ChemFOnt: Showing chemical card for LysoPC(26:1(5Z)/0:0) (CFc000010466)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:55 UTC

Chemfont ID

CFc000010466

Molecule Identification

Common Name

LysoPC(26:1(5Z)/0:0)

Definition

Lysopc(26:1(5z)), also known as LysoPC a C26:1, is classified as a member of the 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. Lysopc(26:1(5z)) is considered to be a practically insoluble (in water) and a moderately acidic compound. Lysopc(26:1(5z)) can be found in blood. Within a cell, Lysopc(26:1(5z)) is primarily located near the membrane (predicted from logp). 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
LysoPC a C26:1	HMDB

Chemical Formula

C₃₄H₆₈NO₇P

Average Molecular Weight

633.88

Monoisotopic Molecular Weight

633.473340047

IUPAC Name

(2-{[(2R)-3-[(5E)-hexacos-5-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(5E)-hexacos-5-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCC\C=C\CCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C34H68NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-34(37)40-31-33(36)32-42-43(38,39)41-30-29-35(2,3)4/h24-25,33,36H,5-23,26-32H2,1-4H3/b25-24+/t33-/m1/s1

InChI Key

HHNUOPXCCKOIPL-VTFFUMFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 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

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-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
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 28278231)

Excreta

Biofluid or Excreta

Feces (PMID: 27624970)
Urine (PMID: 32340350)

Cellular substructure

Membrane (HMDB: HMDB0029220)
Cell membrane (PMID: 30845751)

Cell

All cells and tissues (HMDB: HMDB0029220)

Source

Endogenous

Endogenous (HMDB: HMDB0029220)

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	4.9e-05 g/L	ALOGPS
logP	4.67	ALOGPS
logP	5.28	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	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	33	ChemAxon
Refractivity	189.4 m³·mol⁻¹	ChemAxon
Polarizability	78.51 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

HMDB0029220

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031405

KNApSAcK ID

Not Available

Chemspider ID

35032839

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for LysoPC(26:1(5Z)/0:0) (CFc000010466)

MOL for CFc000010466 (LysoPC(26:1(5Z)/0:0))

3D MOL for CFc000010466 (LysoPC(26:1(5Z)/0:0))

3D SDF for CFc000010466 (LysoPC(26:1(5Z)/0:0))

3D-SDF for CFc000010466 (LysoPC(26:1(5Z)/0:0))

PDB for CFc000010466 (LysoPC(26:1(5Z)/0:0))

3D PDB for CFc000010466 (LysoPC(26:1(5Z)/0:0))

SMILES for CFc000010466 (LysoPC(26:1(5Z)/0:0))

INCHI for CFc000010466 (LysoPC(26:1(5Z)/0:0))

Structure for CFc000010466 (LysoPC(26:1(5Z)/0:0))

3D Structure for CFc000010466 (LysoPC(26:1(5Z)/0:0))