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Record Information
Version1.0
Creation Date2016-07-13 19:53:25 UTC
Update Date2021-04-30 20:57:45 UTC
LmdbLMDB00599
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPC(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of Stearyl alcohol at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The Stearyl alcohol moiety is derived from beef fat, fish oil, while the docosahexaenoic acid moiety is derived from fish oils. 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
Synonyms
ValueSource
1-Stearyl-2-docosahexaenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(18:0/22:6)HMDB
Gpcho(18:0/22:6n3)HMDB
Gpcho(18:0/22:6W3)HMDB
Gpcho(40:6)HMDB
LecithinHMDB
PC Ae C40:6HMDB
PC(18:0/22:6)HMDB
PC(18:0/22:6n3)HMDB
PC(18:0/22:6W3)HMDB
PC(40:6)HMDB
PC(O-40:6)HMDB
Phosphatidylcholine(18:0/22:6)HMDB
Phosphatidylcholine(18:0/22:6n3)HMDB
Phosphatidylcholine(18:0/22:6W3)HMDB
Phosphatidylcholine(40:6)HMDB
1-Octadecanyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC48H86NO7P
Average Molecular Weight820.1727
Monoisotopic Molecular Weight819.614190623
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C48H86NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-48(50)56-47(46-55-57(51,52)54-44-42-49(3,4)5)45-53-43-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25-26,29,31,35,37,47H,6-7,9,11-13,15,17-19,21,23-24,27-28,30,32-34,36,38-46H2,1-5H3/b10-8-,16-14-,22-20-,26-25-,31-29-,37-35-/t47-/m1/s1
InChI KeyQBZALASVZLFAHF-KYPHJRDXSA-N
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
Ontology
StatusDetected and 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
logP6.64ALOGPS
logP9.88ChemAxon
logS-7.4ALOGPS
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 Count42ChemAxon
Refractivity259.62 m³·mol⁻¹ChemAxon
Polarizability99.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9125212130-1a88fcd34e00a314650eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2i-6398112210-89ac61f45de5b59cce7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gz0-9067002100-3a7da28c0ea8988a187cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0027000390-cfec9a5183e21fb2575aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2076200920-65dbb86c092ce1056b09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7079200000-3bd694666ab472a7dd3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-1ef5199e0232e322e510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000000090-1ef5199e0232e322e510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004o-0007300920-1ace0a5e883fd36e3bf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-2cd3025cf49877e0af78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0003002390-ba70665a9c2682aac1e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4289200000-6fc0f40ec8c0c4fa9e48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000090-5335bab2e85ba5d5b2d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000090-5335bab2e85ba5d5b2d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900141160-345741e30251bd4d4c07Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified1.12 +/- 0.56 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified1.869 +/- 0.3864 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.6623 +/- 0.7479 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.9334 +/- 0.5624 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.9065 +/- 0.6909 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.4469 +/- 0.424 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.8836 +/- 0.5503 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified2.0895 +/- 1.1539 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.6185 +/- 0.5455 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected and Quantified1.7735 +/- 0.8673 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.8716 +/- 0.6202 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified1.7321 +/- 0.4637 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified2.5 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified2.6 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified1.5 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified2.3 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified1.7779 +/- 0.5059 uM
Normal
Ovine
    • Goldansaz et al.,...
details
DrugBank IDNot Available
HMDB IDHMDB0013422
FooDB IDFDB029422
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24822905
ChEBI ID86252
PubChem Compound ID24779341
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available