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PC(14:0/16:0) (YMDB01176)

Identification
YMDB IDYMDB01176
NamePC(14:0/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(14:0/16:0) 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(14:0/16:0), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one hexadecanoyl 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-myristoyl-2-palmitoyl-sn-glycero-3-phosphocholine
  • 1,2-Diacyl-sn-glycero-3-phosphocholine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-Phosphatidylcholine
  • Choline phosphatide
  • GPCho(14:0/16:0)
  • GPCho(30:0)
  • Lecithin
  • Lecithins
  • O3-Phosphatidyl-L-serine
  • PC(14:0/16:0)
  • PC(30:0)
  • Phosphatidyl-L-serine
  • phosphatidyl-L-serines
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(14:0/16:0)
  • Phosphatidylcholine(30:0)
  • 1-Myristoyl-2-palmitoyl-GPC
  • 1-Myristoyl-2-palmitoyl-GPC (14:0/16:0)
  • 1-Myristoyl-2-palmitoylphosphatidylcholine
  • 1-Tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine
  • 1-Tetradecanoyl-2-hexadecanoylphosphatidylcholine
  • GPC(14:0/16:0)
  • MPPC
CAS number8002-43-5
WeightAverage: 705.9857
Monoisotopic: 705.530854925
InChI KeyRFVFQQWKPSOBED-PSXMRANNSA-N
InChIInChI=1S/C38H76NO8P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39(3,4)5)34-44-37(40)30-28-26-24-22-20-17-15-13-11-9-7-2/h36H,6-35H2,1-5H3/t36-/m1/s1
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC38H76NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
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 Solubility3.4e-05 g/LALOGPS
logP4.95ALOGPS
logP7.22ChemAxon
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
Refractivity206.66 m³·mol⁻¹ChemAxon
Polarizability87.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cell envelope
  • Golgi
  • mitochondrion
  • endoplasmic reticulum
  • vacuole
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(14:0/16:0)PW002859 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 Reactions
PC(14:0/16:0) → PE(14:0/16:1(9Z)) + Carbon dioxide
L-Serine + CDP-diacylglycerol ↔ Cytidine monophosphate + PC(14:0/16:0) + hydron
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
19000 ± 11775 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
85250 ± 8425 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, Positivesplash10-0002-0000915000-bc584558990797312c6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pdi-0090000200-2c15a5a90b5c77a43bb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0190001000-380e9a694bb22e2c54a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4190000000-e4fece5b9cba2951ca1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-7615039fbfae408d95f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000001900-984ab4028567ba2b66bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0101791100-97808bd3a382a5e63f97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-c6fb3bc05eaaa84c86e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zi0-0090012500-75c25faf094705411d6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2191000000-fe6c58e1684ed4b19b23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-b00a0ca4532ff9182094JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000001900-4bbfc80efe35c8e1c7e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0600491100-d3be2cced1b82ac1c455JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-ce96887ed69b9e85f7a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-fe4e7280392995d009f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900412100-713da14b61754e31d304JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-4857d5d4f8976860ccc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-80adb7a66fc0aee6315eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0090000400-5f272dc8d69ac17f55ecJSpectraViewer
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 IDHMDB07869
Pubchem Compound ID6323481
Kegg IDC00157
ChemSpider ID114798
FOODB IDFDB025061
WikipediaLecithin
BioCyc IDPHOSPHATIDYLCHOLINE