PC(18:3(9Z,12Z,15Z)/18:1(11Z)) (YMDB02003)

Identification
YMDB IDYMDB02003
NamePC(18:3(9Z,12Z,15Z)/18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:3(9Z,12Z,15Z)/18:1(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(18:3(9Z,12Z,15Z)/18:1(11Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the vaccenic acid moiety is derived from butter fat and animal fat. 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-alpha-linolenoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
  • GPCho(18:3/18:1)
  • GPCho(18:3n3/18:1n7)
  • GPCho(18:3w3/18:1w7)
  • GPCho(36:4)
  • Lecithin
  • PC(18:3/18:1)
  • PC(18:3n3/18:1n7)
  • PC(18:3w3/18:1w7)
  • PC(36:4)
  • Phosphatidylcholine(18:3/18:1)
  • Phosphatidylcholine(18:3n3/18:1n7)
  • Phosphatidylcholine(18:3w3/18:1w7)
  • Phosphatidylcholine(36:4)
  • 1-a-linolenoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
  • GPCho(36:4)
  • PC(18:3/18:1)
  • Phosphatidylcholine(36:4)
  • GPCho(18:3/18:1)
  • PC(18:3(9Z,12Z,15Z)/18:1(11Z))
  • Lecithin
  • PC(36:4)
  • Phosphatidylcholine(18:3/18:1)
  • 1-(9Z,12Z,15Z-octadeatrienoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine
CAS numberNot Available
WeightAverage: 782.0817
Monoisotopic: 781.562155053
InChI KeyAHEPKIJTHGCAOA-HUESYALOSA-N
InChIInChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8,10,14,16-17,19-20,22,42H,6-7,9,11-13,15,18,21,23-41H2,1-5H3/t42-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Namelecithin
Chemical FormulaC44H80NO8P
SMILESCCCCCCC=CCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=CCC=CCC=CCC)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 Solubility3.2e-05 g/LALOGPS
logP5.68ALOGPS
logP8.44ChemAxon
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
Refractivity238.74 m³·mol⁻¹ChemAxon
Polarizability93.39 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
1 ± 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, Positivesplash10-0fsr-9061061400-61ee6bd749cb293fc772JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u9-5293041100-925f1fa3ca428fd6f64bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9075030100-4b85c87f8cf6a3824857JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090001800-b02f0c7e1da5ea223fc7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090104200-50c04b58628ff46d3ea6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u0-3090100000-0f0527ef30bc4cb5bdd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-08d6fcb41388b1c681f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000090-8399757791cfdf95c0dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0090000040-ea2d30f89ff61b7311bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-3c72155bce4155773a03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-064c081755895a2e4178JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dk-0900369110-4a69111426c2037dbd2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-bc2a7ab6e102186d0c94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-1f8c8c5ddd6d8082b38dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0200498400-a8dc71ebc7b92d614bf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-440a71e9c384cc6f77ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-9035a7e163ecdf01e45fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900050300-d5c624f49dd16e4de5daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2534b1e8e0eb889fbec2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0071030900-f3cd4bf8fadf1d1e57a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3190300000-9d3bcdbc98a63a4ea10cJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB08202
Pubchem Compound ID53478831
Kegg IDC00157
ChemSpider ID24766864
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available