Common Name1-hexanoyl-sn-glycero-3-phosphocholine
DescriptionLysopc(6:0), also known as LPC(6:0/0:0) or 1-Caproyl-sn-glycero-3-phosphocholine, 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(6:0) is considered to be a practically insoluble (in water) and a moderately acidic compound. Lysopc(6:0) is a glycerophosphocholine lipid molecule. Lysopc(6:0) can be found in urine. 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
Molecular FormulaC14H30NO7P
Average Mass355.36430
Monoisotopic Mass355.17599
IUPAC Name(2-{[(2R)-3-(hexanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2r)-3-(hexanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILESCCCCCC(=O)OC[C@@H](O)COP(=O)([O-])OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C14H30NO7P/c1-5-6-7-8-14(17)20-11-13(16)12-22-23(18,19)21-10-9-15(2,3)4/h13,16H,5-12H2,1-4H3/t13-/m1/s1
InChI KeyWDNDPXJAUNUOFK-CYBMUJFWSA-N
CHEBI IDCHEBI:78215
HMDB IDHMDB0029207
StateNot Available
Water Solubility8.20e-01 g/l
logP-1.90
logS-2.70
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)-3.40
Hydrogen Acceptor Count4
Hydrogen Donor Count1
Polar Surface Area105.12 Ų
Rotatable Bond Count14
Physiological Charge0
Formal Charge0
Refractivity96.26 m³·mol⁻¹
Polarizability37.15

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