Record Information
Version1.0
StatusDetected and Quantified
Creation Date2023-01-31 22:25:52 UTC
Update Date2023-01-31 22:25:52 UTC
Metabolite IDMMDBc0060116
Metabolite Identification
Common NameLysoPC(0:0/20:4(5Z,8Z,11Z,14Z))
DescriptionLysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl chain. 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(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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.
Structure
Synonyms
ValueSource
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphocholineChEBI
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
2-Arachidonoyl-GPCChEBI
2-ArachidonoyllysophosphatidylcholineChEBI
GPC(0:0/20:4)ChEBI
GPC(20:4)ChEBI
LPC(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
PC(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
2-ALPCHMDB
2-Arachidonoylglycero-3-phosphocholineHMDB
2-Arachidonoyl-lysopcHMDB
2-Arachidonoyl-lysophosphatidylcholineHMDB
2-Arachidonoyl-sn-glycero-3-phosphocholineHMDB
GPC(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPC(0:0/20:4n6)HMDB
GPC(0:0/20:4W6)HMDB
GPC(20:4(5Z,8Z,11Z,14Z))HMDB
GPC(20:4n6)HMDB
GPC(20:4W6)HMDB
LPC(0:0/20:4n6)HMDB
LPC(0:0/20:4W6)HMDB
LPC(20:4(5Z,8Z,11Z,14Z))HMDB
LPC(20:4)HMDB
LPC(20:4n6)HMDB
LPC(20:4W6)HMDB
LysoPC(0:0/20:4n6)HMDB
LysoPC(0:0/20:4W6)HMDB
LysoPC(20:4(5Z,8Z,11Z,14Z))HMDB
LysoPC(20:4)HMDB
LysoPC(20:4n6)HMDB
LysoPC(20:4W6)HMDB
Lysophosphatidylcholine(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylcholine(0:0/20:4n6)HMDB
Lysophosphatidylcholine(0:0/20:4W6)HMDB
Lysophosphatidylcholine(20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylcholine(20:4)HMDB
Lysophosphatidylcholine(20:4n6)HMDB
Lysophosphatidylcholine(20:4W6)HMDB
LysoPC(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
Molecular FormulaC28H50NO7P
Average Mass543.682
Monoisotopic Mass543.332489952
IUPAC Name(2-{[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)36-27(25-30)26-35-37(32,33)34-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t27-/m1/s1
InChI KeyIGJKYDBBINVMLH-JXRLJXCWSA-N