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SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the eicsoatetraenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
  • 1-palmitoleoyl-2-eicsoate
  • 1-palmitoleoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine
  • 1-palmitoleoyl-2-eicsoic acid
  • GPCho(16:1/20:4)
  • GPCho(16:1w7/20:4w3)
  • GPCho(36:5)
  • Lecithin
  • PC(16:1/20:4)
  • PC(16:1n7/20:4n3)
  • PC(16:1w7/20:4w3)
  • PC(36:5)
  • Phosphatidylcholine(16:1/20:4)
  • Phosphatidylcholine(16:1n7/20:4n3)
  • Phosphatidylcholine(16:1w7/20:4w3)
  • Phosphatidylcholine(36:5)
  • GPCho(16:1n7/20:4n3)
  • GPCho(36:5)
  • PC(16:1/20:4)
  • Phosphatidylcholine(36:5)
  • Lecithin
  • PC(36:5)
  • 1-Palmitoleoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(16:1/20:4)
  • 1-(9Z-Hexadecenoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine
  • GPCho(16:1/20:4)
  • PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))
CAS numberNot Available
WeightAverage: 780.0658
Monoisotopic: 779.546504989
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC44H78NO8P
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
Melting pointNot Available
Experimental Properties
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
Water Solubility3.1e-05 g/LALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity239.85 m³·mol⁻¹ChemAxon
Polarizability93.45 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.038 ± 0.0019 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-2292790dcc6329fa8908JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-4b82966448df12be1b8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900230300-569c114c468b9ecf4f05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-0092000300-f86db0f76b9e3714547dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0090001000-a563a7058db3d642ea95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-4092000000-f8115d51c050cfed9bbcJSpectraViewer
References:Not Available
Synthesis Reference:Not Available
External Links:
Pubchem Compound ID53478681
Kegg IDC00157
ChemSpider ID24766685
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available