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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-10-28 16:19:42 UTC
Update Date2022-03-07 03:18:19 UTC
HMDB IDHMDB0240583
Secondary Accession NumbersNone
Metabolite Identification
Common NameArachidonoylcholine
DescriptionArachidonoylcholine, also known as choline arachidonate, 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 a small amount of articles have been published on Arachidonoylcholine.
Structure
Data?1591196218
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-Eicosa-5,8,11,14-tetraenoylcholineChEBI
(5Z,8Z,11Z,14Z)-EicosatetraenoylcholineChEBI
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoylcholineChEBI
(5Z,8Z,11Z,14Z)-IcosatetraenoylcholineChEBI
Choline (5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoateChEBI
Choline (5Z,8Z,11Z,14Z)-eicosatetraenoateChEBI
Choline (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoateChEBI
Choline (5Z,8Z,11Z,14Z)-icosatetraenoateChEBI
Choline arachidonateChEBI
Choline (5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acidGenerator
Choline (5Z,8Z,11Z,14Z)-eicosatetraenoic acidGenerator
Choline (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidGenerator
Choline (5Z,8Z,11Z,14Z)-icosatetraenoic acidGenerator
Choline arachidonic acidGenerator
ArachidonoylcholineHMDB
Chemical FormulaC25H44NO2
Average Molecular Weight390.631
Monoisotopic Molecular Weight390.336656081
IUPAC Name{2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]ethyl}trimethylazanium
Traditional Name{2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]ethyl}trimethylazanium
CAS Registry Number57718-75-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C25H44NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-25(27)28-24-23-26(2,3)4/h9-10,12-13,15-16,18-19H,5-8,11,14,17,20-24H2,1-4H3/q+1/b10-9-,13-12-,16-15-,19-18-
InChI KeyNJSSWIYQGNCVTH-SNPVRQPZSA-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
logP3.14ALOGPS
logP2.59ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity138.66 m³·mol⁻¹ChemAxon
Polarizability49.49 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]+207.30530932474
DeepCCS[M-H]-203.80530932474
DeepCCS[M-2H]-239.81430932474
DeepCCS[M+Na]+216.10530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArachidonoylcholineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC[N+](C)(C)C3258.8Standard polar33892256
ArachidonoylcholineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC[N+](C)(C)C2385.3Standard non polar33892256
ArachidonoylcholineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC[N+](C)(C)C2672.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arachidonoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue Locations
  • Placenta
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 ID58827255
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122198216
PDB IDNot Available
ChEBI ID133694
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 ]
  2. 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 ]