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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:06:11 UTC
Update Date2021-09-26 23:15:27 UTC
HMDB IDHMDB0258493
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Lysophosphatidylcholine
Description(2-{[2-hydroxy-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Based on a literature review very few articles have been published on (2-{[2-hydroxy-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-lysophosphatidylcholine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Lysophosphatidylcholine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Stearoyl alpha-lysolecithinMeSH
Stearoyl alpha-lysolecithin, (+-)-isomerMeSH
Stearoyl alpha-lysolecithin, (R)-isomerMeSH
StearoyllysophosphatidylcholineMeSH
Stearoyl L-alpha-lysolecithinMeSH
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholineMeSH
1-Stearoyl-sn-glycero-3-phosphorylcholineMeSH
1-Octadecyl-glycero-3-phosphocholineMeSH
1-OctadecylglycerophosphocholineHMDB
Chemical FormulaC26H54NO7P
Average Molecular Weight523.692
Monoisotopic Molecular Weight523.363790081
IUPAC Name(2-{[2-hydroxy-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[2-hydroxy-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3
InChI KeyIHNKQIMGVNPMTC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
logP2.53ALOGPS
logP2.08ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.48 m³·mol⁻¹ChemAxon
Polarizability63.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+227.41430932474
DeepCCS[M-H]-224.15430932474
DeepCCS[M-2H]-258.68230932474
DeepCCS[M+Na]+234.91130932474
AllCCS[M+H]+240.932859911
AllCCS[M+H-H2O]+239.732859911
AllCCS[M+NH4]+242.032859911
AllCCS[M+Na]+242.332859911
AllCCS[M-H]-234.932859911
AllCCS[M+Na-2H]-237.432859911
AllCCS[M+HCOO]-240.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-LysophosphatidylcholineCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C3564.2Standard polar33892256
2-LysophosphatidylcholineCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C3191.9Standard non polar33892256
2-LysophosphatidylcholineCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C3508.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Lysophosphatidylcholine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Lysophosphatidylcholine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 ID78066
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]