Showing metabocard for PC(16:0/20:4(5Z,8Z,11Z,14Z)) (LMDB00491)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:02 UTC
Update Date2016-07-20 21:01:36 UTC
LmdbLMDB00491
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(16:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(16:0/20:4(5Z,8Z,11Z,14Z)) 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(16:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the arachidonic acid moiety is derived from animal fats and eggs. 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
ValueSource
1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z-icosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-O-Hexadecanoyl-2-O-arachidonoyl-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-arachidonoyl-GPCChEBI
1-Palmitoyl-2-arachidonoyl-GPC (16:0/20:4)ChEBI
1-Palmitoyl-2-arachidonyl-GPCChEBI
1-Palmitoyl-2-arachidonyl-phosphatidylcholineChEBI
GPC(16:0/20:4)ChEBI
GPCho(16:0/20:4)ChEBI
GPCho(16:0/20:4omega6)ChEBI
GPCho(16:0/5Z,8Z,11Z,14Z-20:4)ChEBI
GPCho(36:4)ChEBI
LecithinChEBI
PAPCChEBI
PC(16:0/20:4)ChEBI
PC(16:0/20:4omega6)ChEBI
PC(36:4)ChEBI
PC[16:0/20:4(5Z,8Z,11Z,14Z)]ChEBI
Phosphatidylcholine(16:0/20:4)ChEBI
Phosphatidylcholine(16:0/20:4omega6)ChEBI
Phosphatidylcholine(16:0/20:4W6)ChEBI
Phosphatidylcholine(36:4)ChEBI
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholineLipid Annotator, ChEBI, HMDB
PC(16:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
gpcho(16:0/20:4n6)HMDB
gpcho(16:0/20:4W6)HMDB
PC Aa C36:4HMDB
PC(16:0/20:4n6)HMDB
PC(16:0/20:4W6)HMDB
Phosphatidylcholine(16:0/20:4n6)HMDB
(1-Palmitoyl-2-arachidonoyl)-3-lecithinHMDB
1-Palmitoyl-2-arachidononyllecithinHMDB
1-Palmitoyl-2-arachidonoyl-3-phosphatidylcholineHMDB
1-Palmitoyl-2-arachidonoyl-3-sn-phosphatidylcholineHMDB
1-Palmitoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-2-arachidonoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-arachidonoylphosphatidylcholineHMDB
1-Palmitoyl-2-arachidonyl phosphatidylcholineHMDB
1-Palmitoyl-2-arachidoyllecithinHMDB
GPC(16:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPC(16:0/20:4n6)HMDB
GPC(16:0/20:4w6)HMDB
GPC(36:4)HMDB
GPCho(16:0/20:4(5Z,8Z,11Z,14Z))HMDB
OxPAPCHMDB
PalmitoylarachidonoylphosphatidylcholineHMDB
Phosphatidylcholine(16:0/20:4(5Z,8Z,11Z,14Z))HMDB
Chemical FormulaC44H80NO8P
Average Molecular Weight782.0817
Monoisotopic Molecular Weight781.562155053
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h14,16,20-21,23,25,29,31,42H,6-13,15,17-19,22,24,26-28,30,32-41H2,1-5H3/b16-14-,21-20-,25-23-,31-29-/t42-/m1/s1
InChI KeyIIZPXYDJLKNOIY-JXPKJXOSSA-N
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.75ALOGPS
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
Polarizability94.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-95a10c93ea7d71892a44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-da1f205f6fe8475ad9edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900230300-e67f19562f8287141f74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-3c72155bce4155773a03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-064c081755895a2e4178Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0900369110-641798d8c49b142e6431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-08d6fcb41388b1c681f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000090-90efb7f318dd780383adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-15mi-0099000090-27919d996c24759a1958Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2534b1e8e0eb889fbec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0053030900-8c6e4a90c9a9ffdae7e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5392100000-8318782705fdc1fd364eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-bc2a7ab6e102186d0c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-1f8c8c5ddd6d8082b38dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-0200669400-9e3134e6eb0b42a5d878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-440a71e9c384cc6f77ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-9035a7e163ecdf01e45fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-70c8bbde35e591b59ac9Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0007982
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8923140
ChEBI ID73003
PubChem Compound ID10747814
Kegg Compound IDNot Available
YMDB IDYMDB01853
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available