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Record Information
Version4.0
Creation Date2009-11-30 15:50:13 UTC
Update Date2017-09-27 08:27:13 UTC
HMDB IDHMDB0013162
Secondary Accession Numbers
  • HMDB13162
Metabolite Identification
Common Name2-Hexenoylcholine
Description2-Hexenoylcholine is a fatty acid-choline as the ester product of 2-Hexenoic acid and cholinel. The pharmacological effects of a series of fatty acid-choline esters have been studied on the isolated rabbit heart, the isolated guinea-pig ileum and the rat stomach. The effect changed with increasing chain length, and three different types of response were observed. The shortchain compounds produced depression of the isolated rabbit heart and spasm of the isolated guinea-pig ileum. Only one, butyrylcholine, had an erratic stimulating effect on hydrochloric acid secretion by the partially vagotomized rat stomach. Medium-chain compounds had a stimulating effect on the isolated rabbit heart, a mixed spasmogenic and relaxant effect on the isolated guinea-pig ileum, and no effect on the rat stomach. Long-chain compounds blocked the effect of acetylcholine on the isolated rabbit heart and the isolated guinea-pig ileum; they also depressed spontaneous hydrochloric acid secretion by the rat stomach.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H22NO2
Average Molecular Weight200.2979
Monoisotopic Molecular Weight200.165053953
IUPAC Name{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium
Traditional Name{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium
CAS Registry NumberNot Available
SMILES
CCC\C=C\C(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C11H22NO2/c1-5-6-7-8-11(13)14-10-9-12(2,3)4/h7-8H,5-6,9-10H2,1-4H3/q+1/b8-7+
InChI KeyFEBXWAFFYJZFMS-BQYQJAHWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Fatty acyl
  • Tetraalkylammonium salt
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic salt
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP-1.9ALOGPS
logP-2ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity70.87 m³·mol⁻¹ChemAxon
Polarizability23.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029317
KNApSAcK IDNot Available
Chemspider ID14582873
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22155829
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available