Record Information
Version1.0
Creation date2011-09-21 01:25:57 UTC
Update date2018-05-28 18:37:56 UTC
Primary IDFDB027530
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(14:0)
DescriptionLysoPC(14:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. 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(14:0), in particular, consists of one chain of myristic acid at the C-1 position. The myristic acid moiety is derived from nutmeg and butter. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. [HMDB]
CAS Number20559-16-4
Structure
Thumb
Synonyms
SynonymSource
1-C14:0-Lysophosphatidylcholine betaineChEBI
1-Myristoyl-glycero-3-phosphocholineChEBI
1-Myristoyl-sn-glycero-3-phosphocholine betaineChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholineChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine betaineChEBI
LPC(14:0)ChEBI
LPC(14:0/0:0)ChEBI
LyPC(14:0)ChEBI
LyPC(14:0/0:0)ChEBI
Lysophosphatidylcholine(14:0/0:0)ChEBI
PC(14:0/0:0)ChEBI
LysoPC(14:0/0:0)Lipid Annotator, ChEBI
Lysophosphatidylcholine(14:0)Lipid Annotator, HMDB
1-tetradecanoyl-glycero-3-phosphocholineLipid Annotator, HMDB
LysoPC(14:0)Lipid Annotator, HMDB
1-MyristoylglycerophosphocholineHMDB
1-TetradecanoylglycerophosphocholineHMDB
1-Myristoyl-GPCHMDB
1-Myristoyl-lysophosphatidylcholineHMDB
1-Myristoyl-sn-glycero-3-phosphocholineHMDB
GPC(14:0)HMDB
GPC(14:0/0:0)HMDB
1-Myristoyl-glycero-3-ocholineChEBI
1-myristoyl-glycero-3-phosphocholinehmdb
1-Tetradecanoyl-sn-glycero-3-ocholineChEBI
Lysoatidylcholine(14:0)HMDB
Lysoatidylcholine(14:0/0:0)ChEBI
LysoPC a C14:0HMDB
Predicted Properties
PropertyValueSource
Water Solubility0.00075 g/LALOGPS
logP1.1ALOGPS
logP0.3ChemAxon
logS-5.8ALOGPS
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 Count22ChemAxon
Refractivity133.07 m³·mol⁻¹ChemAxon
Polarizability53.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H46NO7P
IUPAC name(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1
InChI KeyVXUOFDJKYGDUJI-OAQYLSRUSA-N
Isomeric SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight467.5769
Monoisotopic Molecular Weight467.301189343
Classification
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 effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(14:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0230-9411000000-7a6b8e8fd1e0609b417eSpectrum
Predicted GC-MSLysoPC(14:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLysoPC(14:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-c557e23aa67a6a68e471Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000900000-89cc0e21e01554e310d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1617900000-231c7760e10f0c81e04bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000390000-b1814b140293d64c3417Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090160000-48fcbf8694eed693a211Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090110000-c40c1368f5389cd115f2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000900000-534f405ea851fa87d3e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900600000-9a2a86225de12cddb6bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910400000-63d03888aa82a44da515Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030900000-648928c7aa526a1c5514Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090100000-6eecefd72f10fda6c57aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-aaa1334bcdf77ff34dd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-56c0d0685c46c9ba6fe3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01i0-0010900000-50babd7089582cb56ec8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0390400000-26a01ba41c58e985ad7cSpectrum
NMRNot Available
ChemSpider ID405289
ChEMBL IDCHEMBL462723
KEGG Compound IDC04230
Pubchem Compound ID460604
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10379
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
60 kDa lysophospholipaseASPGQ86U10
Eosinophil lysophospholipaseCLCQ05315
Platelet-activating factor acetylhydrolasePLA2G7Q13093
Platelet-activating factor acetylhydrolase IB subunit gammaPAFAH1B3Q15102
Platelet-activating factor acetylhydrolase IB subunit betaPAFAH1B2P68402
Platelet-activating factor acetylhydrolase 2, cytoplasmicPAFAH2Q99487
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference