Record Information
Version1.0
Creation date2015-05-07 18:54:06 UTC
Update date2020-09-17 15:37:09 UTC
Primary IDFDB030253
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-palmitoyl-2-linoleoyl-phosphatidylcholine
DescriptionPC(16:0/18:2(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(16:0/18:2(9Z,12Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl to the C-2 atom. 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. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
CAS Number6931-84-6
Structure
Thumb
Synonyms
SynonymSource
1-Palmitoyl-2-linoleoyl-GPCChEBI
1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2)ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholineChEBI
1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholineChEBI
1-Palmitoyl-2-linoleoylphosphatidylcholineChEBI
GPC(16:0/18:2)ChEBI
GPCho 16:0/18:2(9Z,12Z)ChEBI
GPCho(16:0/18:2(9Z,12Z))ChEBI
GPCho(16:0/18:2)ChEBI
GPCho(16:0/18:2omega6)ChEBI
LecithinChEBI
PC 16:0/18:2(9Z,12Z)ChEBI
PC(16:0/18:2)ChEBI
PC(16:0/18:2omega6)ChEBI
PC(34:2)ChEBI
Phosphatidylcholine 16:0/18:2(9Z,12Z)ChEBI
Phosphatidylcholine(16:0/18:2(9Z,12Z))ChEBI
Phosphatidylcholine(16:0/18:2)ChEBI
Phosphatidylcholine(16:0/18:2omega6)ChEBI
Gpcho(34:2)HMDB
Phosphatidylcholine(34:2)HMDB
2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholineHMDB
Palmitoyl-linoleoatephosphatidylcholineHMDB
PLPCHMDB
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-linoleoyl-3-phosphatidylcholineHMDB
1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholineHMDB
1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholineHMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholineHMDB
1-Palmitoyl-2-linoleoyllecithinHMDB
GPC(16:0/18:2(9Z,12Z))HMDB
GPC(16:0/18:2n6)HMDB
GPC(16:0/18:2W6)HMDB
GPC(34:2)HMDB
GPCho(16:0/18:2n6)HMDB
GPCho(16:0/18:2W6)HMDB
L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholineHMDB
L-Α-1-palmitoyl-2-linoleoylphosphatidylcholineHMDB
PC(16:0/18:2n6)HMDB
PC(16:0/18:2W6)HMDB
Phosphatidylcholine(16:0/18:2n6)HMDB
Phosphatidylcholine(16:0/18:2W6)HMDB
PC(16:0/18:2(9Z,12Z))Lipid Annotator, ChEBI
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
Polarizability92.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H80NO8P
IUPAC name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1
InChI KeyJLPULHDHAOZNQI-ZTIMHPMXSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
Average Molecular Weight758.0603
Monoisotopic Molecular Weight757.562155053
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:

Health 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
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-b7304b809294dbb2ea74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0006-0000000940-6acae25b185d1a864052JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-537e946aca08f069e72bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-002f-0090000700-ecca901df00a9bff124cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-004i-0090000200-fa34aef5028ed4787c4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-004i-0090000000-d9440bc0e6a9f6cdaf65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-004i-0090000000-a5231d807bde53ae849aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, negativesplash10-056r-0090000000-23038428933dc1fcc66dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-056r-0090000000-ccce70356f7c7b18cbbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-056r-1090000000-32df8fc00b6e170aa02aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-004i-7190000000-811ed3f1fe9d51baf806JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 193V, negativesplash10-004i-9000000000-4bd8d3812cfdbafe42c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-aed1ee56f1886685cef5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-f70fecaaa4c193d6952dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-40ddf52a50eed646c5c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-79413b6bfab2c2699ebbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, negativesplash10-0006-0020000900-30d6507c6252bceda2abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, negativesplash10-002f-0090000800-e35e5d8e6ef65358f1d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-004i-0090000200-d82c61ca09093ce2f75aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, negativesplash10-004i-0090000000-a788f61f6153073cc513JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, negativesplash10-056r-0090000000-5242b45696e3aa936e70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 89V, negativesplash10-056r-0090000000-23038428933dc1fcc66dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-73b8731f1bdde398585fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-37c5a628d36a084e1386JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900231200-522c9f77a95c208b08bcJSpectraViewer
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