Record Information
Version1.0
Created at2020-03-18 23:21:22 UTC
Updated at2022-12-13 23:36:26 UTC
CannabisDB IDCDB006137
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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, such as Cannabis, 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.
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 Weight104.17
Monoisotopic Molecular Weight104.1075
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point302 - 303 °C (chloride salt)Not Available
Boiling Point113 °CWikipedia
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Choline O-acetyltransferaseCHAT10q11.2P28329 details
Phospholipase D2PLD217p13.1O14939 details
Phospholipase D1PLD13q26Q13393 details
Choline dehydrogenase, mitochondrialCHDH3p21.1Q8NE62 details
AcetylcholinesteraseACHE7q22P22303 details
CholinesteraseBCHE3q26.1-q26.2P06276 details
Choline-phosphate cytidylyltransferase BPCYT1BXp22.11Q9Y5K3 details
Choline-phosphate cytidylyltransferase APCYT1A3q29P49585 details
Choline/ethanolamine kinaseCHKB22q13.33Q9Y259 details
Choline kinase alphaCHKA11q13.2P35790 details
Alcohol dehydrogenase class-3ADH54q23P11766 details
Alcohol dehydrogenase 1BADH1B4q23P00325 details
Alcohol dehydrogenase class 4 mu/sigma chainADH74q23-q24P40394 details
Alcohol dehydrogenase 1AADH1A4q23P07327 details
Alcohol dehydrogenase 6ADH64q23P28332 details
Alcohol dehydrogenase 1CADH1C4q23P00326 details
Phosphoethanolamine/phosphocholine phosphatasePHOSPHO117q21.32Q8TCT1 details
Choline/ethanolaminephosphotransferase 1CEPT11p13.3Q9Y6K0 details
Phospholipase D3PLD319q13.2Q8IV08 details
Phospholipase D4PLD414q32.33Q96BZ4 details
Glycerophosphodiester phosphodiesterase 1GDE116p12-p11.2Q9NZC3 details
Phospholipase D1 variantQ59EA4 details
Phospholipase D6PLD617p11.2Q8N2A8 details
Glycerophosphocholine phosphodiesterase GPCPD1GPCPD120p12.3Q9NPB8 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Choline transporter-like protein 1SLC44A19q31.2Q8WWI5 details
High affinity choline transporter 1SLC5A72q12Q9GZV3 details
Solute carrier family 22 member 1SLC22A16q26O15245 details
Choline transporter-like protein 4SLC44A46p21.3Q53GD3 details
Choline transporter-like protein 2SLC44A219p13.1Q8IWA5 details
Choline transporter-like protein 3SLC44A31p21.3Q8N4M1 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Alcohol dehydrogenase class-3ADH54q23P11766 details
Alcohol dehydrogenase 1BADH1B4q23P00325 details
Alcohol dehydrogenase class 4 mu/sigma chainADH74q23-q24P40394 details
Alcohol dehydrogenase 1AADH1A4q23P07327 details
Alcohol dehydrogenase 6ADH64q23P28332 details
Alcohol dehydrogenase 1CADH1C4q23P00326 details
Phosphoethanolamine/phosphocholine phosphatasePHOSPHO117q21.32Q8TCT1 details
Choline/ethanolaminephosphotransferase 1CEPT11p13.3Q9Y6K0 details
Glycerophosphodiester phosphodiesterase 1GDE116p12-p11.2Q9NZC3 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase D2PLD217p13.1O14939 details
AcetylcholinesteraseACHE7q22P22303 details
Alcohol dehydrogenase class 4 mu/sigma chainADH74q23-q24P40394 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified1.418 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.853 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified1.128 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified1.00629 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.931 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified1.0750 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000097
DrugBank IDDB00122
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000710
KNApSAcK IDC00007298
Chemspider ID299
KEGG Compound IDC00114
BioCyc IDCHOLINE
BiGG ID33910
Wikipedia LinkCholine
METLIN ID56
PubChem Compound305
PDB IDNot Available
ChEBI ID15354
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 42 proteins in total.

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name:
CHAT
Uniprot ID:
P28329
Molecular weight:
70425.285
General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
General function:
Involved in protein binding
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
Molecular weight:
124183.135
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Molecular weight:
65358.005
General function:
Involved in carboxylesterase 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
Molecular weight:
67795.525
General function:
Involved in carboxylesterase activity
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
Molecular weight:
68417.575
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1B
Uniprot ID:
Q9Y5K3
Molecular weight:
40228.99
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
Molecular weight:
41730.67
General function:
Cell wall/membrane/envelope biogenesis
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
Molecular weight:
45270.99
General function:
Cell wall/membrane/envelope biogenesis
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
Molecular weight:
52248.53

Transporters

General function:
Involved in choline transmembrane transporter activity
Specific function:
Choline transporter. May be involved in membrane synthesis and myelin production.
Gene Name:
SLC44A1
Uniprot ID:
Q8WWI5
Molecular weight:
73301.28
General function:
Involved in transporter 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
Molecular weight:
63202.985
General function:
Involved in ion 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, 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
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
General function:
Not Available
Specific function:
Not Available
Gene Name:
SLC44A4
Uniprot ID:
Q53GD3
Molecular weight:
74503.595
General function:
Involved in choline transmembrane transporter activity
Specific function:
Isoform 1, but not isoform 3, exhibits some choline transporter activity.
Gene Name:
SLC44A2
Uniprot ID:
Q8IWA5
Molecular weight:
79845.355
General function:
Not Available
Specific function:
Not Available
Gene Name:
SLC44A3
Uniprot ID:
Q8N4M1
Molecular weight:
73782.63

Only showing the first 10 proteins. There are 42 proteins in total.