PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (YMDB01985)

Identification
YMDB IDYMDB01985
NamePC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) 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(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)), in particular, consists of two chains of g-linolenic acid at the C-1 and C-2 positions. The g-linolenic acid moieties are derived from 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
  • 1,2-dig-linolenoyl-rac-glycero-3-phosphocholine
  • GPCho(18:3/18:3)
  • GPCho(18:3n6/18:3n6)
  • GPCho(18:3w6/18:3w6)
  • GPCho(36:6)
  • Lecithin
  • PC(18:3/18:3)
  • PC(18:3n6/18:3n6)
  • PC(36:6)
  • Phosphatidylcholine(18:3/18:3)
  • Phosphatidylcholine(18:3n6/18:3n6)
  • Phosphatidylcholine(18:3w6/18:3w6)
  • Phosphatidylcholine(36:6)
  • PC(18:3w6/18:3w6)
  • 1,2-Dig-linolenoyl-rac-glycero-3-phosphocholine
  • Phosphatidylcholine(36:6)
  • GPCho(18:3/18:3)
  • PC(18:3/18:3)
  • GPCho(36:6)
  • Phosphatidylcholine(18:3/18:3)
  • Lecithin
  • PC(36:6)
  • 1,2-Di(6Z,9Z,12Z-octadecatrienoyl)-rac-glycero-3-phosphocholine
  • PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))
  • 1,2-Digamma-linolenoyl-GPC
  • 1,2-Digamma-linolenoyl-sn-glycero-3-phosphocholine
  • 1,2-Digamma-linolenoyl-sn-glycero-phosphatidylcholine
  • 1,2-Dilinolenoyl-GPC
  • GPC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))
  • GPC(18:3/18:3)
  • GPC(18:3n6/18:3n6)
  • GPC(18:3w6/18:3w6)
  • GPC(36:6)
  • GPCho(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))
  • GPCho(18:3n6/18:3n6)
  • GPCho(18:3w6/18:3w6)
  • PC(18:3n6/18:3n6)
  • Phosphatidylcholine(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))
  • Phosphatidylcholine(18:3n6/18:3n6)
  • Phosphatidylcholine(18:3w6/18:3w6)
CAS numberNot Available
WeightAverage: 778.0499
Monoisotopic: 777.530854925
InChI KeyYNQXQNOLOMVDLG-HUESYALOSA-N
InChIInChI=1S/C44H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,26-29,42H,6-13,18-19,24-25,30-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2,3-bis[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H76NO8P
SMILESCCCCCC=CCC=CCC=CCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC=CCC=CCC=CCCCCC
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
logP5.39ALOGPS
logP7.72ChemAxon
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
Refractivity240.97 m³·mol⁻¹ChemAxon
Polarizability91.3 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
0.021 ± 0.00105 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, Positivesplash10-0gw0-9051062400-2ab5c3d7e57a46b9f0abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yr-6395053100-c11a9fac803d69a539aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9057042100-801279366073e36f1124JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000400-09785e8202c3360f75f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-8d2e3bfb83bae0d857e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090100000-b8f36391ccc83e0bd68eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-e97180150486da753e49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-cd910875d8659ad53678JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014k-0900139110-729a620391bf787edc7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e158c1e70dedba30b57eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-259bce635b325b3b4835JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900030300-f4f11a4f3ff53231bc3cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-41c33084af9f783c847dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-dd151cc7bd543b751825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0200249400-bc8c4d38f7130b86115dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-5a1f7e5d648203ccaa08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1091010400-143b161378be43e4d254JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4291000000-bc08a5584b3d5f3ac6d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-87e491c712a61c58fe72JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0010000090-a9763bdd0b25569e54adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03i0-0090000090-9c024dd2a2f08c7e97bcJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89557
HMDB IDHMDB08172
Pubchem Compound ID52922787
Kegg IDC00157
ChemSpider ID24766834
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available