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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:51:15 UTC
Update Date2020-04-30 16:28:36 UTC
HMDB IDHMDB0013223
Secondary Accession Numbers
  • HMDB13223
Metabolite Identification
Common NameButyrylcholine
DescriptionButyrylcholine belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Butyrylcholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyrylcholine is a synthetic compound and does not occur in the body naturally. It is used as a tool to distinguish between acetyl- and butyrylcholinesterase. Butyrylcholine is an acetylcholine-like molecule, with activation of some of the same receptors as acetylcholine. It is hydrolyzed by acetylcholinesterase and butyrylcholinesterase (also known as pseudocholinesterase), with butyrylcholinesterase being more efficient than acetylcholinesterase. Butyrylcholine is a nicotinic receptor agonist and mimics the action of acetylcholine (ACh) at both enteric and epithelial nicotinic acetylcholine receptors (nAChRs). Additionally, butyrylcholine is also able to stimulate muscarinic acetylcholine receptors (mAChRs) (PMID: 6481626 , 27423041 ).
Structure
Data?1588262738
Synonyms
ValueSource
(2-Butyryloxy-ethyl)-trimethyl-ammoniumHMDB
N,N,N-Trimethyl-2-(1-oxobutoxy)ethanaminiumHMDB
ButyrylcholineHMDB
Chemical FormulaC9H20NO2
Average Molecular Weight174.2606
Monoisotopic Molecular Weight174.149403889
IUPAC Name[2-(butanoyloxy)ethyl]trimethylazanium
Traditional Namebutyrylcholine
CAS Registry Number3922-86-9
SMILES
CCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1
InChI KeyYRIBGSCJIMXMPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.57 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+136.25130932474
DeepCCS[M-H]-133.65930932474
DeepCCS[M-2H]-169.65930932474
DeepCCS[M+Na]+144.5330932474
AllCCS[M+H]+141.232859911
AllCCS[M+H-H2O]+137.732859911
AllCCS[M+NH4]+144.632859911
AllCCS[M+Na]+145.532859911
AllCCS[M-H]-151.832859911
AllCCS[M+Na-2H]-153.532859911
AllCCS[M+HCOO]-155.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButyrylcholineCCCC(=O)OCC[N+](C)(C)C1440.6Standard polar33892256
ButyrylcholineCCCC(=O)OCC[N+](C)(C)C987.0Standard non polar33892256
ButyrylcholineCCCC(=O)OCC[N+](C)(C)C1161.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Butyrylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyrylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029342
KNApSAcK IDNot Available
Chemspider ID16312
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyrylcholine
METLIN IDNot Available
PubChem Compound17233
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Andreev AA, Veprintsev BN, Vulfius CA: Two-component desensitization of nicotinic receptors induced by acetylcholine agonists in Lymnaea stagnalis neurones. J Physiol. 1984 Aug;353:375-91. doi: 10.1113/jphysiol.1984.sp015341. [PubMed:6481626 ]
  2. Moreno S, Gerbig S, Schulz S, Spengler B, Diener M, Bader S: Epithelial propionyl- and butyrylcholine as novel regulators of colonic ion transport. Br J Pharmacol. 2016 Sep;173(18):2766-79. doi: 10.1111/bph.13555. Epub 2016 Aug 10. [PubMed:27423041 ]