PC(14:1(9Z)/18:1(11Z)) (YMDB13621)

Identification
YMDB IDYMDB13621
NamePC(14:1(9Z)/18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(14:1(9Z)/18:1(11Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(14:1(9Z)/18:1(11Z)), in particular, consists of one 9Z-tetradecenoyl chain to the C-1 atom, and one 11Z-octadecenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Phosphatidylcholine(14:1/18:1)
  • 1-myristoleoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(32:2)
  • GPCho(14:1/18:1)
  • PC(14:1(9Z)/18:1(11Z))
  • PC(14:1/18:1)
  • GPCho(32:2)
  • Lecithin
  • 1-(9Z-tetradecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • PC(32:2)
CAS numberNot Available
WeightAverage: 730.0071
Monoisotopic: 729.530854925
InChI KeyQNWUSMHOBHFMNS-MIXVWNHBSA-N
InChIInChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h13,15-16,18,38H,6-12,14,17,19-37H2,1-5H3/b15-13-,18-16-/t38-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphono]oxy}ethyl)azanium
Traditional IUPAC Nametrimethyl(2-{[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphono]oxy}ethyl)azanium
Chemical FormulaC40H76NO8P
SMILESCCCCCC\C=C/CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP5.12ALOGPS
logP7.39ChemAxon
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 Count38ChemAxon
Refractivity218.1 m³·mol⁻¹ChemAxon
Polarizability87.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Phosphatidylcholine biosynthesis PC(14:1(9Z)/18:1(11Z))PW002865 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-2c3238d389cac738936fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-36b81a67e325f0216f8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-92869ee21f554b869f89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-144e898f8b56e36bfc48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-647bb30a36b4a684d60bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900231200-612bcf5c3de3cb16dcb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-2059ce0696da48a2a005JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000001900-e61844da3e6ca3967d64JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0600491100-c4a23e6a2dd935e99d65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-76332e6fc80373c2f62dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000900-0ebd7f298131a1b0d4b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ji-0090000400-f9dd1322efb28ef00ca3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-5f02b9487b48f138b9ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000001900-cf4a5735287140ffe940JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0101491100-d9366216425f06b3a3c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-6a6809008cae91e5f388JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090043800-043e740278f49db630d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3294000000-c06a835bfbe3e2c66ae7JSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0007905
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider ID24766581
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available