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Record Information
Version3.6
Creation Date2009-11-30 15:51:04 UTC
Update Date2013-02-09 00:29:55 UTC
HMDB IDHMDB13213
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-Linoleoylcholine
Descriptionalpha-Linoleoylcholine is a fatty acid-choline as the ester product of alpha-Linoleoic 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 FormulaC23H44NO2
Average Molecular Weight366.601
Monoisotopic Molecular Weight366.337204657
IUPAC Nametrimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium
Traditional Nametrimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C23H44NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)26-22-21-24(2,3)4/h9-10,12-13H,5-8,11,14-22H2,1-4H3/q+1/b10-9-,13-12-
InChI KeyFDCFEKFQGUEBOI-UTJQPWESSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassCholines
Other Descriptors
  • Fatty Acid Esters
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Quaternary Ammonium Salt
Direct ParentCholines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 Solubility1.03e-05ALOGPS
logP3.08ALOGPS
logP2.42ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.22 m3·mol-1ChemAxon
Polarizability47.51 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB029337
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13213
Metagene LinkHMDB13213
METLIN IDNot Available
PubChem Compound53481656
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available