PC(20:3(5Z,8Z,11Z)/18:0) (YMDB02091)

Identification
YMDB IDYMDB02091
NamePC(20:3(5Z,8Z,11Z)/18:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:3(5Z,8Z,11Z)/18:0) 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(5Z,8Z,11Z)/18:0), in particular, consists of one chain of mead acid at the C-1 position and one chain of stearic acid at the C-2 position. The mead acid moiety is derived from fish oils, liver and kidney, while the stearic acid moiety is derived from animal fats, coco butter and sesame 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-meadoyl-2-stearoyl-sn-glycero-3-phosphocholine
  • GPCho(20:3n9/18:0)
  • GPCho(20:3w9/18:0)
  • GPCho(38:3)
  • Lecithin
  • PC(20:3/18:0)
  • PC(20:3n9/18:0)
  • PC(20:3w9/18:0)
  • PC(38:3)
  • Phosphatidylcholine(20:3/18:0)
  • Phosphatidylcholine(20:3n9/18:0)
  • Phosphatidylcholine(20:3w9/18:0)
  • Phosphatidylcholine(38:3)
  • GPCho(20:3/18:0)
  • PC(20:3/18:0)
  • Phosphatidylcholine(38:3)
  • PC(38:3)
  • Lecithin
  • GPCho(38:3)
  • Phosphatidylcholine(20:3/18:0)
  • 1-Meadoyl-2-stearoyl-sn-glycero-3-phosphocholine
  • 1-(5Z,8Z,11Z-Eicosatrienoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine
  • PC(20:3(5Z,8Z,11Z)/18:0)
CAS numberNot Available
WeightAverage: 812.1507
Monoisotopic: 811.609105245
InChI KeyZQCXMBYHCICNPX-USYZEHPZSA-N
InChIInChI=1S/C46H86NO8P/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/h20,22,25-26,30,32,44H,6-19,21,23-24,27-29,31,33-43H2,1-5H3/t44-/m1/s1
IUPAC Name(2-{[(2R)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC46H86NO8P
SMILESCCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCC=CCC=CCC=CCCCCCCCC)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 Solubility2.3e-05 g/LALOGPS
logP6.1ALOGPS
logP9.7ChemAxon
logS-7.6ALOGPS
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
Refractivity246.82 m³·mol⁻¹ChemAxon
Polarizability100.29 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
0.185 ± 0.00925 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-8091041220-21d3291d189c63497c5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3191011100-f829ba4a01cf389b6b2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-8095002200-929b4195c5866bdc27ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu9-0095000040-cd1f9e1502daa5951e96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0098000200-0276d23b86928d29f845JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-4092000000-018d6e1aa24938bc874eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-b1ba273f95f6293d0145JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0011000090-b6715afe99e648d02468JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0099000090-0392a5d79eec0d08f233JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-5cb49c7c039e3d7fca35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-e562dcc8ad422ebb1e79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udk-0900369110-92f4d074ef785d65746eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-6fea64f934a34fc28e70JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0065004390-29bc7fd7866e145c163fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9278500000-08b3c3f2986acf8df451JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-5d09de4c7b02b1d770beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-3e7228ae930b29d5cacbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-5b073d72824ccc2c8072JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-5004d6181bff1df70870JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000190-fc85ca9ecf02ec9d7566JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f80-0200498220-b48732ec4f342347a388JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89111
HMDB IDHMDB08366
Pubchem Compound ID53478953
Kegg IDC00157
ChemSpider ID24767026
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available