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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 08:32:00 UTC
Update Date2022-11-30 19:03:54 UTC
HMDB IDHMDB0011128
Secondary Accession Numbers
  • HMDB11128
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. 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
Data?1582752871
Synonyms
ValueSource
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateHMDB
2-Octadecanoyl-sn-glycero-3-phosphocholineHMDB
2-StearoyllysophosphatidylcholineHMDB
LPC (18:0)HMDB
PC(0:0/18:0)HMDB
Stearoyl lysophosphatidylcholineHMDB
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidHMDB
1-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Hydroxy-2-stearoyl-sn-glycero-3-phosphocholineHMDB
LysophosphatidylcholineHMDB
2-Stearoyl-glycero-3-phosphocholineHMDB
LysoPC(18:0)HMDB
LPC(0:0/18:0)HMDB
Lysophosphatidylcholine(0:0/18:0)HMDB
LyPC(0:0/18:0)HMDB
Lysophosphatidylcholine(18:0)HMDB
LPC(18:0)HMDB
LyPC(18:0)HMDB
2-Octadecanoyl-glycero-3-phosphocholineHMDB
2-OctadecanoylglycerophosphocholineHMDB
2-StearoylglycerophosphocholineHMDB
LysoPC(0:0/18:0)Lipid Annotator
Chemical FormulaC26H54NO7P
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
IUPAC Name(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number4421-58-3
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C
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 KeyIQGPMZRCLCCXAG-RUZDIDTESA-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.
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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.48 m³·mol⁻¹ChemAxon
Polarizability62.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+238.53130932474
DeepCCS[M-H]-235.95930932474
DeepCCS[M-2H]-269.52130932474
DeepCCS[M+Na]+246.02930932474
AllCCS[M+H]+240.732859911
AllCCS[M+H-H2O]+239.532859911
AllCCS[M+NH4]+241.832859911
AllCCS[M+Na]+242.132859911
AllCCS[M-H]-234.532859911
AllCCS[M+Na-2H]-237.032859911
AllCCS[M+HCOO]-239.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPC(0:0/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3426.0Standard polar33892256
LysoPC(0:0/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3216.9Standard non polar33892256
LysoPC(0:0/18:0)CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C3500.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPC(0:0/18:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C3484.5Semi standard non polar33892256
LysoPC(0:0/18:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)O[C@H](CO[Si](C)(C)C(C)(C)C)COP(=O)([O-])OCC[N+](C)(C)C3709.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(0:0/18:0) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fek-9550100000-80d62412107a36847bc72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(0:0/18:0) GC-MS (1 TMS) - 70eV, Positivesplash10-008a-9721020000-9b41f1bf1e3d5e7cf26c2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOFsplash10-0fc0-0900060000-e99379bc4ac53cc771472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOFsplash10-0ul0-0900050000-23f28f5f047f20928b272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOFsplash10-0ul0-0900050000-bfd773fc6fa74017c0dc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Positive-QTOFsplash10-000i-9071130000-2c3354f59d1c3ced0f442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOFsplash10-00n3-8292010000-d0e88a09c384d49429af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Positive-QTOFsplash10-002r-9130000000-de498d2cd72d4ce9e8ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Negative-QTOFsplash10-00e9-0070290000-bdddd2700d06c482f6d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Negative-QTOFsplash10-014r-2370920000-8d3fcd824e1c0856f6062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Negative-QTOFsplash10-00o0-6290000000-dabf6a0ad90d8af67ae62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Positive-QTOFsplash10-00di-1100090000-3808cd3b9510a0dec1282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Positive-QTOFsplash10-001i-2910020000-6397418d2fe7e18b74e42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Positive-QTOFsplash10-00dr-6900000000-b110314336110b4177952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 10V, Negative-QTOFsplash10-00di-0000090000-c3d13afe335d8b212b662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 20V, Negative-QTOFsplash10-0089-0090160000-c2b2361f52a0743ec66a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(0:0/18:0) 40V, Negative-QTOFsplash10-003r-8290200000-f73f39a5b22cf648489f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027907
KNApSAcK IDNot Available
Chemspider ID24766523
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779491
PDB IDNot Available
ChEBI ID76076
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
  7. Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
  8. Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]
  9. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 15 proteins in total.

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 G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for medium and long chain saturated and unsaturated fatty acids. Binding of the ligand increase intracellular calcium concentration and amplify glucose-stimulated insulin secretion. The activity of this receptor is mediated by G- proteins that activate phospholipase C. Seems to act through a G(q) and G(i)-mediated pathway
Gene Name:
FFAR1
Uniprot ID:
O14842
Molecular weight:
31456.6
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

Only showing the first 10 proteins. There are 15 proteins in total.