1-arachidonoylglycerophosphoinositol

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Name: 1-arachidonoylglycerophosphoinositol
Description: LysoPI(20:0/0:0) is a lysophosphatidylinositol. 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 t... he 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. Lysophosphatidylinositols 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. LysoPI(20:0/0:0), in particular, consists of one chain of arachidic acid at the C-1 position. (HMDB0240260)

Age group comparisons
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample
27374292	Age [25–35] (median=32), Gender ♂	0.994352 (mean value of the compound area)	LC/MS Neg	serum
27374292	Age [55-64] (median=60), Gender ♂	1.363652 (mean value of the compound area)	LC/MS Neg	serum

Linear regression
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample

log2 ratio/log2(FC)
PMID	Age/Age interval, Gender	Value (unit of measurement)	Method	Sample

Synonym:

PI(20:4(5Z,8Z,11Z,14Z)/0:0)
Chemical Formula:

C29H49O12P
Systematic name:

[(2R)-2-hydroxy-3-[hydroxy-[(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
SMILES:

CCCCCC=CCC=CCC=CCC=CCCCC(=O)OCC(COP(=O)(O)OC1C(C(C(C(C1O)O)O)O)O)O
InChI:

InChI=1S/C29H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(31)39-20-22(30)21-40-42(37,38)41-29-27(35)25(33)24(32)26(34)28(29)36/h6-7,9-10,12-13,15-16,22,24-30,32-36H,2-5,8,11,14,17-21H2,1H3,(H,37,38)/b7-6-,10-9-,13-12-,16-15-/t22-,24?,25-,26+,27-,28-,29?/m1/s1
InChI Key:

LXUGKKVCSTYZFK-VUSDMFPISA-N

Literature sources:
- Saito K et al., Gender- and Age-Associated Differences in Serum Metabolite Profiles among Japanese Populations., Biological & pharmaceutical bulletin, 1179-86, 2016
External links:

HMDB PubChem ChEBI

Metabolite location:

Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Serum, Tissue, Cellular (general class), Subcellular, Cell membrane, Intracellular membrane
Metabolite source:

Homo sapiens, endogenous metabolite

Age group comparisons

Method: LC/MS Neg

Sample: serum

PMID: 27374292