PC(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z)) (YMDB02114)

Identification
YMDB IDYMDB02114
NamePC(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z)) 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(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of homo-g-linolenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The homo-g-linolenic acid moiety is derived from fish oils, liver and kidney, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-homo-g-linolenoyl-2-a-linolenoyl-sn-glycero-3-phosphocholine
  • 1-homo-gamma-linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholine
  • GPCho(20:3/18:3)
  • GPCho(20:3n6/18:3n3)
  • GPCho(20:3w6/18:3w3)
  • GPCho(38:6)
  • Lecithin
  • PC(20:3/18:3)
  • PC(20:3n6/18:3n3)
  • PC(20:3w6/18:3w3)
  • Phosphatidylcholine(20:3/18:3)
  • Phosphatidylcholine(20:3n6/18:3n3)
  • Phosphatidylcholine(20:3w6/18:3w3)
  • Phosphatidylcholine(38:6)
  • PC(38:6)
  • 1-Homo-g-linolenoyl-2-a-linolenoyl-sn-glycero-3-phosphocholine
  • GPCho(38:6)
  • Phosphatidylcholine(20:3/18:3)
  • PC(20:3/18:3)
  • Phosphatidylcholine(38:6)
  • Lecithin
  • GPCho(20:3/18:3)
  • 1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholine
  • PC(20:3(8Z,11Z,14Z)/18:3(9Z,12Z,15Z))
CAS numberNot Available
WeightAverage: 806.1031
Monoisotopic: 805.562155053
InChI KeyONHNZXQSGXKTJD-USYZEHPZSA-N
InChIInChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h9,11,14-17,20-22,24-26,44H,6-8,10,12-13,18-19,23,27-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC46H80NO8P
SMILESCCCCCC=CCC=CCC=CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC
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 Solubility3.1e-05 g/LALOGPS
logP5.7ALOGPS
logP8.61ChemAxon
logS-7.4ALOGPS
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
Refractivity250.17 m³·mol⁻¹ChemAxon
Polarizability95.45 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
0.557 ± 0.02785 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8091041220-a223b81793292ed7cf9aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4191021100-ef3f4d28ba76990c5b11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-9085004000-c54a5c375bb6057a4d0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbi-0095000040-9e759982121a1c30693eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0097000200-f6fbae4b2a1553faf7b3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4092000000-3c265b78dc888c77b6bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-1e78e28c2730b5262b1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-f42482894aa2a9df4b6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0200498220-bed1e8ca6df5d95ed732JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6dad79f01b1173c5421fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0074004390-eb5983baec2fd08b542cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6259000000-65f6ac8f19a4714e9737JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-489803391fb15e1d23f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-e0c7549473f8627cae46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-090a85973689c73b02b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-8b00eebc929d9a9097dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-71d714a518c51ee5a089JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-4fcca559e523ce31c68bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-16b357af2387839179b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-a90ad92fa7f31896965fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0099000090-e6fbd96b53f6230754d9JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89289
HMDB IDHMDB08404
Pubchem Compound ID52923239
Kegg IDC00157
ChemSpider ID24767064
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available