Record Information
Version1.0
Creation Date2016-10-03 18:13:38 UTC
Update Date2020-04-22 15:42:56 UTC
BMDB IDBMDB0011149
Secondary Accession Numbers
  • BMDB11149
Metabolite Identification
Common NameLysoPC(O-18:0)
DescriptionLysoPC(O-18:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(O-18:0/0:0), in particular, consists of one octadecyl chain to the C-1 atom, and one octadecyl to the C-2 atom. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
Synonyms
ValueSource
1-O-Octadecylglycerol-3-phosphatidylcholineHMDB
1-Octadecyl-sn-glycero-3-phosphocholineHMDB
1-Stearyl-GPCHMDB
1-Stearyl-GPC (O-18:0)HMDB
GPC(O-18:0)HMDB
GPC(O-18:0/0:0)HMDB
LPC (O-18:0)HMDB
LysoPC(18:0E/0:0)HMDB
LysoPC(O-18:0)HMDB
PC(O-18:0/0:0)HMDB
LysoPC(DM18:0)HMDB
1-O-Octadecyl-sn-glycero-3-phosphocholineHMDB
1-O-Octadecyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Octadecyl-GPCHMDB
1-Octadecyl-lysophosphatidylcholineHMDB
1-Octadecylglycero-3-phosphocholineHMDB
GPC(18:0)HMDB
GPC(18:0/0:0)HMDB
LPC(18:0)HMDB
LPC(18:0/0:0)HMDB
LPC(O-18:0)HMDB
LPC(O-18:0/0:0)HMDB
Lyso-platelet-activating factorHMDB
LysoPC(18:0)HMDB
LysoPC(18:0/0:0)HMDB
Lysophosphatidylcholine(18:0)HMDB
Lysophosphatidylcholine(18:0/0:0)HMDB
Lysophosphatidylcholine(O-18:0)HMDB
Lysophosphatidylcholine(O-18:0/0:0)HMDB
LysoPC(O-18:0/0:0)HMDB
Chemical FormulaC26H56NO6P
Average Molecular Weight509.6997
Monoisotopic Molecular Weight509.384525041
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1
InChI KeyXKBJVQHMEXMFDZ-AREMUKBSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentMonoalkylglycerophosphocholines
Alternative Parents
Substituents
  • Monoalkylglycerophosphocholine
  • Phosphocholine
  • Glycerol ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.98ALOGPS
logP2.46ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.05 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.72 m³·mol⁻¹ChemAxon
Polarizability62.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-5930000000-c002f9346ff27ec388a3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9460000000-f8bf856a15fd2cd2fa22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9123230000-9e5018d60ea3b2b28b32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ugr-9455200000-0c72dc03f55ca1a4599eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-9231000000-adbce76401a5b20f74d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0010490000-78228db3f0e06f9d298cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar0-2160920000-56a3704799b8868294e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9280000000-a127711d12f38e903413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-92389686f000bb55e113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000090000-92389686f000bb55e113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000930000-3fa7cb0f3d40c52c6b6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-0092c5cfc59f1e835b62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0020290000-1cacf188cd006762529aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210100000-3e2f6987fc891e79e2c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-ac3949a1bc7527be80e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0110690000-b1a4faf5ff77d30fbafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0110910000-2f268286db3bc04e9cecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il0-1900160000-4dc04f9d727b989bed34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1710190000-87893f3898856e238cebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ik9-0710190000-487f87885e45a61ac64dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011149
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027924
KNApSAcK IDNot Available
Chemspider ID2015318
KEGG Compound IDC04317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2733532
PDB IDNot Available
ChEBI ID75216
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available