Common Name1-tetradecanoyl-2-(4z,7z,10z,13z,16z,19z-docosahexaenoyl)-sn-glycero-3-phosphocholine
DescriptionPC(14:0/22:6(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(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, 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
Molecular FormulaC44H76NO8P
Average Mass778.04990
Monoisotopic Mass777.53085
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(tetradecanoyloxy)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-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILESCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C44H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h8,10,14,16,19-20,22-23,25,27,31,33,42H,6-7,9,11-13,15,17-18,21,24,26,28-30,32,34-41H2,1-5H3/b10-8-,16-14-,20-19-,23-22-,27-25-,33-31-/t42-/m1/s1
InChI KeyHAIPHKFLSXSDAN-BLOCXYQCSA-N
CHEBI IDCHEBI:86162
HMDB IDHMDB0007892
Pathways
NameSMPDB/PathBank
Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
StateNot Available
Water Solubility3.27e-05 g/l
logP5.48
logS-7.41
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)-6.75
Hydrogen Acceptor Count4
Hydrogen Donor Count0
Polar Surface Area111.19 Ų
Rotatable Bond Count38
Physiological Charge0
Formal Charge0
Refractivity240.97 m³·mol⁻¹
Polarizability90.71

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