ChemFOnt: Showing chemical card for LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) (CFc000042115)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:44:27 UTC

Chemfont ID

CFc000042115

Molecule Identification

Common Name

LysoPC(0:0/20:4(5Z,8Z,11Z,14Z))

Definition

LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) 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(0:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-2 position. LPL-R's are members of the G protein-coupled receptor (GPR) family of integral membrane proteins. Lysophosphatidylcholines (LPCs) specifically bind to GPR119, GPR40, GPR55 and GPR4. binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins. Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin (PMID: 32599910 ). In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood. Hypoalbuminemia with albumin concentrations of <20 g/L are typical of patients with sepsis, burns or serious trauma (PMID: 26557421 ). Such low levels of albumin often lead to LPC levels that are 50-80 % lower than that seen in healthy individuals (PMID: 27501420 ). Decreased levels of LPC have been observed in a number of other inflammatory conditions beyond sepsis, including rheumatoid arthritis, diabetes, schizophrenia, polycystic ovary syndrome, Alzheimer’s disease, pulmonary arterial hypertension, aging, asthma and liver cirrhosis, where they were associated with increased mortality risk (PMID: 32599910 ). LPCs have a number of protective or anti-inflammatory effects. Higher levels of LPC induce cyclooxygenase-2 and endothelial nitric oxide synthase (eNOS) expression in endothelial cells, both of which can have vasoprotective effects either via production of prostacyclin or nitric oxide (PMID: 32599910 ). LPCs have been shown to elicit a number of effects on the innate immune system and effectively serve as dual-activity ligand molecules. In particular, LPCs directly activate toll-like receptor (TLR) 4 and TLR-2-1 receptors in the absence of classical TLR ligands. However, LPCs can also inhibit TLR-mediated signaling in the presence of classical TLR ligands, thereby acting as anti-inflammatory molecules (PMID: 32599910 ). Low levels of LPC during a bacterial or viral infection with TLR-mediated signalling can lead to opposing (inflammatory vs. anti-inflammatory) effects and immune dysregulation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphocholine	ChEBI
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphocholine	ChEBI
2-Arachidonoyl-GPC	ChEBI
2-Arachidonoyllysophosphatidylcholine	ChEBI
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-ALPC	MeSH
2-Arachidonoylglycero-3-phosphocholine	MeSH
2-Arachidonoyl-lysopc	MeSH
2-Arachidonoyl-lysophosphatidylcholine	HMDB
2-Arachidonoyl-sn-glycero-3-phosphocholine	HMDB
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(0:0/20:4(5Z,8Z,11Z,14Z))	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

Chemical Formula

C₂₈H₅₀NO₇P

Average Molecular Weight

543.682

Monoisotopic Molecular Weight

543.332489952

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 Number

67341-29-1

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 Key

IGJKYDBBINVMLH-JXRLJXCWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

2-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

2-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lysophosphatidylcholine 20:4 (CHEBI:76079 )
Monoacylglycerophosphocholines (LMGP01050121 )

Functional Ontology

All cells and tissues (HMDB: HMDB0061699)

Cellular substructure

Cell membrane (PMID: 30845751)

Source

Exogenous

Exogenous (HMDB: HMDB0061699)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 30845751)

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0003 g/L	ALOGPS
logP	2.41	ALOGPS
logP	1.52	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	165.14 m³·mol⁻¹	ChemAxon
Polarizability	60.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0061699

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21403158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52924038

PDB ID

Not Available

ChEBI ID

76079

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) (CFc000042115)

MOL for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

3D MOL for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

3D SDF for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

3D-SDF for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

PDB for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

3D PDB for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

SMILES for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

INCHI for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

Structure for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))

3D Structure for CFc000042115 (LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)))