Showing metabocard for PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (LMDB00510)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:28 UTC
Update Date2016-07-19 23:32:11 UTC
LmdbLMDB00510
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPC(20:0/22:6(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(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The arachidic acid moiety is derived from peanut 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidonyl-2-docosahexaenoyl-sn-glycero-3-phosphocholineChEBI
GPCho(20:0/22:6n3)ChEBI
GPCho(20:0/22:6W3)ChEBI
PC(20:0/22:6n3)ChEBI
PC(20:0/22:6W3)ChEBI
Phosphatidylcholine(20:0/22:6n3)ChEBI
Phosphatidylcholine(20:0/22:6W3)ChEBI
Phosphatidylcholine(42:6)Lipid Annotator, HMDB
Phosphatidylcholine(20:0/22:6)Lipid Annotator, HMDB
GPCho(42:6)Lipid Annotator, HMDB
PC(42:6)Lipid Annotator, HMDB
PC(20:0/22:6)Lipid Annotator, HMDB
PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
LecithinLipid Annotator, HMDB
1-eicosanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(20:0/22:6)Lipid Annotator, HMDB
Chemical FormulaC50H88NO8P
Average Molecular Weight862.2094
Monoisotopic Molecular Weight861.624755309
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)OC[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/C50H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25,27,31,33,37,39,48H,6-7,9,11-13,15,17-19,21,23-24,26,28-30,32,34-36,38,40-47H2,1-5H3/b10-8-,16-14-,22-20-,27-25-,33-31-,39-37-/t48-/m1/s1
InChI KeyWAFWSBFKIPCFOF-ZDAJSWCOSA-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 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
logP6.54ALOGPS
logP10.39ChemAxon
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 Count44ChemAxon
Refractivity268.57 m³·mol⁻¹ChemAxon
Polarizability103.57 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, Positivesplash10-01q0-9055041130-34f149439dc84bfc1c0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03em-5295021010-23c183d826df079026fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fs9-9087002000-f3d4c553bd98c80d9ecdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000040-f29b2a428e9a97e83cc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0059000100-13870a67f6b8d0498c1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vl-6069100000-ce15f248d2c9f3b70c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-da4c76a3b203100f7b13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0006003090-21621c543afbb1f4bf56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3049000000-eed404d803c9eafc1540Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-3741652d888dcadea0ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-0cbd6b63b1d3753374d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-0200498040-eb18dfa8790f43d4ec20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-0ad943077e2468177956Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-0861374ebbd366c5fa86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0900170930-4b1086474fc743fc1357Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-7e3be7329e045e5fd946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0003000090-0a54df7a8f13057ed3ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03i2-0009000040-498cc2372caccd915c2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-c5ab242da8d8eff69efaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-66ae9033a1e31e803fceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041030-030e970fb10e5eb20266Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.34 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.37 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.36 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.4 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0008288
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 ID24766949
ChEBI ID86221
PubChem Compound ID24779053
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available