PC(18:0/20:4(8Z,11Z,14Z,17Z)) (YMDB01898)

Identification
YMDB IDYMDB01898
NamePC(18:0/20:4(8Z,11Z,14Z,17Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:0/20:4(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(18:0/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-stearoyl-2-eicsoate
  • 1-stearoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine
  • 1-stearoyl-2-eicsoic acid
  • GPCho(18:0/20:4)
  • GPCho(18:0/20:4n3)
  • GPCho(18:0/20:4w3)
  • GPCho(38:4)
  • Lecithin
  • PC(18:0/20:4)
  • PC(18:0/20:4w3)
  • PC(38:4)
  • Phosphatidylcholine(18:0/20:4)
  • Phosphatidylcholine(18:0/20:4n3)
  • Phosphatidylcholine(18:0/20:4w3)
  • Phosphatidylcholine(38:4)
  • PC(18:0/20:4n3)
  • GPCho(18:0/20:4)
  • Phosphatidylcholine(38:4)
  • GPCho(38:4)
  • 1-Stearoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(18:0/20:4)
  • Lecithin
  • PC(18:0/20:4)
  • 1-Octadecanoyl-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine
  • PC(38:4)
  • PC(18:0/20:4(8Z,11Z,14Z,17Z))
CAS numberNot Available
WeightAverage: 810.1348
Monoisotopic: 809.593455181
InChI KeyHAKKEJDMTIQLJH-USYZEHPZSA-N
InChIInChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25,27,44H,6-7,9,11-13,15,17-19,21,23-24,26,28-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC46H84NO8P
SMILESCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC=CCC=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 Solubility2.9e-05 g/LALOGPS
logP6.04ALOGPS
logP9.33ChemAxon
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 Count42ChemAxon
Refractivity247.94 m³·mol⁻¹ChemAxon
Polarizability97.89 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
2 ± 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kur-0092000030-61474b23673fbc43a134JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0090000100-cdd933b4544bbc0819f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kx9-4092000000-2efc3c9f5a2836fea586JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-fa334b794ce842b59d7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0074004390-b1f6964600e3fdee8aceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-6192000000-258aa7e380096a45168dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-20235538cb799e7cb64eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-58feaf75d511d75d6599JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uf6-0099000090-7f1ec3fec9e8c6930b32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8092041220-25f37a9ed631a7240063JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3192011100-e1c4abd6b712cd5a6d7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7094001000-f3b531a726d04287d5ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-12f7c14a559d8169eb4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-4e1c9c4510d5cf1106a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-fe32dc17f26ba414e09eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-b25dca7fc1b5373b3809JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000190-58e0c5d29433cc0e7cdfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0200498220-9ec01b331a44705e5c2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-bd4db731926b5d2cbe56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-c053420ce1420abe1479JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-9ce17a305cd08da2878dJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89672
HMDB IDHMDB08049
Pubchem Compound ID53478701
Kegg IDC00157
ChemSpider ID24766713
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available