Record Information
Version1.0
Creation date2015-05-07 18:50:49 UTC
Update date2020-09-17 15:37:08 UTC
Primary IDFDB030223
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-18:2-2-18:2-sn-glycerol-3-phosphocholine
DescriptionPC(18:2(9Z,12Z)/18:2(9Z,12Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(18:2(9Z,12Z)/18:2(9Z,12Z)), in particular, consists of two 9Z,12Z-octadecadienoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
CAS Number998-06-1
Structure
Thumb
Synonyms
SynonymSource
(2R)-2,3-Bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl 2-(trimethylammonio)ethyl phosphateChEBI
(2R)-2,3-Bis{[(9Z,12Z)-octadeca-9,12-dienoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1,2-Di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1,2-Di-O-linoleoyl-sn-glycero-3-phosphocholineChEBI
1,2-Dilinoleoyl-sn-glycero-3-phosphocholineChEBI
DI-linoleoyl-3-sn-phosphatidylcholineChEBI
DilinoleoylphosphatidylcholineChEBI
DL-PCChEBI
DLNPCChEBI
DLPCChEBI
GPCho(18:2/18:2)ChEBI
GPCho(18:2n6/18:2n6)ChEBI
GPCho(18:2W6/18:2W6)ChEBI
L-DilinoleoyllecithinChEBI
PC(18:2/18:2)ChEBI
PC(18:2n6/18:2n6)ChEBI
PC(18:2W6/18:2W6)ChEBI
Phosphatidylcholine(18:2/18:2)ChEBI
Phosphatidylcholine(18:2n6/18:2n6)ChEBI
Phosphatidylcholine(18:2W6/18:2W6)ChEBI
(2R)-2,3-Bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
(2R)-2,3-Bis{[(9Z,12Z)-octadeca-9,12-dienoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1,2-Linoleoylphosphatidylcholine, 14C-labeled CPD, (R-(all Z))-isomerHMDB
1,2-Dilinoleoyl-3-glycerophosphocholineHMDB
1,2-LinoleoylphosphatidylcholineHMDB
DLPC LipidHMDB
DilinoleoyllecithinHMDB
Dilinoleoyl phosphatidylcholineHMDB
1,2-Linoleoyl-sn-glycero-3-phosphocholineHMDB
1,2-Linoleoylphosphatidylcholine, (R-(all Z))-isomerHMDB
Phosphatidylcholine(36:4)HMDB
LecithinHMDB
PC(36:4)HMDB
1,2-Dilinoleoyl-rac-glycero-3-phosphocholineHMDB
1,2-Di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phosphocholineHMDB
GPCho(36:4)HMDB
1,2-Dilinoleoyl-GPCHMDB
PC(18:2(9Z,12Z)/18:2(9Z,12Z))Lipid Annotator
Predicted Properties
PropertyValueSource
Water Solubility3.2e-05 g/LALOGPS
logP5.68ALOGPS
logP8.44ChemAxon
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 Count40ChemAxon
Refractivity238.74 m³·mol⁻¹ChemAxon
Polarizability93.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC44H80NO8P
IUPAC name(2-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C44H80NO8P/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/h14-17,20-23,42H,6-13,18-19,24-41H2,1-5H3/b16-14-,17-15-,22-20-,23-21-/t42-/m1/s1
InChI KeyFVXDQWZBHIXIEJ-LNDKUQBDSA-N
Isomeric SMILESCCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
Average Molecular Weight782.0817
Monoisotopic Molecular Weight781.562155053
Classification
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
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-001i-0000000900-bd3ed2ff47d70cb5ac3eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-001i-0400000900-d002062176d9e1a58fccSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-001i-0900000100-1d81bafed34be0680f8bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, positivesplash10-001i-0900000000-b42fac72a675be84234dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 65V, positivesplash10-001i-0900000000-a1756c5f56f420105ec6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-001i-0900000000-57ce459f0f2b4ef3b388Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 87V, positivesplash10-001i-1900000000-26d27e14f475fd58e101Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 98V, positivesplash10-001i-2900000000-ee4e32911559ac08e569Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-001i-3900000000-c96a527426c641063662Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 131V, positivesplash10-003i-7900000000-8fd87469bebc7841cfebSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 164V, positivesplash10-002s-9700000000-805c2bda88ecbe768134Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 196V, positivesplash10-002k-9500000000-739389c73c5b7af69f2bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 240V, positivesplash10-0002-9200000000-d6507de242e2b9f69119Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 286V, positivesplash10-0002-9000000000-747c2f7f10ab5dc686cbSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 351V, positivesplash10-0002-9000000000-e963880e5dd642c7c967Spectrum
MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0fe0-0000090600-6c4096785e931bdd859aSpectrum
MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0006-0000900000-d438f5570e710ae02ee6Spectrum
MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-08fr-0934000000-a2858d3a6aed2e863180Spectrum
MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0udi-0300090000-e353c4c82a0a4a7c7e36Spectrum
MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-000i-9200000000-b6ca8b900ee76df8ea58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-95a10c93ea7d71892a44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-da1f205f6fe8475ad9edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900030300-707d383caeedd787dae6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2534b1e8e0eb889fbec2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0080020900-5688f54205e1eea312abSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference