg TabletsTabletOralGeneral Nutrition Canada Inc.1997-04-182005-08-05Canada
Harvest Of Values All B Complex TabTabletOralHillestad Pharmaceuticals Usa1997-09-242009-09-22Canada
Hi Potency B Complex W Chelated MineralsTabletOralKlaire Labs Inc.1984-12-312004-01-19Canada
Hi Potency B52 B Complex TabTabletOralCountry Health Laboratories Ltd.1982-12-312001-07-27Canada
Hi Potency Stress B Tension With CTabletOralLee Adams Laboratories1982-12-312010-08-05Canada
Insur-all Vitamin SupplementTabletOralGarden State Nutritionals1998-10-162000-06-07Canada
Kroger Cough Cold and FluLiquidOralKroger2016-04-07Not applicableUs
Kroger Nitetime Cold and FluLiquidOralKroger2016-04-07Not applicableUs
Kroger Sinus Pain and PressureLiquidOralKroger2016-04-07Not applicableUs
Lipo-B-C TabTabletOralMetagenics, Inc.1989-12-311996-10-02Canada
Lipotropics 600 TabTabletOralGahler Enterprises Ltd.1981-12-312001-07-26Canada
Liqui B ComplexLiquidOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Liqui B Complex PlusLiquidOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Liqui VitaLiquidOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Liquid B Complex 50LiquidOralJamieson Laboratories Ltd1985-12-311997-08-13Canada
Low Potency B Complex TabTabletOralFlora Manufacturing And Distributing Ltd.1983-12-311999-10-18Canada
MangadynTabletOralNutri Dyn Products Ltd.1982-12-311997-08-22Canada
Mega 13 Multivitamin FormulaCapsuleOralVita Health Products Inc1988-12-311998-07-22Canada
Mini-B TabTabletOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Multi BTabletOralSeroyal International Inc.1988-12-312009-07-06Canada
Multi Vitamin-mineral FormulaTabletOralVita Health Products Inc1997-04-031998-01-16Canada
Nata KompleteTabletOralWh Nutritionals, Llc2011-06-252016-12-06Us
OnccorTabletOralSimone Protective Pharmaceuticals, Inc.Not applicableNot applicableCanada
One A Day TabTabletOralCountry Health Laboratories Ltd.1982-12-312001-07-27Canada
Orti BCapsuleOralSeroyal International Inc.1983-12-312008-10-09Canada
Palm Spring's PM Form TabTabletOralL & S Research Corporation1993-12-311996-09-09Canada
PhytopureCapsuleOralLaboratoire Lalco Inc.1993-12-312001-10-15Canada
Pour Ma SantéTabletOralProdemdis Enr.Not applicableNot applicableCanada
Red American Eagle Vitamin Supplement DrinkLiquidOralP.S.W.C. Co., Inc.Not applicableNot applicableCanada
SenophyllineKitPhysician Therapeutics Llc2011-07-072016-10-13Us
SentradineKitPhysician Therapeutics Llc2011-07-072016-10-13Us
Sentraflox Am-10KitPhysician Therapeutics Llc2011-07-072016-10-13Us
Sentralopram Am-10KitPhysician Therapeutics Llc2011-07-072016-10-13Us
Sentravil PM-25KitPhysician Therapeutics Llc2011-07-072016-10-13Us
Sentrazolam AmKitPhysician Therapeutics Llc2011-07-072016-10-13Us
Sentrazolpidem PM-5KitOralPhysician Therapeutics Llc2011-07-072016-10-13Us
SentroxatineKitPhysician Therapeutics Llc2011-02-172016-10-13Us
Spectrum 2 CapCapsuleOralNf Formulas Inc.1988-12-312008-06-26Canada
Stom #2CapsuleOralMorinda Canada1999-12-202001-07-23Canada
StrazepamKitPhysician Therapeutics Llc2011-02-152016-10-13Us
Stress B & C CapletTabletOralHealth Wise Nutrition Inc.1995-12-311998-08-25Canada
Stress B Capsules With Vitamin CCapsuleOralRheingold Food International Ltd.1987-12-312007-07-26Canada
Stress B With 1000 Mg Vitamin CTabletOralHolista Health (Canada) Inc.2002-11-132008-07-17Canada
Stress B&c TabTabletOralBioforce Canada Inc.1985-12-311997-04-04Canada
Stress Ctr SrtTablet, extended releaseOralBioenergy Inc.1979-12-311998-06-03Canada
Stress Formula B-comp + 500mg Vit C TabTabletOralQuest Vitamins A Div Of Purity Life Health Products1987-12-312002-07-29Canada
Stress Formula Multi-B Comp + 500mg Vit C CapCapsuleOralQuest Vitamins A Div Of Purity Life Health Products1987-12-312001-07-06Canada
Stress Formula Vit B With C ComplexTabletOralWatkins Incorporated1985-12-312000-01-15Canada
Stress Forte Plus Lipotropic FactorsTabletOralDouglas Laboratories1995-12-312009-09-29Canada
Stress Vitamin B With C Complex TabletsTabletOralPurity Life Health Products A Division Of Sunopta Inc.2002-06-012007-07-26Canada
StressmatesTabletOralTwin Laboratories Inc.1995-12-311999-11-10Canada
Super B Compound W 500mg Vit CTabletOralGahler Enterprises Ltd.1986-12-312000-08-01Canada
Super Daily No 2TabletOralW.R. Enterprises Inc.1990-12-312003-07-30Canada
Super Stress CapsulesCapsuleOralRheingold Food International Ltd.1987-12-311997-08-22Canada
Super Stress Mega B Plus 1000mg Vit C TabTabletOralQuest Vitamins A Div Of Purity Life Health Products1987-12-312001-07-06Canada
Super-pote Vitamin SupplementTabletOralGarden State Nutritionals1998-09-252000-06-07Canada
Teejel GelGelDental; TopicalPurdue Pharma1965-12-312002-07-30Canada
Texaclear Congestion and Pain Sinus ReliefLiquidOralGm Pharmaceuticals2014-10-21Not applicableUs
Texaclear Daytime Cough Cold/fluLiquidOralGm Pharmaceuticals2014-10-21Not applicableUs
Texaclear Night Time Cough Cold/fluLiquidOralGm Pharmaceuticals2014-10-23Not applicableUs
Time Release B 100 Compound - TabletTabletOralHealth Wise Nutrition Inc.1996-10-222002-07-18Canada
Timed Release B Complex 100 SrtTablet, extended releaseOralJamieson Laboratories Ltd1994-12-311997-08-13Canada
Timed Release B-complex 100Tablet, extended releaseOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Timed Release B-complex 50Tablet, extended releaseOralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
TrazamineKitPhysician Therapeutics Llc2011-02-032016-10-13Us
Trilisate TabTabletOralPurdue Pharma1979-12-312002-07-30Canada
Ultra HrTabletOralNatural Organics Inc.Not applicableNot applicableCanada
Usana Megavitamin Tablets - TabTabletOralUsana Health Sciences, Inc.1996-12-302000-09-11Canada
VanapainLiquidOralGm Pharmaceuticals2013-07-22Not applicableUs
Vanapain PMLiquidOralGm Pharmaceuticals2013-10-28Not applicableUs
Vit B Complex CtrTablet, extended releaseOralBioenergy Inc.1979-12-311998-06-03Canada
Vit-HA Multi Vitamin and Zinc SupplementTabletOralRheingold Food International Ltd.1994-12-312007-07-26Canada
Vita B Complex TabTabletOralNutrimetics International (Canada) Inc.1985-12-312000-07-19Canada
Vita-BTabletOralNutri Dyn Products Ltd.1984-12-311997-08-22Canada
Vita-worth B-complex TabletsTabletOralGeneral Nutrition Canada Inc.1997-04-182005-08-05Canada
Vitalife - CapsuleCapsuleOralHolista Health (Canada) Inc.1996-11-132002-08-06Canada
Vitamin B + C CapCapsuleOralFinlandia Consultants1990-12-311997-12-02Canada
Vitamin B Complex 100 TabTabletOralBioforce Canada Inc.1994-12-311997-04-04Canada
Vitamin B Complex 50TabletOralGfr Pharma Ltd.2002-10-102004-06-15Canada
Vitamin B Complex SupplTabletOralAvacare, Division Of Jeunique International Inc.1985-12-312006-07-20Canada
Vitamin B Complex W C TabTabletOralAlbi Imports Ltd.1979-12-312004-09-24Canada
Vitamin B Compound W C Tab 500mgTabletOralAdams Laboratories1979-12-312009-10-21Canada
Vitamin B Compound W Vit C 250mg TabTabletOralSwiss Herbal Remedies Ltd.1972-12-312003-09-10Canada
Vitamin B TabletsTabletOralWeider Health Products1985-12-311999-09-09Canada
Women's FormulaTabletOralPro Ma Systems1998-10-312007-09-25Canada
Categories
UNIIN91BDP6H0X
CAS number62-49-7
WeightAverage: 104.1708
Monoisotopic: 104.107539075
Chemical FormulaC5H14NO
InChI KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
InChI
InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
IUPAC Name
(2-hydroxyethyl)trimethylazanium
SMILES
C[N+](C)(C)CCO
Pharmacology
Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

Structured Indications Not Available
Pharmacodynamics

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Choline-phosphate cytidylyltransferase BProteinunknown
product of
HumanQ9Y5K3 details
AcetylcholinesteraseProteinunknown
product of
HumanP22303 details
Choline-phosphate cytidylyltransferase AProteinunknown
product of
HumanP49585 details
Phospholipase D2Proteinunknown
product of
HumanO14939 details
CholinesteraseProteinunknown
product of
HumanP06276 details
Phospholipase D1Proteinunknown
product of
HumanQ13393 details
Phosphoethanolamine/phosphocholine phosphataseProteinunknown
product of
HumanQ8TCT1 details
Neuronal acetylcholine receptor subunit alpha-7ProteinunknownNot AvailableHumanP36544 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

Oral rat LD50: 3400 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)DiseaseSMP00340
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDiseaseSMP00570
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDiseaseSMP00214
Glycine N-methyltransferase DeficiencyDiseaseSMP00222
sarcosine oncometabolite pathway DiseaseSMP02313
Phospholipid BiosynthesisMetabolicSMP00025
Betaine MetabolismMetabolicSMP00123
Cystathionine Beta-Synthase DeficiencyDiseaseSMP00177
Methionine MetabolismMetabolicSMP00033
Methionine Adenosyltransferase DeficiencyDiseaseSMP00221
HypermethioninemiaDiseaseSMP00341
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
BupropionThe serum concentration of Choline can be increased when it is combined with Bupropion.Approved
Food InteractionsNot Available
References
Synthesis Reference

Satishchandra P. Patel, Vinayak T. Bhalani, "Solid choline magnesium salicylate composition and method of preparing same." U.S. Patent US5043168, issued May, 1954.

US5043168
General ReferencesNot Available
External Links
ATC CodesN02BA03 — Choline salicylate
AHFS Codes
  • 56:24.00
  • 88:08.00
  • 88:30.00*
PDB Entries
FDA labelNot Available
MSDSDownload (73.6 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0Enrolling by InvitationBasic ScienceDietary Modifications / Nutrition1
1Not Yet RecruitingTreatmentChild's Development / Prenatal Stress1
1SuspendedTreatmentChild's Development / Pregnancy1
1, 2CompletedTreatmentAlcohol Related Neurodevelopmental Disorder / Fetal Alcohol Spectrum Disorders / Fetal Alcohol Syndrome (FAS) / Partial Fetal Alcohol Syndrome / Prenatal Alcohol Exposure1
2RecruitingTreatmentFetal Alcohol Spectrum Disorders1
4CompletedPreventionArsenic Metabolites Measured in Urine1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain1
4RecruitingTreatmentAutism, Early Infantile1
4TerminatedTreatmentInflammatory Reaction / Postoperative pain1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
ElixirOral
CapsuleOral
Tablet, extended releaseOral
TabletOral250 mg
TabletOral100 mg
TabletOral500 mg
CapsuleOral350 mg
Tablet, extended releaseOral400 mg
TabletOral200 mg
SolutionOral
LiquidOral
TabletOral
Kit
KitOral
GelDental; Topical
Prices
Unit descriptionCostUnit
Trilipix dr 135 mg capsule4.38USD capsule
Trilipix dr 45 mg capsule1.46USD capsule
Choline-10 tablet0.06USD tablet
Choline bitartrate crystals0.03USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point (°C)244-247 °C (as chloride salt)Not Available
boiling point (°C)113 °CNot Available
water solubilitySolubleNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.61 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.19 m3·mol-1ChemAxon
Polarizability12.57 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.964
Blood Brain Barrier+0.9214
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5169
P-glycoprotein inhibitor INon-inhibitor0.9881
P-glycoprotein inhibitor IINon-inhibitor0.9543
Renal organic cation transporterNon-inhibitor0.7651
CYP450 2C9 substrateNon-substrate0.7719
CYP450 2D6 substrateNon-substrate0.5882
CYP450 3A4 substrateNon-substrate0.5505
CYP450 1A2 substrateNon-inhibitor0.9193
CYP450 2C9 inhibitorNon-inhibitor0.9496
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9497
CYP450 3A4 inhibitorNon-inhibitor0.9904
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9936
Ames testNon AMES toxic0.9387
CarcinogenicityCarcinogens 0.5996
BiodegradationReady biodegradable0.7211
Rat acute toxicity2.0491 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8202
hERG inhibition (predictor II)Non-inhibitor0.8071
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-ea6f9c1150759c5be6c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-1900000000-cadf16d18f093e9b19d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bt9-9100000000-a2c328b7da5435b8e467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-6a7b57dbdf4560721722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-5900000000-87fdeef5275a74e78348View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0w29-5900000000-9b79cc5ff3b1ce17deb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-9200000000-fe62d5a4fbf492493d60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-3900000000-0b37e63e9c6b14a2e397View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-1900000000-391c1b7859a03e776123View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound 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 ParentsTetraalkylammonium salts / 1,2-aminoalcohols / Primary alcohols / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Organic cations
SubstituentsCholine / Tetraalkylammonium salt / 1,2-aminoalcohol / Alkanolamine / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organic salt / Primary alcohol / Organooxygen compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptorscholines (CHEBI:15354 ) / Pesticides (C00114 ) / a small molecule (CHOLINE )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Choline-phosphate cytidylyltransferase activity
Specific Function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1B
Uniprot ID:
Q9Y5K3
Uniprot Name:
Choline-phosphate cytidylyltransferase B
Molecular Weight:
41939.76 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Wang L, Magdaleno S, Tabas I, Jackowski S: Early embryonic lethality in mice with targeted deletion of the CTP:phosphocholine cytidylyltransferase alpha gene (Pcyt1a). Mol Cell Biol. 2005 Apr;25(8):3357-63. [PubMed:15798219 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Uniprot Name:
Acetylcholinesterase
Molecular Weight:
67795.525 Da
References
  1. Amenta F, Tayebati SK, Vitali D, Di Tullio MA: Association with the cholinergic precursor choline alphoscerate and the cholinesterase inhibitor rivastigmine: an approach for enhancing cholinergic neurotransmission. Mech Ageing Dev. 2006 Feb;127(2):173-9. Epub 2005 Nov 16. [PubMed:16297435 ]
  2. Longobardi F, Solfrizzo M, Compagnone D, Del Carlo M, Visconti A: Use of electrochemical biosensor and gas chromatography for determination of dichlorvos in wheat. J Agric Food Chem. 2005 Nov 30;53(24):9389-94. [PubMed:16302752 ]
  3. Durcan N, Costello RW, McLean WG, Blusztajn J, Madziar B, Fenech AG, Hall IP, Gleich GJ, McGarvey L, Walsh MT: Eosinophil-mediated cholinergic nerve remodeling. Am J Respir Cell Mol Biol. 2006 Jun;34(6):775-86. Epub 2006 Feb 2. [PubMed:16456188 ]
  4. Alkondon M, Albuquerque EX: Subtype-specific inhibition of nicotinic acetylcholine receptors by choline: a regulatory pathway. J Pharmacol Exp Ther. 2006 Jul;318(1):268-75. Epub 2006 Mar 24. [PubMed:16565162 ]
  5. Anzai J: [Use of biosensors for detecting organophosphorus agents]. Yakugaku Zasshi. 2006 Dec;126(12):1301-8. [PubMed:17139155 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Lipid binding
Specific Function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
Uniprot Name:
Choline-phosphate cytidylyltransferase A
Molecular Weight:
41730.67 Da
References
  1. Enaw JO, Zhu H, Yang W, Lu W, Shaw GM, Lammer EJ, Finnell RH: CHKA and PCYT1A gene polymorphisms, choline intake and spina bifida risk in a California population. BMC Med. 2006 Dec 21;4:36. [PubMed:17184542 ]
  2. Li L, She H, Yue SJ, Qin XQ, Guan CX, Liu HJ, Luo ZQ: Role of c-fos gene in vasoactive intestinal peptide promoted synthesis of pulmonary surfactant phospholipids. Regul Pept. 2007 May 3;140(3):117-24. Epub 2007 Jan 10. [PubMed:17218027 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Phospholipase d activity
Specific Function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis.
Gene Name:
PLD2
Uniprot ID:
O14939
Uniprot Name:
Phospholipase D2
Molecular Weight:
105986.1 Da
References
  1. Lee JS, Kim JH, Jang IH, Kim HS, Han JM, Kazlauskas A, Yagisawa H, Suh PG, Ryu SH: Phosphatidylinositol (3,4,5)-trisphosphate specifically interacts with the phox homology domain of phospholipase D1 and stimulates its activity. J Cell Sci. 2005 Oct 1;118(Pt 19):4405-13. [PubMed:16179605 ]
  2. Singh AT, Frohman MA, Stern PH: Parathyroid hormone stimulates phosphatidylethanolamine hydrolysis by phospholipase D in osteoblastic cells. Lipids. 2005 Nov;40(11):1135-40. [PubMed:16459925 ]
  3. Paruch S, Heinis M, Lemay J, Hoeffel G, Maranon C, Hosmalin A, Perianin A: CCR5 signaling through phospholipase D involves p44/42 MAP-kinases and promotes HIV-1 LTR-directed gene expression. FASEB J. 2007 Dec;21(14):4038-46. Epub 2007 Jul 12. [PubMed:17627030 ]
  4. Szumilo M, Rahden-Staron I: [Phospholipase D in mammalian cells: structure, properties, physiological and pathological role]. Postepy Hig Med Dosw (Online). 2006;60:421-30. [PubMed:16921342 ]
  5. Fensome-Green A, Cockcroft S: Reconstitution system based on cytosol-depleted cells to study the regulation of phospholipase D. Methods Mol Biol. 2006;332:299-310. [PubMed:16878701 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Uniprot Name:
Cholinesterase
Molecular Weight:
68417.575 Da
References
  1. Hsieh BC, Matsumoto K, Cheng TJ, Yuu G, Chen RL: Choline biosensor constructed with chitinous membrane from soldier crab and its application in measuring cholinesterase inhibitory activities. J Pharm Biomed Anal. 2007 Nov 30;45(4):673-8. Epub 2007 Jan 24. [PubMed:17329059 ]
  2. Amenta F, Tayebati SK, Vitali D, Di Tullio MA: Association with the cholinergic precursor choline alphoscerate and the cholinesterase inhibitor rivastigmine: an approach for enhancing cholinergic neurotransmission. Mech Ageing Dev. 2006 Feb;127(2):173-9. Epub 2005 Nov 16. [PubMed:16297435 ]
  3. Lurie S, Sadan O, Oron G, Fux A, Boaz M, Ezri T, Golan A, Bar J: Reduced pseudocholinesterase activity in patients with HELLP syndrome. Reprod Sci. 2007 Feb;14(2):192-6. [PubMed:17636231 ]
  4. Calaf GM, Roy D: Gene expression signature of parathion-transformed human breast epithelial cells. Int J Mol Med. 2007 May;19(5):741-50. [PubMed:17390078 ]
  5. Stoytcheva M, Zlatev R, Valdez B, Magnin JP, Velkova Z: Electrochemical sensor based on Arthrobacter globiformis for cholinesterase activity determination. Biosens Bioelectron. 2006 Jul 15;22(1):1-9. Epub 2005 Dec 20. [PubMed:16376069 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Phospholipase d activity
Specific Function:
Implicated as a critical step in numerous cellular pathways, including signal transduction, membrane trafficking, and the regulation of mitosis. May be involved in the regulation of perinuclear intravesicular membrane traffic (By similarity).
Gene Name:
PLD1
Uniprot ID:
Q13393
Uniprot Name:
Phospholipase D1
Molecular Weight:
124183.135 Da
References
  1. Lee JS, Kim JH, Jang IH, Kim HS, Han JM, Kazlauskas A, Yagisawa H, Suh PG, Ryu SH: Phosphatidylinositol (3,4,5)-trisphosphate specifically interacts with the phox homology domain of phospholipase D1 and stimulates its activity. J Cell Sci. 2005 Oct 1;118(Pt 19):4405-13. [PubMed:16179605 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Pyrophosphatase activity
Specific Function:
Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Uniprot Name:
Phosphoethanolamine/phosphocholine phosphatase
Molecular Weight:
29712.54 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
Uniprot Name:
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight:
56448.925 Da
References
  1. Zhao L, Kuo YP, George AA, Peng JH, Purandare MS, Schroeder KM, Lukas RJ, Wu J: Functional properties of homomeric, human alpha 7-nicotinic acetylcholine receptors heterologously expressed in the SH-EP1 human epithelial cell line. J Pharmacol Exp Ther. 2003 Jun;305(3):1132-41. Epub 2003 Mar 6. [PubMed:12626641 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Metal ion binding
Specific Function:
Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.
Gene Name:
CEPT1
Uniprot ID:
Q9Y6K0
Uniprot Name:
Choline/ethanolaminephosphotransferase 1
Molecular Weight:
46553.135 Da
References
  1. Wright MM, McMaster CR: PC and PE synthesis: mixed micellar analysis of the cholinephosphotransferase and ethanolaminephosphotransferase activities of human choline/ethanolamine phosphotransferase 1 (CEPT1). Lipids. 2002 Jul;37(7):663-72. [PubMed:12216837 ]
  2. Henneberry AL, Wistow G, McMaster CR: Cloning, genomic organization, and characterization of a human cholinephosphotransferase. J Biol Chem. 2000 Sep 22;275(38):29808-15. [PubMed:10893425 ]
  3. Henneberry AL, McMaster CR: Cloning and expression of a human choline/ethanolaminephosphotransferase: synthesis of phosphatidylcholine and phosphatidylethanolamine. Biochem J. 1999 Apr 15;339 ( Pt 2):291-8. [PubMed:10191259 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Ethanolamine kinase activity
Specific Function:
Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Uniprot Name:
Choline/ethanolamine kinase
Molecular Weight:
45270.99 Da
References
  1. Sher RB, Aoyama C, Huebsch KA, Ji S, Kerner J, Yang Y, Frankel WN, Hoppel CL, Wood PA, Vance DE, Cox GA: A rostrocaudal muscular dystrophy caused by a defect in choline kinase beta, the first enzyme in phosphatidylcholine biosynthesis. J Biol Chem. 2006 Feb 24;281(8):4938-48. Epub 2005 Dec 21. [PubMed:16371353 ]
  2. Eliyahu G, Kreizman T, Degani H: Phosphocholine as a biomarker of breast cancer: molecular and biochemical studies. Int J Cancer. 2007 Apr 15;120(8):1721-30. [PubMed:17236204 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Choline o-acetyltransferase activity
Specific Function:
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name:
CHAT
Uniprot ID:
P28329
Uniprot Name:
Choline O-acetyltransferase
Molecular Weight:
82535.025 Da
References
  1. Kim AR, Dobransky T, Rylett RJ, Shilton BH: Surface-entropy reduction used in the crystallization of human choline acetyltransferase. Acta Crystallogr D Biol Crystallogr. 2005 Sep;61(Pt 9):1306-10. Epub 2005 Aug 16. [PubMed:16131766 ]
  2. Bikopoulos GJ, Hoque T, Webb RA: Infection with the cestode Hymenolepis diminuta induces changes in acetylcholine metabolism and muscarinic receptor mRNA expression in the rat jejunum. Parasitol Res. 2006 Aug;99(3):231-7. Epub 2006 Mar 16. [PubMed:16541262 ]
  3. Opazo P, Saud K, de Saint Pierre M, Cardenas AM, Allen DD, Segura-Aguilar J, Caviedes R, Caviedes P: Knockdown of amyloid precursor protein normalizes cholinergic function in a cell line derived from the cerebral cortex of a trisomy 16 mouse: An animal model of down syndrome. J Neurosci Res. 2006 Nov 1;84(6):1303-10. [PubMed:16941497 ]
  4. Kim AR, Rylett RJ, Shilton BH: Substrate binding and catalytic mechanism of human choline acetyltransferase. Biochemistry. 2006 Dec 12;45(49):14621-31. [PubMed:17144655 ]
  5. Mehl A, Schanke TM, Torvik A, Fonnum F: The effect of trichlorfon and methylazoxymethanol on the development of guinea pig cerebellum. Toxicol Appl Pharmacol. 2007 Mar;219(2-3):128-35. Epub 2006 Nov 1. [PubMed:17150236 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Signal transducer activity
Specific Function:
Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:
CHKA
Uniprot ID:
P35790
Uniprot Name:
Choline kinase alpha
Molecular Weight:
52248.53 Da
References
  1. Li Z, Agellon LB, Vance DE: Phosphatidylcholine homeostasis and liver failure. J Biol Chem. 2005 Nov 11;280(45):37798-802. Epub 2005 Sep 6. [PubMed:16144842 ]
  2. Glunde K, Raman V, Mori N, Bhujwalla ZM: RNA interference-mediated choline kinase suppression in breast cancer cells induces differentiation and reduces proliferation. Cancer Res. 2005 Dec 1;65(23):11034-43. [PubMed:16322253 ]
  3. Malito E, Sekulic N, Too WC, Konrad M, Lavie A: Elucidation of human choline kinase crystal structures in complex with the products ADP or phosphocholine. J Mol Biol. 2006 Nov 24;364(2):136-51. Epub 2006 Sep 3. [PubMed:17007874 ]
  4. Eliyahu G, Kreizman T, Degani H: Phosphocholine as a biomarker of breast cancer: molecular and biochemical studies. Int J Cancer. 2007 Apr 15;120(8):1721-30. [PubMed:17236204 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Flavin adenine dinucleotide binding
Specific Function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Uniprot Name:
Choline dehydrogenase, mitochondrial
Molecular Weight:
65358.005 Da
References
  1. Slow S, Garrow TA: Liver choline dehydrogenase and kidney betaine-homocysteine methyltransferase expression are not affected by methionine or choline intake in growing rats. J Nutr. 2006 Sep;136(9):2279-83. [PubMed:16920841 ]
  2. Bidulescu A, Chambless LE, Siega-Riz AM, Zeisel SH, Heiss G: Usual choline and betaine dietary intake and incident coronary heart disease: the Atherosclerosis Risk in Communities (ARIC) study. BMC Cardiovasc Disord. 2007 Jul 13;7:20. [PubMed:17629908 ]
  3. Quan R, Shang M, Zhang H, Zhao Y, Zhang J: Engineering of enhanced glycine betaine synthesis improves drought tolerance in maize. Plant Biotechnol J. 2004 Nov;2(6):477-86. [PubMed:17147620 ]
  4. Dalmeijer GW, Olthof MR, Verhoef P, Bots ML, van der Schouw YT: Prospective study on dietary intakes of folate, betaine, and choline and cardiovascular disease risk in women. Eur J Clin Nutr. 2008 Mar;62(3):386-94. Epub 2007 Mar 21. [PubMed:17375117 ]
  5. da Costa KA, Kozyreva OG, Song J, Galanko JA, Fischer LM, Zeisel SH: Common genetic polymorphisms affect the human requirement for the nutrient choline. FASEB J. 2006 Jul;20(9):1336-44. [PubMed:16816108 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Uniprot Name:
Solute carrier family 22 member 2
Molecular Weight:
62579.99 Da
References
  1. Sweet DH, Miller DS, Pritchard JB: Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9. Epub 2001 Sep 11. [PubMed:11553644 ]
  2. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  3. Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
  4. Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798 ]
  5. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  6. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
  7. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
  8. Budiman T, Bamberg E, Koepsell H, Nagel G: Mechanism of electrogenic cation transport by the cloned organic cation transporter 2 from rat. J Biol Chem. 2000 Sep 22;275(38):29413-20. [PubMed:10889205 ]
  9. Pan G, Winter TN, Roberts JC, Fairbanks CA, Elmquist WF: Organic cation uptake is enhanced in bcrp1-transfected MDCKII cells. Mol Pharm. 2010 Feb 1;7(1):138-45. doi: 10.1021/mp900177r. [PubMed:19886673 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Uniprot Name:
Solute carrier family 22 member 1
Molecular Weight:
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
  2. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
  3. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
  4. Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
  5. Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [PubMed:9195965 ]
  6. Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798 ]
  7. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  8. Jonker JW, Wagenaar E, Mol CA, Buitelaar M, Koepsell H, Smit JW, Schinkel AH: Reduced hepatic uptake and intestinal excretion of organic cations in mice with a targeted disruption of the organic cation transporter 1 (Oct1 [Slc22a1]) gene. Mol Cell Biol. 2001 Aug;21(16):5471-7. [PubMed:11463829 ]
  9. Sinclair CJ, Chi KD, Subramanian V, Ward KL, Green RM: Functional expression of a high affinity mammalian hepatic choline/organic cation transporter. J Lipid Res. 2000 Nov;41(11):1841-8. [PubMed:11060354 ]
  10. Green RM, Lo K, Sterritt C, Beier DR: Cloning and functional expression of a mouse liver organic cation transporter. Hepatology. 1999 May;29(5):1556-62. [PubMed:10216142 ]
  11. Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [PubMed:8955087 ]
  12. Sweet DH, Miller DS, Pritchard JB: Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9. Epub 2001 Sep 11. [PubMed:11553644 ]
  13. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]
  14. Gorboulev V, Volk C, Arndt P, Akhoundova A, Koepsell H: Selectivity of the polyspecific cation transporter rOCT1 is changed by mutation of aspartate 475 to glutamate. Mol Pharmacol. 1999 Dec;56(6):1254-61. [PubMed:10570053 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Uniprot Name:
Solute carrier family 22 member 3
Molecular Weight:
61279.485 Da
References
  1. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [PubMed:9632645 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Uniprot Name:
Solute carrier family 22 member 5
Molecular Weight:
62751.08 Da
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255 ]
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
  3. Tamai I, Ohashi R, Nezu JI, Sai Y, Kobayashi D, Oku A, Shimane M, Tsuji A: Molecular and functional characterization of organic cation/carnitine transporter family in mice. J Biol Chem. 2000 Dec 22;275(51):40064-72. [PubMed:11010964 ]
  4. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Uniprot Name:
Solute carrier family 22 member 4
Molecular Weight:
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Choline transmembrane transporter activity
Specific Function:
Choline transporter. May be involved in membrane synthesis and myelin production.
Gene Name:
SLC44A1
Uniprot ID:
Q8WWI5
Uniprot Name:
Choline transporter-like protein 1
Molecular Weight:
73301.28 Da
References
  1. Inazu M, Takeda H, Matsumiya T: Molecular and functional characterization of an Na+-independent choline transporter in rat astrocytes. J Neurochem. 2005 Sep;94(5):1427-37. Epub 2005 Jul 5. [PubMed:16000150 ]
  2. Fullerton MD, Wagner L, Yuan Z, Bakovic M: Impaired trafficking of choline transporter-like protein-1 at plasma membrane and inhibition of choline transport in THP-1 monocyte-derived macrophages. Am J Physiol Cell Physiol. 2006 Apr;290(4):C1230-8. Epub 2005 Nov 30. [PubMed:16319125 ]
  3. Tomi M, Arai K, Tachikawa M, Hosoya K: Na(+)-independent choline transport in rat retinal capillary endothelial cells. Neurochem Res. 2007 Nov;32(11):1833-42. Epub 2007 May 23. [PubMed:17520363 ]
  4. Ishiguro N, Oyabu M, Sato T, Maeda T, Minami H, Tamai I: Decreased biosynthesis of lung surfactant constituent phosphatidylcholine due to inhibition of choline transporter by gefitinib in lung alveolar cells. Pharm Res. 2008 Feb;25(2):417-27. Epub 2007 Jul 12. [PubMed:17624579 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
SLC44A4
Uniprot ID:
Q53GD3
Uniprot Name:
Choline transporter-like protein 4
Molecular Weight:
79252.975 Da
References
  1. Tomi M, Arai K, Tachikawa M, Hosoya K: Na(+)-independent choline transport in rat retinal capillary endothelial cells. Neurochem Res. 2007 Nov;32(11):1833-42. Epub 2007 May 23. [PubMed:17520363 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Signal transducer activity
Specific Function:
Isoform 1, but not isoform 3, exhibits some choline transporter activity.
Gene Name:
SLC44A2
Uniprot ID:
Q8IWA5
Uniprot Name:
Choline transporter-like protein 2
Molecular Weight:
80122.695 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
SLC44A3
Uniprot ID:
Q8N4M1
Uniprot Name:
Choline transporter-like protein 3
Molecular Weight:
73782.63 Da
References
  1. Tomi M, Arai K, Tachikawa M, Hosoya K: Na(+)-independent choline transport in rat retinal capillary endothelial cells. Neurochem Res. 2007 Nov;32(11):1833-42. Epub 2007 May 23. [PubMed:17520363 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Choline:sodium symporter activity
Specific Function:
Imports choline from the extracellular space to the neuron with high affinity. Choline uptake is the rate-limiting step in acetylcholine synthesis. Sodium ion- and chloride ion-dependent.
Gene Name:
SLC5A7
Uniprot ID:
Q9GZV3
Uniprot Name:
High affinity choline transporter 1
Molecular Weight:
63202.985 Da
References
  1. Ribeiro FM, Black SA, Cregan SP, Prado VF, Prado MA, Rylett RJ, Ferguson SS: Constitutive high-affinity choline transporter endocytosis is determined by a carboxyl-terminal tail dileucine motif. J Neurochem. 2005 Jul;94(1):86-96. [PubMed:15953352 ]
  2. Geldenhuys WJ, Lockman PR, Philip AE, McAfee JH, Miller BL, McCurdy CR, Allen DD: Inhibition of choline uptake by N-cyclohexylcholine, a high affinity ligand for the choline transporter at the blood-brain barrier. J Drug Target. 2005 May;13(4):259-66. [PubMed:16051538 ]
  3. Guidry G, Willison BD, Blakely RD, Landis SC, Habecker BA: Developmental expression of the high affinity choline transporter in cholinergic sympathetic neurons. Auton Neurosci. 2005 Dec 30;123(1-2):54-61. Epub 2005 Nov 8. [PubMed:16278103 ]
  4. Parikh V, Sarter M: Cortical choline transporter function measured in vivo using choline-sensitive microelectrodes: clearance of endogenous and exogenous choline and effects of removal of cholinergic terminals. J Neurochem. 2006 Apr;97(2):488-503. Epub 2006 Mar 15. [PubMed:16539662 ]
  5. Parikh V, Apparsundaram S, Kozak R, Richards JB, Sarter M: Reduced expression and capacity of the striatal high-affinity choline transporter in hyperdopaminergic mice. Neuroscience. 2006 Aug 11;141(1):379-89. Epub 2006 May 3. [PubMed:16675138 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:20