PC(16:0/16:1(9Z)) (YMDB01181)

Identification
YMDB IDYMDB01181
NamePC(16:0/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:0/16:1(9Z)) 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(16:0/16:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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
  • 1-palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
  • 1,2-Diacyl-sn-glycero-3-phosphocholine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-Phosphatidylcholine
  • Choline phosphatide
  • GPCho(16:0/16:1)
  • GPCho(16:0/16:1n7)
  • GPCho(16:0/16:1w7)
  • GPCho(32:1)
  • Lecithin
  • Lecithins
  • O3-Phosphatidyl-L-serine
  • PC(16:0/16:1)
  • PC(16:0/16:1n7)
  • PC(16:0/16:1w7)
  • PC(32:1)
  • Phosphatidyl-L-serine
  • phosphatidyl-L-serines
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(16:0/16:1)
  • Phosphatidylcholine(16:0/16:1n7)
  • Phosphatidylcholine(16:0/16:1w7)
  • Phosphatidylcholine(32:1)
  • (2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphate
  • (2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphate
  • (R-(Z))-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxo-9-hexadecenyl)oxy)-3,5,9-trioxa-4-phosphapentacosan-1-aminium, hydroxide, inner salt, 4-oxide
  • 1-C16:0-2-C16:1(Omega-7)-phosphatidylcholine
  • 1-Hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphocholine
  • 1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
  • 1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine zwitterion
  • 1-Palmitoyl-2-palmitoleoyl-GPC
  • 1-Palmitoyl-2-palmitoleoyl-GPC (16:0/16:1)
  • GPC(16:0/16:1)
  • PC(16:0/16:1omega7)
  • Phosphatidylcholine(16:0/16:1omega7)
  • sn-1-Palmitoyl-2-palmitoleoylphosphatidylcholine
  • (2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphoric acid
  • (2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acid
  • Palmitoylpalmitoleoylphosphatidylcholine
  • 1-(16,16,16-Trideuteriopalmitoyl)-2-palmitoleoyl-sn-glycero-3-phosphocholine
  • 1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine, (Z)-isomer
  • (CD3-16.0)(16.1)PC
  • PPA-GPC
  • 1-Palmitoyl-2-palmitoleoyl-sn-glycero-phosphatidylcholine
  • 1-Palmitoyl-2-palmitoleoylphosphatidylcholine
  • GPC(16:0/16:1(9Z))
  • GPC(16:0/16:1n7)
  • GPC(16:0/16:1W7)
  • GPC(32:1)
  • GPCho(16:0/16:1(9Z))
  • L-alpha-1-Palmitoyl-2-palmitoleoylphosphatidylcholine
  • L-Α-1-palmitoyl-2-palmitoleoylphosphatidylcholine
  • Phosphatidylcholine(16:0/16:1(9Z))
  • PC(16:0/16:1(9Z))
CAS number8002-43-5
WeightAverage: 732.023
Monoisotopic: 731.546504989
InChI KeyQIBZFHLFHCIUOT-NPBIGWJUSA-N
InChIInChI=1S/C40H78NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h17,19,38H,6-16,18,20-37H2,1-5H3/b19-17-/t38-/m1/s1
IUPAC Name(2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC40H78NO8P
SMILESCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility2.7e-05 g/LALOGPS
logP5.25ALOGPS
logP7.75ChemAxon
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 Count39ChemAxon
Refractivity216.98 m³·mol⁻¹ChemAxon
Polarizability89.46 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 Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(16:0/16:1(9Z))PW002874 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arachidonic acid metabolismec00590 Map00590
Glycerophospholipid metabolismec00564 Map00564
Linoleic acid metabolismec00591 Map00591
alpha-Linolenic acid metabolismec00592 Map00592
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
922500 ± 77375 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
2095750 ± 13675 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-1d66d0ec956bdface71cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-44d5972c060b53c05b48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900411200-ae8dad5c281477ff153cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-72e4b10a8d04de492e21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000001900-6d29a9c4f6d92278bb69JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0500391100-08250c65eb49ae519c73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-27ef027a037d0c8fadfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-d35161e016d19536fc33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-15mi-0090000400-a59199772bc703052242JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-692892d313dcd3995c61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000001900-d2164a22b9f090f20896JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-0100691100-63d302399382651c1621JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-6ea32ad4dc08edccb04bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-909418a92ec1ce82912bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900411200-b64debf7414aabba33f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-8dbe5f937df1e45f5cecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090022700-807b34d8325f37b8f816JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1091100000-64990f74ac4df09a68d4JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18303
HMDB IDHMDB07969
Pubchem Compound ID6323481
Kegg IDC00157
ChemSpider ID4947751
FOODB IDNot Available
WikipediaLecithin
BioCyc IDPHOSPHATIDYLCHOLINE