PC(18:1(11Z)/20:3(5Z,8Z,11Z)) (YMDB01918)

Identification
YMDB IDYMDB01918
NamePC(18:1(11Z)/20:3(5Z,8Z,11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:1(11Z)/20:3(5Z,8Z,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(18:1(11Z)/20:3(5Z,8Z,11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of mead acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the mead acid moiety is derived from fish oils, 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-vaccenoyl-2-meadoyl-sn-glycero-3-phosphocholine
  • GPCho(18:1/20:3)
  • GPCho(18:1n7/20:3n9)
  • GPCho(18:1w7/20:3w9)
  • GPCho(38:4)
  • Lecithin
  • PC(18:1/20:3)
  • PC(18:1n7/20:3n9)
  • PC(18:1w7/20:3w9)
  • PC(38:4)
  • Phosphatidylcholine(18:1n7/20:3n9)
  • Phosphatidylcholine(18:1w7/20:3w9)
  • Phosphatidylcholine(38:4)
  • Phosphatidylcholine(18:1/20:3)
  • PC(38:4)
  • GPCho(38:4)
  • Phosphatidylcholine(38:4)
  • Lecithin
  • PC(18:1/20:3)
  • GPCho(18:1/20:3)
  • 1-Vaccenoyl-2-meadoyl-sn-glycero-3-phosphocholine
  • 1-(11Z-Octadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine
  • PC(18:1(11Z)/20:3(5Z,8Z,11Z))
CAS numberNot Available
WeightAverage: 810.1348
Monoisotopic: 809.593455181
InChI KeyGUKWLDDRYZDHHJ-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/h17,19-20,22,25,27,31,33,44H,6-16,18,21,23-24,26,28-30,32,34-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC46H84NO8P
SMILESCCCCCCCCC=CCC=CCC=CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
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 Solubility2.8e-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
Polarizability99 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, Positivesplash10-000i-8092041220-eb7798121c0df373d802JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3192011100-a61423848287eb3d0e00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7094003200-3c5f52a4ad724f779014JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu0-0092000030-5d8be3df13beddfc91f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0090000100-00c3220b02f9c9f5d774JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bwl-4092000000-fc44643b7797cdd73d4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-fa334b794ce842b59d7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0064004390-c06c0442899cea3cb2eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-6196600000-044931b8ba6ecf1542a5JSpectraViewer
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-e67261bf68dc2911c7c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a66-0099000090-5064bc3e9def2c9b456eJSpectraViewer
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-f4d30f4e0d22520abfd7JSpectraViewer
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, Positivesplash10-0f89-1900041210-8d93219b187c5ee18f89JSpectraViewer
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-b802dd73ad3017d2dc20JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89690
HMDB IDHMDB08079
Pubchem Compound ID53478737
Kegg IDC00157
ChemSpider ID24766743
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available