PC(18:2(9Z,12Z)/16:0) (YMDB01956)

Identification
YMDB IDYMDB01956
NamePC(18:2(9Z,12Z)/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:2(9Z,12Z)/16:0) 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(18:2(9Z,12Z)/16:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal 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-linoleoyl-2-palmitoyl-sn-glycero-3-phosphocholine
  • GPCho(18:2/16:0)
  • GPCho(18:2n6/16:0)
  • GPCho(18:2w6/16:0)
  • GPCho(34:2)
  • Lecithin
  • PC(18:2/16:0)
  • PC(18:2n6/16:0)
  • PC(18:2w6/16:0)
  • Phosphatidylcholine(18:2/16:0)
  • Phosphatidylcholine(18:2n6/16:0)
  • Phosphatidylcholine(18:2w6/16:0)
  • Phosphatidylcholine(34:2)
  • PC(34:2)
  • 1-Linoleoyl-2-palmitoyl-sn-glycero-3-phosphocholine
  • GPCho(18:2/16:0)
  • GPCho(18:2n6/16:0)
  • GPCho(18:2W6/16:0)
  • PC(18:2/16:0)
  • PC(18:2n6/16:0)
  • PC(18:2W6/16:0)
  • Phosphatidylcholine(18:2/16:0)
  • Phosphatidylcholine(18:2n6/16:0)
  • Phosphatidylcholine(18:2W6/16:0)
  • Phosphatidylcholine(34:2)
  • Lecithin
  • GPCho(34:2)
  • 1-(9Z,12Z-Octadecadienoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine
  • PC(18:2(9Z,12Z)/16:0)
CAS numberNot Available
WeightAverage: 758.0603
Monoisotopic: 757.562155053
InChI KeyFWMYJLDHIVCJCT-RRHRGVEJSA-N
InChIInChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/t40-/m1/s1
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namelecithin
Chemical FormulaC42H80NO8P
SMILESCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=CCC=CCCCCC)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 Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.5e-05 g/LALOGPS
logP5.48ALOGPS
logP8.28ChemAxon
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 Count40ChemAxon
Refractivity227.3 m³·mol⁻¹ChemAxon
Polarizability91.5 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
3 ± 0 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-7190141300-64cf16a1f4bb580de806JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-3291010000-9c22e5fea4ca875206f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8293020000-f7b9ba3789873897aa07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bvi-0090000200-c4fe261c38786e7f405fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0090001000-eedb85e1cd28f483fb2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vr-3090000000-aae5334ae894311fada5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-e3f5d1861df776418aefJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-c4175ed37e12d6b3fe7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0090000400-3aa458c3b4d84b3cc9dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-8ecd56b42b9f6b271e5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-ab98c2d6a7f897263cd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0500190100-b9358d0778fd0366a3fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-b382b9772ae071121f32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-e509931f6dd2f1ba96fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-63cdc518605ec44f8344JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000900-4f45d46462d3badb869eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0091043800-39798c4181c15566b952JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-4190300000-1e3e90f4a5cd94bda6dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-02ab676d31620f046e54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-80f99b213a3cb752bf9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100390200-7fac6ad45632aa2a3cd9JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86099
HMDB IDHMDB08133
Pubchem Compound ID24778972
Kegg IDC00157
ChemSpider ID24766796
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available