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Record Information
Creation date2011-09-21 00:54:49 UTC
Update date2019-11-26 03:21:18 UTC
Primary IDFDB025262
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(18:1(11Z)/18:1(9Z))
DescriptionPC(18:1(11Z)/18:1(9Z)) 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(18:1(11Z)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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. [HMDB]
CAS NumberNot Available
Predicted Properties
Water Solubility2.2e-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 Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability97.1 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC44H84NO8P
IUPAC nametrimethyl(2-{[(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propyl phosphono]oxy}ethyl)azanium
InChI IdentifierInChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16,18,21,23,42H,6-15,17,19-20,22,24-41H2,1-5H3/t42-/m1/s1
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
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 DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
SpectraNot Available
ChemSpider ID24766735
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound ID53478721
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
NameGene NameUniProt ID
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Phospholipase D2PLD2O14939
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Choline kinase alphaCHKAP35790
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Phospholipase D6PLD6Q8N2A8
Lecithin retinol acyltransferaseLRATO95237
Phosphatidylserine synthase 1PTDSS1P48651
Eosinophil lysophospholipaseCLCQ05315
Neuropathy target esterasePNPLA6Q8IY17
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
Phosphatidylethanolamine-binding protein 1PEBP1P30086
Phosphatidylethanolamine-binding protein 4PEBP4Q96S96
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference