Identification
YMDB IDYMDB01845
NamePC(16:0/18:2(9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:0/18:2(9Z,12Z)) 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(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed 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.
Structure
Thumb
Synonyms
  • 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • GPCho(16:0/18:2)
  • GPCho(16:0/18:2n6)
  • GPCho(16:0/18:2w6)
  • GPCho(34:2)
  • Lecithin
  • PC(16:0/18:2)
  • PC(16:0/18:2w6)
  • PC(34:2)
  • Phosphatidylcholine(16:0/18:2)
  • Phosphatidylcholine(16:0/18:2n6)
  • Phosphatidylcholine(16:0/18:2w6)
  • Phosphatidylcholine(34:2)
  • PC(16:0/18:2n6)
  • 1-Palmitoyl-2-linoleoyl-GPC
  • 1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2)
  • 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
  • 1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine
  • 1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholine
  • 1-Palmitoyl-2-linoleoylphosphatidylcholine
  • GPC(16:0/18:2)
  • GPCho 16:0/18:2(9Z,12Z)
  • GPCho(16:0/18:2(9Z,12Z))
  • GPCho(16:0/18:2)
  • GPCho(16:0/18:2omega6)
  • Lecithin
  • PC 16:0/18:2(9Z,12Z)
  • PC(16:0/18:2)
  • PC(16:0/18:2omega6)
  • PC(34:2)
  • Phosphatidylcholine 16:0/18:2(9Z,12Z)
  • Phosphatidylcholine(16:0/18:2(9Z,12Z))
  • Phosphatidylcholine(16:0/18:2)
  • Phosphatidylcholine(16:0/18:2omega6)
  • Gpcho(34:2)
  • Phosphatidylcholine(34:2)
  • 2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholine
  • Palmitoyl-linoleoatephosphatidylcholine
  • PLPC
  • 1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
  • 1-Palmitoyl-2-linoleoyl-3-phosphatidylcholine
  • 1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholine
  • 1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine
  • 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine
  • 1-Palmitoyl-2-linoleoyllecithin
  • GPC(16:0/18:2(9Z,12Z))
  • GPC(16:0/18:2n6)
  • GPC(16:0/18:2W6)
  • GPC(34:2)
  • GPCho(16:0/18:2n6)
  • GPCho(16:0/18:2W6)
  • L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholine
  • L-Α-1-palmitoyl-2-linoleoylphosphatidylcholine
  • PC(16:0/18:2W6)
  • Phosphatidylcholine(16:0/18:2n6)
  • Phosphatidylcholine(16:0/18:2W6)
  • PC(16:0/18:2(9Z,12Z))
CAS numberNot Available
WeightAverage: 758.0603
Monoisotopic: 757.562155053
InChI KeyJLPULHDHAOZNQI-RRHRGVEJSA-N
InChIInChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/t40-/m1/s1
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC42H80NO8P
SMILESCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC
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
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • 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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.5e-05 g/LALOGPS
logP5.48ALOGPS
logP8.28ChemAxon
logS-7.5ALOGPS
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 Count40ChemAxon
Refractivity227.3 m³·mol⁻¹ChemAxon
Polarizability92.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
3 ± 0 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-b7304b809294dbb2ea74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0006-0000000940-6acae25b185d1a864052JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-537e946aca08f069e72bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-002f-0090000700-ecca901df00a9bff124cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-0090000200-fa34aef5028ed4787c4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-0090000000-d9440bc0e6a9f6cdaf65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-004i-0090000000-a5231d807bde53ae849aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, negativesplash10-056r-0090000000-23038428933dc1fcc66dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-056r-0090000000-ccce70356f7c7b18cbbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-056r-1090000000-32df8fc00b6e170aa02aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-004i-7190000000-811ed3f1fe9d51baf806JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 193V, negativesplash10-004i-9000000000-4bd8d3812cfdbafe42c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-aed1ee56f1886685cef5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-f70fecaaa4c193d6952dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-40ddf52a50eed646c5c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-79413b6bfab2c2699ebbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-0006-0020000900-30d6507c6252bceda2abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, negativesplash10-002f-0090000800-e35e5d8e6ef65358f1d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-004i-0090000200-d82c61ca09093ce2f75aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, negativesplash10-004i-0090000000-a788f61f6153073cc513JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-056r-0090000000-5242b45696e3aa936e70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 89V, negativesplash10-056r-0090000000-23038428933dc1fcc66dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-73b8731f1bdde398585fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-37c5a628d36a084e1386JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900231200-522c9f77a95c208b08bcJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID73002
HMDB IDHMDB07973
Pubchem Compound ID5287971
Kegg IDC00157
ChemSpider ID24822352
FOODB IDFDB030253
Wikipedia IDNot Available
BioCyc IDNot Available