PC(18:0/14:1(9Z)) (YMDB01888)

Identification
YMDB IDYMDB01888
NamePC(18:0/14:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:0/14:1(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(18:0/14:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, 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
  • GPCho(18:0/14:1)
  • GPCho(18:0/14:1n5)
  • GPCho(18:0/14:1w5)
  • GPCho(32:1)
  • Lecithin
  • PC(18:0/14:1)
  • PC(18:0/14:1n5)
  • PC(18:0/14:1w5)
  • PC(32:1)
  • Phosphatidylcholine(18:0/14:1)
  • Phosphatidylcholine(18:0/14:1n5)
  • Phosphatidylcholine(18:0/14:1w5)
  • Phosphatidylcholine(32:1)
  • 1-stearoyl-2-myristoleoyl-sn-glycero-3-phosphocholine
  • PC(18:0/14:1)
  • Phosphatidylcholine(18:0/14:1)
  • Lecithin
  • GPCho(32:1)
  • Phosphatidylcholine(32:1)
  • GPCho(18:0/14:1)
  • PC(32:1)
  • 1-Octadecanoyl-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphocholine
  • PC(18:0/14:1(9Z))
CAS numberNot Available
WeightAverage: 732.023
Monoisotopic: 731.546504989
InChI KeyDHRQNMSQBJKUCK-KXQOOQHDSA-N
InChIInChI=1S/C40H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-22-17-15-13-11-9-7-2/h13,15,38H,6-12,14,16-37H2,1-5H3/t38-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-3-(octadecanoyloxy)-2-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Namelecithin
Chemical FormulaC40H78NO8P
SMILESCCCCCCCCCCCCCCCCCC(=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 Solubility2.3e-05 g/LALOGPS
logP5.27ALOGPS
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
Polarizability89.38 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
0.098 ± 0.0049 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, Positivesplash10-053i-8190141300-575a2c492a5a1f457c94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06a0-4391020100-5ed024a4f2a68fa9d9a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9173022000-9467c8315b7e66958cfbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000200-f385a08fc46cb9201b89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0090001000-8e5da632c8d2e7f0cf0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05rr-3190000000-03cc0330d9bc21cf77a6JSpectraViewer
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, Positivesplash10-0089-1900231200-7018d1537e5bacd73a39JSpectraViewer
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-0600491100-de4f0908861ded398a7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-8dbe5f937df1e45f5cecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090032800-6d80e456e31bb59dc3bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1091000000-8d2fcfb008730ed9549eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-27ef027a037d0c8fadfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000900-3c46c0bb6a484038d204JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0090000400-4a5540152a5b740f4a4dJSpectraViewer
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, Positivesplash10-0pc0-0101491100-1c6cebcfdf25c755c9dcJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89667
HMDB IDHMDB08032
Pubchem Compound ID52922643
Kegg IDC00157
ChemSpider ID24766700
FOODB IDFDB025223
Wikipedia IDNot Available
BioCyc IDNot Available