Record Information
Version1.0
Creation date2011-09-21 01:03:33 UTC
Update date2015-07-21 06:58:35 UTC
Primary IDFDB025924
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:0)
DescriptionPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:0) 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:0), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of arachidic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the arachidic acid moiety is derived from peanut oil. 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Docosahexaenoyl-2-arachidonyl-sn-glycero-3-ocholineHMDB
1-docosahexaenoyl-2-arachidonyl-sn-glycero-3-phosphocholinehmdb
Atidylcholine(22:6/20:0)HMDB
Atidylcholine(22:6N3/20:0)HMDB
Atidylcholine(22:6W3/20:0)HMDB
GPCho(22:6/20:0)hmdb
GPCho(22:6n3/20:0)hmdb
GPCho(22:6w3/20:0)hmdb
PC(22:6/20:0)hmdb
PC(22:6n3/20:0)hmdb
PC(22:6w3/20:0)hmdb
Phosphatidylcholine(22:6/20:0)hmdb
Phosphatidylcholine(22:6n3/20:0)hmdb
Phosphatidylcholine(22:6w3/20:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP6.55ALOGPS
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
Polarizability103.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC50H88NO8P
IUPAC name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C50H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25,27,30,32,36,38,48H,6-7,9,11-13,15,17-19,21,23-24,26,28-29,31,33-35,37,39-47H2,1-5H3/t48-/m1/s1
InChI KeyBINZSSJRRWYPEG-QSCHNALKSA-N
Isomeric SMILES[H][C@@](COC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC
Average Molecular Weight862.2094
Monoisotopic Molecular Weight861.624755309
Classification
DescriptionThis compound 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
  • Dialkyl phosphate
  • Fatty acid ester
  • Choline
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
SpectraNot Available
ChemSpider ID24767395
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound ID52923707
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB08734
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 IDLecithin
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
Enzymes
NameGene NameUniProt ID
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Phospholipase D2PLD2O14939
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Choline kinase alphaCHKAP35790
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Phospholipase D6PLD6Q8N2A8
Lecithin retinol acyltransferaseLRATO95237
Phosphatidylserine synthase 1PTDSS1P48651
Eosinophil lysophospholipaseCLCQ05315
Neuropathy target esterasePNPLA6Q8IY17
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
Phosphatidylethanolamine-binding protein 1PEBP1P30086
Phosphatidylethanolamine-binding protein 4PEBP4Q96S96
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference