PC(O-16:0/18:2(9Z,12Z)) (YMDB02215)

Identification
YMDB IDYMDB02215
NamePC(O-16:0/18:2(9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(O-16:0/18:2(9Z,12Z)) is an ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Phosphatidylcholines are a class of phospholipids which incorporate choline as a headgroup. They are a major component of biological membranes and can be isolated from either egg yolk (in Greek lekithos) or soy beans from which they are mechanically extracted or chemically extracted using hexane. Phosphatidylcholines are such a major component of lecithin, that, in some contexts, the terms are sometime used as synonyms. However, lecithin extract consists of a mixture of phosphatidylcholine and other compounds. It is also used along with sodium taurocholate for simulating fed- and fasted-state biorelevant media in dissolution studies of highly-lipophilic drugs. Phosphatidylcholine is a major constituent of cell membranes, and also plays a role in membrane-mediated cell signalling. Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol. Some medical researchers are experimenting with using Phosphatidylcholine in a type of injection that will break down fat cells; to be used as an alternative to liposuction known as Injection lipolysis. (Wikipedia) 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
  • [(2R)-3-hexadecoxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-trimethylazaniumylethyl phosphate
  • 2-(9Z,12Z-Octadecadienoyl)-1-hexadecyl-sn-glycero-3-phosphocholine
  • 1-hexadecyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
  • PC(16:0e/18:2(9Z,12Z))
  • 2-(9Z,12Z-Octadecadienoyl)-1-hexadecyl-sn-glycero-3-phosphocholine
  • PC Ae C34:2
  • PC(O-34:2)
  • [(2R)-3-Hexadecoxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-trimethylazaniumylethyl phosphate
CAS number88542-95-4
WeightAverage: 744.0767
Monoisotopic: 743.582890495
InChI KeyIQACMFWAGALEAQ-VQJSHJPSSA-N
InChIInChI=1S/C42H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,41H,6-13,15,17-19,21,23-40H2,1-5H3/t41-/m1/s1
IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Chemical FormulaC42H82NO7P
SMILESCCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • 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 Solubility2.4e-05 g/LALOGPS
logP5.86ALOGPS
logP8.66ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity227.55 m³·mol⁻¹ChemAxon
Polarizability92.68 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
0.033 ± 0.00165 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, Positivesplash10-01q0-9170321300-dbd7856d52c0aa092c20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-3290111000-2345c437d6514d4c63c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-7090022000-2630e93789ae7b753477JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0090003700-619264aad469d6299fc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004u-1091006100-9abf3093eddcb9a13e76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-4091000000-70d3982de65c2c7f9291JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-23872d2e94db2d9fdf31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0060012900-27c3aa121cb366946f75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4091200000-64e10c7f3565c8d5c670JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-190e542fe7b67b8c2014JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000000900-190e542fe7b67b8c2014JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0061201900-3adf33f5c1cb71fb8333JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-414ec66860f431bd7276JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-414ec66860f431bd7276JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-1900341600-1c67b05fa14757dd6ff5JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB11151
Pubchem Compound ID6443157
Kegg IDNot Available
ChemSpider ID24822857
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available