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Record Information
StatusDetected and Quantified
Creation Date2008-09-12 01:28:30 UTC
Update Date2021-09-14 15:41:55 UTC
Secondary Accession Numbers
  • HMDB07930
Metabolite Identification
Common NamePC(14:1(9Z)/P-18:1(11Z))
DescriptionPC(14:1(9Z)/P-18:1(11Z)) 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(14:1(9Z)/P-18:1(11Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
GlycerophosphocholineMetBuilder, HMDB
1-(9Z-Tetradecenoyl)-2-(1Z,11Z-octadecadienyl)-sn-glycero-3-phosphocholineMetBuilder, HMDB
Glycerophosphocholine(14:1(9Z)/p-18:1(11Z))MetBuilder, HMDB
PC(14:2)MetBuilder, HMDB
gpcho(14:2)MetBuilder, HMDB
Phosphatidylcholine(14:2)MetBuilder, HMDB
PC(14:1/P-18:1)MetBuilder, HMDB
gpcho(14:1/P-18:1)MetBuilder, HMDB
Phosphatidylcholine(14:1/p-18:1)MetBuilder, HMDB
Chemical FormulaC40H76NO7P
Average Molecular Weight714.0077
Monoisotopic Molecular Weight713.535940303
IUPAC Nametrimethyl[2-({2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato}oxy)ethyl]azanium
Traditional Namelecithin
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycerophosphocholines
Direct Parent1-acyl,2-(1Z-alkenyl)-glycerophosphocholines
Alternative Parents
  • 1-acyl,2-(1z-alkenyl)-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

Biological location


Route of exposure

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility3.0e-05 g/LALOGPS
logP10(5.52) g/LALOGPS
logP10(7.78) g/LChemAxon
logS10(-7.4) g/LALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity218.44 m³·mol⁻¹ChemAxon
Polarizability87.51 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices


MetaboliteSMILESKovats RI ValueColumn TypeReference
PC(14:1(9Z)/P-18:1(11Z))CCCCCC\C=C/CCCCCCCC\C=C/OC(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C4937.9Standard polar33892256
PC(14:1(9Z)/P-18:1(11Z))CCCCCC\C=C/CCCCCCCC\C=C/OC(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C4093.3Standard non polar33892256
PC(14:1(9Z)/P-18:1(11Z))CCCCCC\C=C/CCCCCCCC\C=C/OC(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C4664.3Semi standard non polar33892256
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • All Tissues
Normal Concentrations
BloodDetected and Quantified4.02 +/- 1.47 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.34 (1.65-3.14) uMInfant (0-1 year old)Not Available
BloodDetected and Quantified5.75(3.77) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.66 (0.48-0.92) uMNewborn (0-30 days old)Not Available
FecesDetected and Quantified0.03 +/- 0.02 nmol/g wet fecesAdult (>18 years old)Both
FecesDetected and Quantified0.06 +/- 0.05 nmol/g wet fecesAdult (>18 years old)Both
Abnormal Concentrations
BloodDetected and Quantified4.08(1.91) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified3.88(2.09) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified3.395 (3.2336) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified6.5874 (2.6463) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified3.02 +/- 1.66 uMChildren (1-13 years old)Both
    • Metabolomics reve...
BloodDetected and Quantified3.99 +/- 1.62 uMChildren (1-13 years old)Both
    • Metabolomics reve...
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood1.375 +/- 0.950 uMAdult (>18 years old)BothNormal (Upper Limit)Concentration data updated from parsing Nick's...
Blood0.000 +/- 0.000 uMAdult (>18 years old)BothNormal (Most Probable)Concentration data updated from parsing Nick's...
Associated Disorders and Diseases
Disease References
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766606
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478643
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000524
Good Scents IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 78 proteins in total.


General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
Uniprot ID:
Molecular weight:


General function:
Involved in ATP binding
Specific function:
Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:
Uniprot ID:
Molecular weight:

Only showing the first 10 proteins. There are 78 proteins in total.