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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2020-06-02 21:18:27 UTC
Update Date2022-03-07 03:18:20 UTC
HMDB IDHMDB0240647
Secondary Accession NumbersNone
Metabolite Identification
Common NameDocosahexaenoylcholine
DescriptionDocosahexaenoylcholine, also known as choline docosahexaenoate, 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 Docosahexaenoylcholine.
Structure
Data?1591135768
Synonyms
ValueSource
Choline docosahexaenoateHMDB
Choline docosahexaenoic acidHMDB
DocosahexaenoylcholineHMDB
Chemical FormulaC27H44NO2
Average Molecular Weight414.653
Monoisotopic Molecular Weight414.336656081
IUPAC Name{2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]ethyl}trimethylazanium
Traditional Name{2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]ethyl}trimethylazanium
CAS Registry Number727355-09-1
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C27H44NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27(29)30-26-25-28(2,3)4/h6-7,9-10,12-13,15-16,18-19,21-22H,5,8,11,14,17,20,23-26H2,1-4H3/q+1/b7-6-,10-9-,13-12-,16-15-,19-18-,22-21-
InChI KeyOQLFEDZOXQQFGP-WSDBEMKQSA-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
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • 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
logP3.12ALOGPS
logP2.75ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity150.09 m³·mol⁻¹ChemAxon
Polarizability50.11 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]+221.22930932474
DeepCCS[M-H]-218.87130932474
DeepCCS[M-2H]-251.75630932474
DeepCCS[M+Na]+227.32330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DocosahexaenoylcholineCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCC[N+](C)(C)C3637.6Standard polar33892256
DocosahexaenoylcholineCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCC[N+](C)(C)C2524.6Standard non polar33892256
DocosahexaenoylcholineCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCC[N+](C)(C)C2870.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosahexaenoylcholine 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)BothNormal 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 ID7998856
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9823108
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. Zarei I, Oppel RC, Borresen EC, Brown RJ, Ryan EP: Modulation of plasma and urine metabolome in colorectal cancer survivors consuming rice bran. Integr Food Nutr Metab. 2019 May;6(3). doi: 10.15761/IFNM.1000252. Epub 2019 Apr 5. [PubMed:31396400 ]