PC(16:1(9Z)/14:1(9Z)) (YMDB01863)

Identification
YMDB IDYMDB01863
NamePC(16:1(9Z)/14:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:1(9Z)/14:1(9Z)) 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)/14:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the myristoleic acid moiety is derived from milk fats. 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-myristoleoyl-sn-glycero-3-phosphocholine
  • GPCho(16:1/14:1)
  • GPCho(16:1n7/14:1n5)
  • GPCho(16:1w7/14:1w5)
  • GPCho(30:2)
  • Lecithin
  • PC(16:1/14:1)
  • PC(16:1n7/14:1n5)
  • PC(16:1w7/14:1w5)
  • Phosphatidylcholine(16:1/14:1)
  • Phosphatidylcholine(16:1n7/14:1n5)
  • Phosphatidylcholine(16:1w7/14:1w5)
  • Phosphatidylcholine(30:2)
  • PC(30:2)
  • 1-Palmitoleoyl-2-myristoleoyl-sn-glycero-3-phosphocholine
  • GPCho(16:1n7/14:1n5)
  • GPCho(16:1W7/14:1W5)
  • PC(16:1n7/14:1n5)
  • PC(16:1W7/14:1W5)
  • Phosphatidylcholine(16:1n7/14:1n5)
  • Phosphatidylcholine(16:1W7/14:1W5)
  • Phosphatidylcholine(16:1/14:1)
  • Lecithin
  • GPCho(30:2)
  • PC(16:1/14:1)
  • Phosphatidylcholine(30:2)
  • GPCho(16:1/14:1)
  • 1-(9Z-Hexadecenoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholine
  • PC(16:1(9Z)/14:1(9Z))
CAS numberNot Available
WeightAverage: 701.9539
Monoisotopic: 701.499554797
InChI KeyWEVWHXAKLAWWAP-PSXMRANNSA-N
InChIInChI=1S/C38H72NO8P/c1-6-8-10-12-14-16-18-19-21-22-24-26-28-30-37(40)44-34-36(35-46-48(42,43)45-33-32-39(3,4)5)47-38(41)31-29-27-25-23-20-17-15-13-11-9-7-2/h13,15-16,18,36H,6-12,14,17,19-35H2,1-5H3/t36-/m1/s1
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC38H72NO8P
SMILESCCCCCCC=CCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCC
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
logP4.76ALOGPS
logP6.5ChemAxon
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 Count36ChemAxon
Refractivity208.9 m³·mol⁻¹ChemAxon
Polarizability83.96 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
0.018 ± 0.0009 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, Positivesplash10-000i-8190412200-69aefb2afb7f6cd3f73eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053i-4490111000-cddd9e51f52be7eab2c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9371041000-5c5fc3d4f150943129a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000200-0b0897bf9f4925390819JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0090000000-db0d065968bd886f3c90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdr-4190000000-6f9a8cf789b018427a21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-c0264bc5a3658a84089eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000001900-f99701a4c0dc029e939bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fis-0101791100-07091dabbadf7fa8ebb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-1fd7bbea2430b811e0ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-4b1c66063a5797985307JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900412100-d5b06fcc3b23dd902711JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-015b7563f35058194e4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-fd2ae918b9bd28bf4ae8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uii-0090000400-cd9d490ca073d32c9e59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-5e86fac3277edd257badJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000001900-d689ed047e4811394499JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-0700691100-b1b962c108a0c0b79340JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-c0783fc627a546653f44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090032800-dae7a83f9fa1abd8eda8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1191000000-b81065f019c21da75732JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86415
HMDB IDHMDB07999
Pubchem Compound ID52922434
Kegg IDC00157
ChemSpider ID24766668
FOODB IDFDB025190
Wikipedia IDNot Available
BioCyc IDNot Available