PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (YMDB01877)

Identification
YMDB IDYMDB01877
NamePC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:1(9Z)/20:5(5Z,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(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the eicosapentaenoic 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-palmitoleoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine
  • GPCho(16:1/20:5)
  • GPCho(16:1n7/20:5n3)
  • GPCho(36:6)
  • Lecithin
  • PC(16:1/20:5)
  • PC(16:1n7/20:5n3)
  • PC(16:1w7/20:5w3)
  • PC(36:6)
  • Phosphatidylcholine(16:1/20:5)
  • Phosphatidylcholine(16:1n7/20:5n3)
  • Phosphatidylcholine(16:1w7/20:5w3)
  • Phosphatidylcholine(36:6)
  • GPCho(16:1w7/20:5w3)
  • PC(16:1/20:5)
  • GPCho(16:1/20:5)
  • GPCho(36:6)
  • 1-Palmitoleoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine
  • Lecithin
  • PC(36:6)
  • Phosphatidylcholine(16:1/20:5)
  • 1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(36:6)
  • PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))
CAS numberNot Available
WeightAverage: 778.0499
Monoisotopic: 777.530854925
InChI KeyIITWSVMUNFGFQI-HUESYALOSA-N
InChIInChI=1S/C44H76NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h8,10,14,16-17,19-21,23,25,29,31,42H,6-7,9,11-13,15,18,22,24,26-28,30,32-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H76NO8P
SMILESCCCCCCC=CCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC=CCC=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 Solubility3.3e-05 g/LALOGPS
logP5.4ALOGPS
logP7.72ChemAxon
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
Refractivity240.97 m³·mol⁻¹ChemAxon
Polarizability91.28 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
0.021 ± 0.00105 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, Positivesplash10-004i-0000000900-d952f38d42ad6ddf6054JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-c704be0a3ccac58b5732JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-51b10f425373e7a76e5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-0092000300-281d6b4ee7b6b5db2a03JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090001000-4afb40e0fd8710fdab4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-4092000000-712e6ecc05b5f1067029JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-41c33084af9f783c847dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-dd151cc7bd543b751825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0200669400-8bd41403b444f4938a28JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-e97180150486da753e49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-cd910875d8659ad53678JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0900449110-84a47156b3f0d4881387JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-5a1f7e5d648203ccaa08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0053030900-f8a6a6b51561524fa0f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3291000000-9f9e15b7ce5aa3f92896JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e158c1e70dedba30b57eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-259bce635b325b3b4835JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-bae344dcea43b8ff0b76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-87e491c712a61c58fe72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000090-00ac5bf7d774a451f19dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w29-0099000090-341e85ab53fc2ceadb5bJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89739
HMDB IDHMDB08017
Pubchem Compound ID52922465
Kegg IDC00157
ChemSpider ID24766686
FOODB IDFDB025208
Wikipedia IDNot Available
BioCyc IDNot Available