PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (YMDB02063)

Identification
YMDB IDYMDB02063
NamePC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:1(11Z)/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(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicosenoic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The eicosenoic acid moiety is derived from vegetable oils and cod oils, 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-eicosenoyl-2-eicsoate
  • 1-eicosenoyl-2-eicsoic acid
  • GPCho(20:1/20:4)
  • GPCho(20:1n9/20:4n3)
  • GPCho(20:1w9/20:4w3)
  • GPCho(40:5)
  • Lecithin
  • PC(20:1/20:4)
  • PC(20:1n9/20:4n3)
  • PC(20:1w9/20:4w3)
  • PC(40:5)
  • Phosphatidylcholine(20:1/20:4)
  • Phosphatidylcholine(20:1n9/20:4n3)
  • Phosphatidylcholine(20:1w9/20:4w3)
  • Phosphatidylcholine(40:5)
  • 1-eicosenoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(40:5)
  • PC(20:1/20:4)
  • GPCho(20:1/20:4)
  • GPCho(40:5)
  • Phosphatidylcholine(20:1/20:4)
  • Lecithin
  • PC(40:5)
  • 1-(11-Eicosenoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine
  • PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))
CAS numberNot Available
WeightAverage: 836.1721
Monoisotopic: 835.609105245
InChI KeySFSJJONFWFZOGW-YACUFSJGSA-N
InChIInChI=1S/C48H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,20-23,27,29,46H,6-8,10,12-14,16,18-19,24-26,28,30-45H2,1-5H3/t46-/m1/s1
IUPAC Name(2-{[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC48H86NO8P
SMILESCCCCCCCCC=CCCCCCCCCCC(=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 Solubility2.8e-05 g/LALOGPS
logP6.27ALOGPS
logP9.86ChemAxon
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 Count43ChemAxon
Refractivity258.26 m³·mol⁻¹ChemAxon
Polarizability101.96 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
0.098 ± 0.0049 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-0000000090-e8fe727b896a8f0e45ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-977a0aae3871af3fddf5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-343b58f4113321642374JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-e44e17bc1f6f02d38f6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-7b576ef6c884f4d108d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0900369110-b3382be60410eb17ef94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-15b2ef6ef5599be4c310JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0003000090-d939b7a2bb0a40e845f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-14vi-0009000040-992fcb51db4d267964a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-48ed3e78edc4580cc5c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000190-e895b127f03481afc6e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200498220-8fc1e4ad6e66c5426ed2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-f24f77194ba43a429ea3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0029003370-dbd82373c5191accb2b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6049000000-d65420235913ba2f6f44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-94e5270a0f467faa7605JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000090-81bf88f117f9e08f9d21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041120-4e234ec9ac8272b2c086JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB08313
Pubchem Compound ID53478899
Kegg IDC00157
ChemSpider ID24766974
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available