Chemical Formula: C26H52NO7P
Chemical Formula C26H52NO7P
Found 78 metabolite its formula value is C26H52NO7P
LysoPC (18:1/0:0)
LysoPC(18:1(9Z)) 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(18:19Z)), in particular, consists of one chain of oleic acid at the C-1 position. The oleic acid moiety, an omega-9 fatty acid, is derived from various animal and vegetable sources such as olive oil, acai and grapeseed oil. 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. Lysophosphatidylcholines (LPC), also called lysolecithins, are a class of chemical compounds which are derived from phosphatidylcholines. They result from partial hydrolysis of phosphatidylcholines, which removes one of the fatty acid groups. The hydrolysis is generally the result of the enzymatic action of phospholipase A2. LPC is present as a minor phospholipid in the cell membrane (<=3\\%) and in the blood plasma (8-12\\%). Since LPCs are quickly metabolized by lysophosholypase and LPC-acyltransferase, they last only shortly in vivo. [Wikipedia]. Lysolecithin is found in many foods, some of which are cardamom, cucumber, common buckwheat, and rice.
LysoPC(18:1(11Z)/0:0)
LysoPC(18:1(11Z)) 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(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. 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. [HMDB] LysoPC(18:1(11Z)) 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(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. 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(0:0/18:1(9Z))
LysoPC(0:0/18:1(9Z)) 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(0:0/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-2 position.
LPC 18:1
Annotation level-3
Lyso-PC 18:1(9Z)
This mass spectral data is shown in Figure S7 of the publication.; Figure S7 shows that O attached precursor ions, [M+H+O*]+, are predominantly in the epoxide form. The [M+H+O*]+ ion is the product that [M+H]+ reacts with H2O microwave discharge (MSJ00187). The products of microwave discharge are mixture of gas-phase H*, OH*, and 3O (triplet O) radicals.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of HAD, and TOF analyzes the product ions.; MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). FRAGMENTATION_MODE is RID that is Radical Induced Dissociation; MALDI generates [M+H]+ ion, which is dissociated by the reaction with 3O (triplet O) generated by O2 microwave discharge.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of RID, and TOF analyzes the product ions.; This mass spectral data and fragment ions produced are shown in Figure S6_2 of the publication.; Relative intensity of the peaks m/z 180-199 is magnified by x5, those of the peaks m/z 200-507 by 100.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). MSJ00188 is shown in Figure 5 of the publication. The precursor ion is the [M+H+O]+ ion that is a major product ion of the reaction product of [M+H]+ with H2O microwave discharge (MSJ00187). In the present experiment, [M+H+O]+ ions are induced by the injection of 3O (triplet) from the microwave discharge of pure O2 gas.; Figure 5 shows that O attached precursor ions, [M+H+O]+, are predominantly in the epoxide form.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of HAD, and TOF analyzes the product ions.; MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). MALDI generates a stable [M+H]+ ion. [M+H]+ reacts with the mixture of OH* and H* radicals, and 3O (triplet O) atom that microwave discharge of H2O generates. The reaction products, consisting of [M+H+H*], [M+H+O]+ and [M+H+OH*]+ ions, are dissociated to give product ions, which are detected as RID product ions.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of RID, and TOF analyzes the product ions.; This mass spectral data is shown in Figure S5 of the publication. Fragment ions produced are explained in Scheme 2 of the publication. MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; Relative Intensity of the peaks is magnified; m/z 180-199 by x5, m/z 200-505 by x100; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). MALDI generates a stable [M+H]+ ion. Microwave discharge of H2O generates OH*, H* and 3O (triplet O) radicals. These radicals react with the stable [M+H]+ ion and give a mixture of [M+H+H*], [M+H+O]+ and [M+H+OH*]+ ions. In the present experiment, O2 gas is introduced after the H2O discharge.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of RID, and TOF analyzes the product ions.; This mass spectral data is shown in Figure 4(C) of the publication. Fragment ions produced are annotated in Scheme 2 of the publication. MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; Relative intensity of the peaks from m/z 300 to 499 is magnified by x10.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). RID is Radical Induced Dissociation; MALDI generates [M+H]+ ion, which is dissociated by the reaction with 3O (triplet O) generated by O2 microwave discharge.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of RID, and TOF analyzes the product ions.; This mass spectral data is shown in Figure 4(B) of the publication. Fragment ions produced are annotated in Scheme 2. MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; Relative Intensity of the peaks from m/z 300 to 499 is magnified by x10.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). What is Radical Induced Dissociation (RID)? Microwave discharge of H2O generates OH*, H* and 3O (triplet O) radicals. These radicals react to dissociate the stable [M+H]+ ion.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of RID, and TOF analyzes the product ions.; This mass spectral data is shown in Figure 4(A) of the publication. Fragment ions produced are annotated in Scheme 2. MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; Relative intensity of the peaks from m/z 300 to 499 is magnified by x100.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). This is an experiment to compare with MSJ00179 that uses Hydrogen Abstraction Dissociation (HAD) instead of CID for the dissociation of [M+H]+.; This mass spectral data is shown in Figure S3 of the publication.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of HAD, and TOF analyzes the product ions.; MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; The sample was injected by direct infusion.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). FRAGMENTATION_MODE is HAD that is Hydrogen Abstraction Dissociation; MALDI generates [M+H]+ ion, which is dissociated by the reaction with hydrogen radical (H*) generated by microwave-driven radical generator.; This mass spectral data is shown in Figure 1(A) of the publication.; The instrument consists of QIT-TOF where Q selects [M+H]+ ion, IT is an ion trap chamber for the reaction of HAD, and TOF analyzes the product ions.; MS data of the substance is MSJ00178; Figure 1(A) Inset in the publication.; The sample was injected by direct infusion.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL). This mass spectral data is shown in Figure 1(A) Inset of the publication.; The sample was injected by direct infusion of methanol solution.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.; The lipid standard was purchased from Avanti Polar Lipids (Alabaster, AL).
Platelet-activating factor
PC(P-16:0/2:0)
PC(18:1/0:0)
PC(18:1/0:0)[U]
PC(0:0/18:1)
Elaidin, 2-mono-,
PC(0:0/18:1)[U]
1-Elaidoyl-sn-glycero-3-phosphocholine
A lysophosphatidylcholine 18:1 in which the acyl group is at position 1 is elaidoyl [(9E)-octadec-9-enoyl] and the hydoxy group at position 2 is unsubstituted.
[2-hydroxy-3-[(E)-octadec-6-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
(2R)-2-(acetyloxy)-3-{[(9Z)-hexadec-9-en-1-yl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphate
[2-hydroxy-3-[(E)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[2-acetyloxy-3-[(Z)-hexadec-9-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2S)-3-hydroxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[3-[(Z)-16,16,17,17,18,18,18-heptadeuteriooctadec-9-enoyl]oxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] (Z)-henicos-11-enoate
[2-pentanoyloxy-3-[(Z)-tridec-9-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-tridec-9-enoxy]propan-2-yl] octanoate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-pentadec-9-enoxy]propan-2-yl] hexanoate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-octoxypropan-2-yl] (Z)-tridec-9-enoate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-heptadec-9-enoxy]propan-2-yl] butanoate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-nonadec-9-enoxy]propan-2-yl] acetate
[3-[(Z)-pentadec-9-enoxy]-2-propanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-tetradec-9-enoxy]propan-2-yl] heptanoate
[2-butanoyloxy-3-[(Z)-tetradec-9-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-hexadec-9-enoxy]propan-2-yl] pentanoate
[1-[2-aminoethoxy(hydroxy)phosphoryl]oxy-3-[(Z)-octadec-9-enoxy]propan-2-yl] propanoate
[(2R)-2-hydroxy-3-[(E)-octadec-6-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2R)-2-hydroxy-3-[(E)-octadec-4-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2R)-2-hydroxy-3-octadec-17-enoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2R)-2-hydroxy-3-[(E)-octadec-11-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2R)-2-hydroxy-3-[(E)-octadec-13-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
[(2R)-2-hydroxy-3-[(E)-octadec-7-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
2-Oleoyl-sn-glycero-3-phosphocholine
A lysophosphatidylcholine 18:1 in which the acyl group is specified as oleoyl and is located at position 2.
Lysophosphatidylcholine 18:1
A lysophosphatidylcholine in which the remaining acyl group (position not specified) contains 18 carbons with 1 double bond.
1-O-Oleoyl-sn-glycero-3-phosphocholine
An oleoyl-sn-glycero-3-phosphocholine in which the acyl group at position 1 is (9Z)-octadecenoyl (oleoyl) and the hydroxy group at position 2 is unsubstituted. A lysophosphatidylcholine 18:1 in which the acyl group at position 1 is (9Z)-octadecenoyl and the hydroxy group at position 2 is unsubstituted.
lysophosphatidylcholine (18:1/0:0)
A lysophosphatidylcholine 18:1 in which the acyl group is located at position 1.
lysophosphatidylcholine (0:0/18:1)
A lysophosphatidylcholine 18:1 in which the acyl group is located at position 2.
oleoyl-sn-glycero-3-phosphocholine
A lysophosphatidylcholine 18:1 in which the acyl group is specified as oleoyl and is located at either position 1 or 2.
1-[(9Z)-hexadecenyl]-2-acetyl-sn-glycero-3-phosphocholine
A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine in which the alkyl group is specified as (9Z)-hexadecenyl.
1-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine
A lysophosphatidylcholine 18:1 in which the acyl group specified as position 1 is (11Z)-octadecenoyl.
MePC(17:1)
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