Common Name1-tetradecanoyl-2-(9z,12z-octadecadienoyl)-sn-glycero-3-phosphocholine
DescriptionPC(14:0/18:2(9Z,12Z)) 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(14:0/18:2(9Z,12Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the linoleic acid moiety is derived from seed 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 FormulaC40H76NO8P
Average Mass730.00710
Monoisotopic Mass729.53085
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional NameTrimethyl(2-{[(2r)-2-[(9z,12z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry Number92345-33-0
SMILESCCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h14,16,19-20,38H,6-13,15,17-18,21-37H2,1-5H3/b16-14-,20-19-/t38-/m1/s1
InChI KeyIWXJKHSPEQSQMD-GMGFYYQASA-N
CHEBI IDCHEBI:86094
HMDB IDHMDB0007874
Pathways
NameSMPDB/PathBank
Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))
Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))
StateNot Available
Water Solubility2.88e-05 g/l
logP5.13
logS-7.43
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)-6.74
Hydrogen Acceptor Count4
Hydrogen Donor Count0
Polar Surface Area111.19 Ų
Rotatable Bond Count38
Physiological Charge0
Formal Charge0
Refractivity218.10 m³·mol⁻¹
Polarizability88.29

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