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Record Information
Version1.0
Creation Date2016-09-30 22:19:35 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0000097
Secondary Accession Numbers
  • BMDB00097
Metabolite Identification
Common NameCholine
DescriptionCholine, also known as bilineurine or choline ion, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Choline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Choline exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Choline exists in all living species, ranging from bacteria to humans. Choline participates in a number of enzymatic reactions, within cattle. In particular, Choline can be biosynthesized from acetylcholine; which is mediated by the enzyme acetylcholinesterase. In addition, Choline can be converted into acetylcholine; which is catalyzed by the enzyme choline O-acetyltransferase. In cattle, choline is involved in the metabolic pathway called phospholipid biosynthesis pathway.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC5H14NO
Average Molecular Weight104.1708
Monoisotopic Molecular Weight104.107539075
IUPAC Name(2-hydroxyethyl)trimethylazanium
Traditional Namecholine
CAS Registry Number62-49-7
SMILES
C[N+](C)(C)CCO
InChI Identifier
InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChI KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
Chemical Taxonomy
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
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Mitochondria
  • Myelin sheath
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point302 - 303 °C (chloride salt)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-9100000000-69389426dd865af031f9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9300000000-ca1b0086d4882b00b395View in MoNA
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-QQ , positivesplash10-0w29-5900000000-9b79cc5ff3b1ce17deb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9200000000-fe62d5a4fbf492493d60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-3900000000-0b37e63e9c6b14a2e397View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-6a7b57dbdf4560721722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-5900000000-87fdeef5275a74e78348View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-1900000000-391c1b7859a03e776123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-43b0f930ff04f7a48a59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9400000000-ab7cc75a8e0d3cc49449View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-0b94edfd44e38b20b8d3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Mitochondria
  • Myelin sheath
  • Nucleus
Biospecimen Locations
  • Basal Ganglia
  • Bladder
  • Blood
  • Brain
  • Colostrum
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Basal GangliaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified3.75-4.45 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified20+/-4 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified345+/-109 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified15+/-7 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
MilkDetected and Quantified150 - 997 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified152 - 479 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified106.5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified180 - 479 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified206 +/- 14 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified242 +/- 10 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified235 +/- 8 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified214 +/- 17 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified298.26 +/- 146.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified310.54 +/- 77.69 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified214.22 +/- 58.37 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified34-153 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified107.79 +/- 4.65 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified118.5 +/- 13.32 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified125.57 +/- 11.43 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified71-137 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified76.73 +/- 5.28 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified10-125 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified4-40 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified14.7 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified16.9 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified19.8 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified17.2 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified105+/-59 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Ruminal FluidDetected and Quantified17.54 +/- 6.66 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified13.1 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified16.7 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified24.6 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified17.5 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified13 +/- 3 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified17 +/- 6 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified25 +/- 13 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified18 +/- 7 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Semimembranosus MuscleDetected and Quantified15+/-6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
SpleenExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified177+/-71 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Heat stress
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
Ruminal FluidDetected and Quantified24.55 +/- 12.36 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000097
DrugBank IDDB00122
Phenol Explorer Compound IDNot Available
FooDB IDFDB000710
KNApSAcK IDC00007298
Chemspider ID299
KEGG Compound IDC00114
BioCyc IDCHOLINE
BiGG ID33910
Wikipedia LinkCholine
METLIN ID56
PubChem Compound305
PDB IDNot Available
ChEBI ID15354
References
Synthesis ReferenceHasegawa, Yoichi; Hyoda, Shunji; Sawada, Hirotoshi; Baba, Masakatsu. Preparation of high-purity organic carboxylic acid choline salts and choline. Jpn. Kokai Tokkyo Koho (1999), 9 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zeisel SH, Char D, Sheard NF: Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas. J Nutr. 1986 Jan;116(1):50-8. doi: 10.1093/jn/116.1.50. [PubMed:3944656 ]
  2. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  3. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  4. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  5. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  6. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  7. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  9. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Phosphatase that has high activity toward pyridoxal 5'-phosphate (PLP). Also active at much lower level toward pyrophosphate, phosphoethanolamine (PEA), phosphocholine (PCho), phospho-l-tyrosine, fructose-6-phosphate, p-nitrophenyl phosphate, and h-glycerophosphate (By similarity).
Gene Name:
PHOSPHO2
Uniprot ID:
Q2KI06
Molecular weight:
27751.0
Reactions
Phosphorylcholine → Cholinedetails
General function:
Involved in carnitine O-octanoyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:
CROT
Uniprot ID:
O19094
Molecular weight:
70263.0
Reactions
Choline → Acetylcholinedetails
General function:
Energy production and conversion
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Hydrolyzes lysoglycerophospholipids to produce lysophosphatidic acid (LPA) and the corresponding amines. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q3T0T0
Molecular weight:
37653.0
Reactions
Citicoline → Glycerol 3-phosphate + Cholinedetails
General function:
Lipid transport and metabolism
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft.
Gene Name:
ACHE
Uniprot ID:
P23795
Molecular weight:
67664.0
Reactions
Acetylcholine → Cholinedetails
General function:
Involved in NAPE-specific phospholipase D activity
Specific function:
5'->3' DNA exonuclease which digests single-stranded DNA (ssDNA) (By similarity). Regulates inflammatory cytokine responses via the degradation of nucleic acids, by reducing the concentration of ssDNA able to stimulate TLR9, a nucleotide-sensing receptor in collaboration with PLD4 (By similarity). May be important in myotube formation. Plays a role in lysosomal homeostasis. Involved in the regulation of endosomal protein sorting (By similarity).
Gene Name:
PLD3
Uniprot ID:
Q2KJJ8
Molecular weight:
54619.0
General function:
Lipid transport and metabolism
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters (By similarity).
Gene Name:
BCHE
Uniprot ID:
P32749
Molecular weight:
68867.0
General function:
Lipid transport and metabolism
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis.
Gene Name:
PLD2
Uniprot ID:
Q0V8L6
Molecular weight:
105766.0
General function:
Carbohydrate transport and metabolism
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, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase (By similarity).
Gene Name:
SLC22A1
Uniprot ID:
A7MBE0
Molecular weight:
62502.0
General function:
Involved in transport
Specific function:
Choline transporter.
Gene Name:
SLC44A2
Uniprot ID:
A5D7H3
Molecular weight:
80027.0
General function:
Not Available
Specific function:
Choline transporter that plays a role in the choline-acetylcholine system and is required to the efferent innervation of hair cells in the olivocochlear bundle for the maintenance of physiological function of outer hair cells and the protection of hair cells from acoustic injury (By similarity). Also described as a thiamine pyrophosphate transporter in colon, may mediate the absorption of microbiota-generated thiamine pyrophosphate and contribute to host thiamine (vitamin B1) homeostasis (By similarity).
Gene Name:
SLC44A4
Uniprot ID:
A3KMY4
Molecular weight:
78938.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
SLC44A3
Uniprot ID:
A5PK40
Molecular weight:
73220.0
General function:
Amino acid transport and metabolism
Specific function:
Functions as a sodium-dependent amino acid transporter. Mediates the saturable, pH-sensitive and electrogenic cotransport of neutral amino acids and sodium ions with a stoichiometry of 1:1. May function in the transport of amino acids at the blood-brain barrier and in the supply of maternal nutrients to the fetus through the placenta (By similarity).
Gene Name:
SLC38A2
Uniprot ID:
A2VE31
Molecular weight:
56214.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SLC5A7
Uniprot ID:
Q2KI26
Molecular weight:
63385.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
CHKA
Uniprot ID:
F1MI39
Molecular weight:
64756.0
Reactions
Choline + Adenosine triphosphate → Phosphorylcholine + ADPdetails
Choline → Phosphorylcholinedetails
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
Phosphatidylcholine + L-Serine → an L-1-Phosphatidylserine + Cholinedetails
PC(14:0/14:0) + L-Serine → Choline + PS(14:0/14:0)details
PC(14:0/14:1(9Z)) + L-Serine → Choline + PS(14:0/14:1(9Z))details
PC(14:0/16:0) + L-Serine → Choline + PS(14:0/16:0)details
PC(14:0/16:1(9Z)) + L-Serine → Choline + PS(14:0/16:1(9Z))details
PC(14:0/18:0) + L-Serine → Choline + PS(14:0/18:0)details
PC(14:0/18:1(9Z)) + L-Serine → Choline + PS(14:0/18:1(9Z))details
PC(14:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(14:0/18:2(9Z,12Z))details
PC(14:0/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(14:0/18:3(9Z,12Z,15Z))details
PC(14:0/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(14:0/20:3(8Z,11Z,14Z))details
PC(14:0/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(14:0/20:4(5Z,8Z,11Z,14Z))details
PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(14:1(9Z)/14:1(9Z)) + L-Serine → Choline + PS(14:1(9Z)/14:1(9Z))details
PC(14:1(9Z)/16:0) + L-Serine → Choline + PS(14:1(9Z)/16:0)details
PC(14:1(9Z)/16:1(9Z)) + L-Serine → Choline + PS(14:1(9Z)/16:1(9Z))details
PC(14:1(9Z)/18:0) + L-Serine → Choline + PS(14:1(9Z)/18:0)details
PC(14:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(14:1(9Z)/18:1(9Z))details
PC(14:1(9Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(14:1(9Z)/18:2(9Z,12Z))details
PC(14:1(9Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(14:1(9Z)/18:3(9Z,12Z,15Z))details
PC(14:1(9Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(14:1(9Z)/20:3(8Z,11Z,14Z))details
PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))details
PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(16:0/16:1(9Z)) + L-Serine → Choline + PS(16:0/16:1(9Z))details
PC(16:0/18:0) + L-Serine → Choline + PS(16:0/18:0)details
PC(16:0/18:1(11Z)) + L-Serine → Choline + PS(16:0/18:1(11Z))details
PC(16:0/18:1(9Z)) + L-Serine → Choline + PS(16:0/18:1(9Z))details
PC(16:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(16:0/18:2(9Z,12Z))details
PC(16:0/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(16:0/18:3(6Z,9Z,12Z))details
PC(16:0/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(16:0/18:3(9Z,12Z,15Z))details
PC(16:0/20:0) + L-Serine → Choline + PS(16:0/20:0)details
PC(16:0/20:1(11Z)) + L-Serine → Choline + PS(16:0/20:1(11Z))details
PC(16:0/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(16:0/20:3(8Z,11Z,14Z))details
PC(16:0/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(16:0/20:4(5Z,8Z,11Z,14Z))details
PC(16:0/22:0) + L-Serine → Choline + PS(16:0/22:0)details
PC(16:0/22:1(13Z)) + L-Serine → Choline + PS(16:0/22:1(13Z))details
PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(16:1(9Z)/16:1(9Z)) + L-Serine → Choline + PS(16:1(9Z)/16:1(9Z))details
PC(16:1(9Z)/18:0) + L-Serine → Choline + PS(16:1(9Z)/18:0)details
PC(16:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(16:1(9Z)/18:1(9Z))details
PC(16:1(9Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(16:1(9Z)/18:2(9Z,12Z))details
PC(16:1(9Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(16:1(9Z)/18:3(9Z,12Z,15Z))details
PC(16:1(9Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(16:1(9Z)/20:3(8Z,11Z,14Z))details
PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))details
PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(18:0/18:0) + L-Serine → Choline + PS(18:0/18:0)details
PC(18:0/18:1(11Z)) + L-Serine → Choline + PS(18:0/18:1(11Z))details
PC(18:0/18:1(9Z)) + L-Serine → Choline + PS(18:0/18:1(9Z))details
PC(18:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:0/18:2(9Z,12Z))details
PC(18:0/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(18:0/18:3(6Z,9Z,12Z))details
PC(18:0/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:0/18:3(9Z,12Z,15Z))details
PC(18:0/20:0) + L-Serine → Choline + PS(18:0/20:0)details
PC(18:0/20:1(11Z)) + L-Serine → Choline + PS(18:0/20:1(11Z))details
PC(18:0/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:0/20:3(8Z,11Z,14Z))details
PC(18:0/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(18:0/20:4(5Z,8Z,11Z,14Z))details
PC(18:0/20:4(8Z,11Z,14Z,17Z)) + L-Serine → Choline + PS(18:0/20:4(8Z,11Z,14Z,17Z))details
PC(18:0/22:0) + L-Serine → Choline + PS(18:0/22:0)details
PC(18:0/22:1(13Z)) + L-Serine → Choline + PS(18:0/22:1(13Z))details
PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z))details
PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(18:1(11Z)/18:1(11Z)) + L-Serine → Choline + PS(18:1(11Z)/18:1(11Z))details
PC(18:1(11Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:1(11Z)/18:2(9Z,12Z))details
PC(18:1(11Z)/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(18:1(11Z)/18:3(6Z,9Z,12Z))details
PC(18:1(11Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:1(11Z)/18:3(9Z,12Z,15Z))details
PC(18:1(11Z)/20:0) + L-Serine → Choline + PS(18:1(11Z)/20:0)details
PC(18:1(11Z)/20:1(11Z)) + L-Serine → Choline + PS(18:1(11Z)/20:1(11Z))details
PC(18:1(11Z)/22:0) + L-Serine → Choline + PS(18:1(11Z)/22:0)details
PC(18:1(11Z)/22:1(13Z)) + L-Serine → Choline + PS(18:1(11Z)/22:1(13Z))details
PC(18:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(18:1(9Z)/18:1(9Z))details
PC(18:1(9Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:1(9Z)/18:2(9Z,12Z))details
PC(18:1(9Z)/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(18:1(9Z)/18:3(6Z,9Z,12Z))details
PC(18:1(9Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:1(9Z)/18:3(9Z,12Z,15Z))details
PC(18:1(9Z)/20:0) + L-Serine → Choline + PS(18:1(9Z)/20:0)details
PC(18:1(9Z)/20:1(11Z)) + L-Serine → Choline + PS(18:1(9Z)/20:1(11Z))details
PC(18:1(9Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:1(9Z)/20:3(8Z,11Z,14Z))details
PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))details
PC(18:1(9Z)/22:0) + L-Serine → Choline + PS(18:1(9Z)/22:0)details
PC(18:1(9Z)/22:1(13Z)) + L-Serine → Choline + PS(18:1(9Z)/22:1(13Z))details
PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(18:2(9Z,12Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:2(9Z,12Z))details
PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))details
PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))details
PC(18:2(9Z,12Z)/20:0) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:0)details
PC(18:2(9Z,12Z)/20:1(11Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:1(11Z))details
PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))details
PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))details
PC(18:2(9Z,12Z)/22:0) + L-Serine → Choline + PS(18:2(9Z,12Z)/22:0)details
PC(18:2(9Z,12Z)/22:1(13Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/22:1(13Z))details
PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))details
PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))details
PC(18:3(6Z,9Z,12Z)/20:0) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/20:0)details
PC(18:3(6Z,9Z,12Z)/20:1(11Z)) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/20:1(11Z))details
PC(18:3(6Z,9Z,12Z)/22:0) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/22:0)details
PC(18:3(6Z,9Z,12Z)/22:1(13Z)) + L-Serine → Choline + PS(18:3(6Z,9Z,12Z)/22:1(13Z))details
PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))details
PC(18:3(9Z,12Z,15Z)/20:0) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/20:0)details
PC(18:3(9Z,12Z,15Z)/20:1(11Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/20:1(11Z))details
PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))details
PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))details
PC(18:3(9Z,12Z,15Z)/22:0) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/22:0)details
PC(18:3(9Z,12Z,15Z)/22:1(13Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/22:1(13Z))details
PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(20:0/20:0) + L-Serine → Choline + PS(20:0/20:0)details
PC(20:0/20:1(11Z)) + L-Serine → Choline + PS(20:0/20:1(11Z))details
PC(20:0/22:0) + L-Serine → Choline + PS(20:0/22:0)details
PC(20:0/22:1(13Z)) + L-Serine → Choline + PS(20:0/22:1(13Z))details
PC(20:1(11Z)/20:1(11Z)) + L-Serine → Choline + PS(20:1(11Z)/20:1(11Z))details
PC(20:1(11Z)/22:0) + L-Serine → Choline + PS(20:1(11Z)/22:0)details
PC(20:1(11Z)/22:1(13Z)) + L-Serine → Choline + PS(20:1(11Z)/22:1(13Z))details
PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))details
PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))details
PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))details
PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
PC(22:0/22:0) + L-Serine → Choline + PS(22:0/22:0)details
PC(22:0/22:1(13Z)) + L-Serine → Choline + PS(22:0/22:1(13Z))details
PC(22:1(13Z)/22:1(13Z)) + L-Serine → Choline + PS(22:1(13Z)/22:1(13Z))details
PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details
General function:
Not Available
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
E1BES2
Molecular weight:
65518.0
Reactions
Choline + Acceptor → Betaine aldehyde + Reduced acceptordetails
Choline + Acceptor → Betaine + Reduced acceptordetails