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Record Information
Version3.6
Creation Date2008-10-29 08:32:00 UTC
Update Date2016-02-11 01:20:12 UTC
HMDB IDHMDB11128
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(0:0/18:0)
DescriptionLysoPC(0:0/18:0) or LPC(0:0/18:0) 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. Some LPLs serve important signaling functions such as lysophosphatidic acid. 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.LysoPC(0:0/18:0) has been shown to be protective against lethal sepsis in experimental animals by various mechanisms, including stimulation of neutrophils to eliminate invading pathogens through a peroxide-dependent reaction.
Structure
Thumb
Synonyms
ValueSource
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
2-Octadecanoyl-sn-glycero-3-phosphocholineChEBI
2-StearoyllysophosphatidylcholineChEBI
LPC (18:0)ChEBI
PC(0:0/18:0)ChEBI
Stearoyl lysophosphatidylcholineChEBI
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Hydroxy-2-stearoyl-sn-glycero-3-phosphocholineHMDB
LysophosphatidylcholineHMDB
Chemical FormulaC26H54NO7P
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
IUPAC Name(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1
InChI KeyInChIKey=IQGPMZRCLCCXAG-RUZDIDTESA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent2-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 2-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Fatty acid ester
  • Choline
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Cell signalling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000219 mg/mLALOGPS
logP2.5ALOGPS
logP2.08ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.48 m3·mol-1ChemAxon
Polarizability62.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027907
KNApSAcK IDNot Available
Chemspider ID24766523
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11128
Metagene LinkHMDB11128
METLIN IDNot Available
PubChem Compound24779491
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in sugar binding
Specific function:
May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:
CLC
Uniprot ID:
Q05315
Molecular weight:
16452.785
General function:
Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:
Modulates the action of platelet-activating factor (PAF) by hydrolyzing the sn-2 ester bond to yield the biologically inactive lyso-PAF. Has a specificity for substrates with a short residue at the sn-2 position. It is inactive against long-chain phospholipids.
Gene Name:
PLA2G7
Uniprot ID:
Q13093
Molecular weight:
50076.99
General function:
Involved in hydrolase activity
Specific function:
Inactivates paf by removing the acetyl group at the sn-2 position. This is a catalytic subunit. Plays an important role during the development of brain.
Gene Name:
PAFAH1B3
Uniprot ID:
Q15102
Molecular weight:
25734.13
General function:
Involved in hydrolase activity
Specific function:
Inactivates PAF by removing the acetyl group at the sn-2 position. This is a catalytic subunit.
Gene Name:
PAFAH1B2
Uniprot ID:
P68402
Molecular weight:
22733.715
General function:
Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:
Has a marked selectivity for phospholipids with short acyl chains at the sn-2 position. May share a common physiologic function with the plasma-type enzyme.
Gene Name:
PAFAH2
Uniprot ID:
Q99487
Molecular weight:
44035.255
General function:
Involved in 1-acylglycerophosphocholine O-acyltransfera
Specific function:
Acyltransferase which mediates the conversion of lysophosphatidylcholine (1-acyl-sn-glycero-3-phosphocholine or LPC) into phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine or PC) (LPCAT activity). Catalyzes also the conversion of lysophosphatidylserine (1-acyl-2-hydroxy-sn-glycero-3-phospho-L-serine or LPS) into phosphatidylserine (1,2-diacyl-sn-glycero-3-phospho-L-serine or PS) (LPSAT activity). Has also weak lysophosphatidylethanolamine acyltransferase activity (LPEAT activity). Favors polyunsaturated fatty acyl-CoAs as acyl donors compared to saturated fatty acyl-CoAs. Seems to be the major enzyme contributing to LPCAT activity in the liver. Lysophospholipid acyltransferases (LPLATs) catalyze the reacylation step of the phospholipid remodeling pathway also known as the Lands cycle.
Gene Name:
LPCAT3
Uniprot ID:
Q6P1A2
Molecular weight:
56034.48
General function:
Involved in acyltransferase activity
Specific function:
Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:
LPCAT1
Uniprot ID:
Q8NF37
Molecular weight:
59150.675
General function:
Involved in acyltransferase activity
Specific function:
Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-dependent. Involved in platelet-activating factor (PAF) biosynthesis by catalyzing the conversion of the PAF precursor, 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) into 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF). Also converts lyso-PAF to 1-alkyl-phosphatidylcholine (PC), a major component of cell membranes and a PAF precursor. Under resting conditions, acyltransferase activity is preferred. Upon acute inflammatory stimulus, acetyltransferase activity is enhanced and PAF synthesis increases (By similarity).
Gene Name:
LPCAT2
Uniprot ID:
Q7L5N7
Molecular weight:
60207.295
General function:
Involved in asparaginase activity
Specific function:
Exhibits lysophospholipase, transacylase, PAF acetylhydrolase and asparaginase activities.
Gene Name:
ASPG
Uniprot ID:
Q86U10
Molecular weight:
60882.4
General function:
Involved in hydrolase activity
Specific function:
Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:
PLB1
Uniprot ID:
Q6P1J6
Molecular weight:
161711.9