Showing Metabocard for 1-tetradecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine (BASm0007489)

Common Name1-tetradecanoyl-2-(5z,8z,11z,14z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
DescriptionPC(14:0/20:4(5Z,8Z,11Z,14Z)) 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(14:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidonic acid moiety is derived from animal fats and eggs. 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 FormulaC42H76NO8P
Average Mass754.02850
Monoisotopic Mass753.53085
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2r)-2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h14,16,19-20,22-23,27,29,40H,6-13,15,17-18,21,24-26,28,30-39H2,1-5H3/b16-14-,20-19-,23-22-,29-27-/t40-/m1/s1
InChI KeySRQSAJRUMDQMMS-NLDJLLEISA-N
CHEBI IDCHEBI:86102
HMDB IDHMDB0007883
Pathways
NameSMPDB/PathBank
Arachidonic Acid Metabolism
Piroxicam Action Pathway
Acetylsalicylic Acid Action Pathway
Etodolac Action Pathway
Ketoprofen Action Pathway
Ibuprofen Action Pathway
Rofecoxib Action Pathway
Diclofenac Action Pathway
Sulindac Action Pathway
Celecoxib Action Pathway
Ketorolac Action Pathway
Suprofen Action Pathway
Bromfenac Action Pathway
Indomethacin Action Pathway
Meloxicam Action Pathway
Mefenamic Acid Action Pathway
Oxaprozin Action Pathway
Nabumetone Action Pathway
Valdecoxib Action Pathway
Naproxen Action Pathway
Diflunisal Action Pathway
Leukotriene C4 Synthesis Deficiency
Antipyrine Action Pathway
Antrafenine Action Pathway
Carprofen Action Pathway
Etoricoxib Action Pathway
Fenoprofen Action Pathway
Flurbiprofen Action Pathway
Magnesium salicylate Action Pathway
Lumiracoxib Action Pathway
Lornoxicam Action Pathway
Phenylbutazone Action Pathway
Nepafenac Action Pathway
Trisalicylate-choline Action Pathway
Tolmetin Action Pathway
Tiaprofenic Acid Action Pathway
Tenoxicam Action Pathway
Salsalate Action Pathway
Salicylate-sodium Action Pathway
Salicylic Acid Action Pathway
Acetaminophen Action Pathway
Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))
Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))
StateNot Available
Water Solubility3.18e-05 g/l
logP5.36
logS-7.40
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
Refractivity229.53 m³·mol⁻¹
Polarizability89.94

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