Chemical Formula: C26H50NO7P

Chemical Formula C26H50NO7P

Found 55 metabolite its formula value is C26H50NO7P

2-linoleoyl-sn-glycero-3-phosphocholine

C26H50NO7P (519.332472)

1-linoleoyl-GPC (18:2)

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

C26H50NO7P (519.332472)

LysoPC(0:0/18:2(9Z,12Z))

(2-{[(2R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

C26H50NO7P (519.332472)

LysoPC(0:0/18:2(9Z,12Z)) is a lysophosphatidylcholine, which is a lysophospholipid. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2 as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(0:0/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-2 position.

LPC 18:2

1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine

C26H50NO7P (519.332472)

Annotation level-3

LPC(18:2)

1-Linoleoyl-glycero-3-phosphocholine

C26H50NO7P (519.332472)

1-Linoleoylglycerophosphocholine

2-[hydroxy-[2-hydroxy-3-[(9Z,12Z)-octadeca-9, 12-dienoyl]oxypropoxy]phosphoryl]oxyethyl-trimethylazanium

C26H50NO7P (519.332472)

PC(18:2/0:0)

3,5,9-Trioxa-4-phosphaheptacosa-11,13-dien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (R)-

C26H50NO7P (519.332472)

18:2 LYSO-PC

3,5,9-Trioxa-4-phosphaheptacosa-18,21-dien-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, [R-(Z,Z)]-

C26H50NO7P (519.332472)

Linoleoyllysolecithin

1-mono-, 3-(dihydrogen phosphate), monoester with choline hydroxide, inner salt

C26H50NO7P (519.332472)

1-linoleoyl-GPC (18:2)

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

C26H50NO7P (519.332472)

LysoPC(18:2(9Z,12Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-Rs are members of the G protein-coupled receptor family of integral membrane proteins. Lysopc(18:2(9z,12z)), also known as lysophosphatidylcholine(18:2/0:0) or lpc(18:2n6/0:0), is a member of the class of compounds known as 1-acyl-sn-glycero-3-phosphocholines. 1-acyl-sn-glycero-3-phosphocholines are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Thus, lysopc(18:2(9z,12z)) is considered to be a glycerophosphocholine lipid molecule. Lysopc(18:2(9z,12z)) is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Lysopc(18:2(9z,12z)) can be found in a number of food items such as japanese persimmon, jicama, rubus (blackberry, raspberry), and chinese bayberry, which makes lysopc(18:2(9z,12z)) a potential biomarker for the consumption of these food products. Lysopc(18:2(9z,12z)) can be found primarily in blood, feces, and urine, as well as throughout all human tissues. Moreover, lysopc(18:2(9z,12z)) is found to be associated with schizophrenia.