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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2020-06-02 21:47:45 UTC
Update Date2022-03-07 03:18:20 UTC
HMDB IDHMDB0240648
Secondary Accession NumbersNone
Metabolite Identification
Common NameStearoylcholine
Descriptiontrimethyl[2-(octadecanoyloxy)ethyl]azanium, also known as chomelanum, 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. Based on a literature review very few articles have been published on trimethyl[2-(octadecanoyloxy)ethyl]azanium.
Structure
Data?1591134747
Synonyms
ValueSource
ChomelanumKegg
Choline stearic acidGenerator, HMDB
Choline octadecanoateHMDB
Choline octadecanoic acidHMDB
Choline stearateHMDB
N,N,N-Trimethyl-2-[(1-oxooctadecyl)oxy]ethanaminiumHMDB
OctadecanoylcholineHMDB
StearoylcholineHMDB
Chemical FormulaC23H48NO2
Average Molecular Weight370.641
Monoisotopic Molecular Weight370.36795621
IUPAC Nametrimethyl[2-(octadecanoyloxy)ethyl]azanium
Traditional Namecholine stearate
CAS Registry Number23464-76-8
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C23H48NO2/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/h5-22H2,1-4H3/q+1
InChI KeySGFBLYBOTWZDDE-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 DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
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
logP3.7ALOGPS
logP3.15ChemAxon
logS-7.7ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity124.99 m³·mol⁻¹ChemAxon
Polarizability50.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+193.39230932474
DeepCCS[M-H]-190.84230932474
DeepCCS[M-2H]-224.04230932474
DeepCCS[M+Na]+199.73530932474
AllCCS[M+H]+213.132859911
AllCCS[M+H-H2O]+211.032859911
AllCCS[M+NH4]+215.032859911
AllCCS[M+Na]+215.532859911
AllCCS[M-H]-206.932859911
AllCCS[M+Na-2H]-208.832859911
AllCCS[M+HCOO]-211.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
StearoylcholineCCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C2754.7Standard polar33892256
StearoylcholineCCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C2355.6Standard non polar33892256
StearoylcholineCCCCCCCCCCCCCCCCCC(=O)OCC[N+](C)(C)C2567.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Stearoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID81347
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. Germain A, Barupal DK, Levine SM, Hanson MR: Comprehensive Circulatory Metabolomics in ME/CFS Reveals Disrupted Metabolism of Acyl Lipids and Steroids. Metabolites. 2020 Jan 14;10(1). pii: metabo10010034. doi: 10.3390/metabo10010034. [PubMed:31947545 ]