Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:50:59 UTC
Update Date2020-02-26 21:38:20 UTC
HMDB IDHMDB0013208
Secondary Accession Numbers
  • HMDB13208
Metabolite Identification
Common Name9-Hexadecenoylcholine
Description9-Hexadecenoylcholine, also known as palmitoloelycholine, is a fatty acid-choline and is the ester product of 9-hexadecenoic acid and choline. 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 short-chain 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
Data?1582753100
Synonyms
ValueSource
Choline palmitoleateHMDB
PalmitoloelycholineHMDB
9-HexadecenoylcholineHMDB
Chemical FormulaC21H42NO2
Average Molecular Weight340.571
Monoisotopic Molecular Weight340.321006017
IUPAC Name{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium
Traditional Name{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium
CAS Registry Number943438-47-9
SMILES
CCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C21H42NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)24-20-19-22(2,3)4/h10-11H,5-9,12-20H2,1-4H3/q+1/b11-10-
InChI KeyKZSMYKYPFGHWQV-KHPPLWFESA-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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility1.2e-05 g/LALOGPS
logP2.58ALOGPS
logP1.9ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity116.9 m³·mol⁻¹ChemAxon
Polarizability44.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+190.94230932474
DeepCCS[M-H]-188.39130932474
DeepCCS[M-2H]-221.59230932474
DeepCCS[M+Na]+197.28530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2620.3Standard polar33892256
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2106.4Standard non polar33892256
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2338.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-Hexadecenoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Hexadecenoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
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 IDFDB029334
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]