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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-10-29 14:26:36 UTC
Update Date2022-11-30 19:03:55 UTC
HMDB IDHMDB0011149
Secondary Accession Numbers
  • HMDB0062689
  • HMDB11149
  • HMDB62689
Metabolite Identification
Common NameLysoPC(O-18:0/0:0)
Description1-Octadecyl-sn-glycero-3-phosphocholine is an intermediate in the ether lipid metabolism pathway. 1-Octadecyl-sn-glycero-3-phosphocholine is irreversibly produced from 2-acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine via the enzyme 1-alkyl-2-acetylglycerophosphocholine esterase (EC 3.1.1.47). 1-Octadecyl-sn-glycero-3-phosphocholine is an ether phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol are bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. 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?1582752873
Synonyms
ValueSource
1-O-Octadecylglycerol-3-phosphatidylcholineHMDB
1-Octadecyl-sn-glycero-3-phosphocholineHMDB
1-Stearyl-GPCHMDB
1-Stearyl-GPC (O-18:0)HMDB
GPC(O-18:0)HMDB
GPC(O-18:0/0:0)HMDB
LPC (O-18:0)HMDB
LysoPC(18:0E/0:0)HMDB
LysoPC(O-18:0)HMDB
PC(O-18:0/0:0)HMDB
LysoPC(DM18:0)HMDB
1-O-Octadecyl-sn-glycero-3-phosphocholineHMDB
1-O-Octadecyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Octadecyl-GPCHMDB
1-Octadecyl-lysophosphatidylcholineHMDB
1-Octadecylglycero-3-phosphocholineHMDB
GPC(18:0)HMDB
GPC(18:0/0:0)HMDB
LPC(18:0)HMDB
LPC(18:0/0:0)HMDB
LPC(O-18:0)HMDB
LPC(O-18:0/0:0)HMDB
Lyso-platelet-activating factorHMDB
LysoPC(18:0)HMDB
LysoPC(18:0/0:0)HMDB
Lysophosphatidylcholine(18:0)HMDB
Lysophosphatidylcholine(18:0/0:0)HMDB
Lysophosphatidylcholine(O-18:0)HMDB
Lysophosphatidylcholine(O-18:0/0:0)HMDB
LysoPC(O-18:0/0:0)HMDB
Chemical FormulaC26H56NO6P
Average Molecular Weight509.6997
Monoisotopic Molecular Weight509.384525041
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number74430-89-0
SMILES
CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1
InChI KeyXKBJVQHMEXMFDZ-AREMUKBSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentMonoalkylglycerophosphocholines
Alternative Parents
Substituents
  • Monoalkylglycerophosphocholine
  • Phosphocholine
  • Glycerol ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic salt
  • 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 Solubility0.00027 g/LALOGPS
logP2.98ALOGPS
logP2.46ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.05 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.72 m³·mol⁻¹ChemAxon
Polarizability62.7 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]+233.64830932474
DeepCCS[M-H]-230.56130932474
DeepCCS[M-2H]-264.63630932474
DeepCCS[M+Na]+241.14530932474
AllCCS[M+H]+240.132859911
AllCCS[M+H-H2O]+238.832859911
AllCCS[M+NH4]+241.232859911
AllCCS[M+Na]+241.632859911
AllCCS[M-H]-234.432859911
AllCCS[M+Na-2H]-236.832859911
AllCCS[M+HCOO]-239.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPC(O-18:0/0:0)CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3398.2Standard polar33892256
LysoPC(O-18:0/0:0)CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3220.0Standard non polar33892256
LysoPC(O-18:0/0:0)CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3436.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPC(O-18:0/0:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C3393.2Semi standard non polar33892256
LysoPC(O-18:0/0:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3654.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(O-18:0/0:0) GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-5930000000-c002f9346ff27ec388a32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(O-18:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9460000000-f8bf856a15fd2cd2fa222017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Positive-QTOFsplash10-01p9-9123230000-9e5018d60ea3b2b28b322017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOFsplash10-0ugr-9455200000-0c72dc03f55ca1a4599e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOFsplash10-0f79-9231000000-adbce76401a5b20f74d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOFsplash10-0a4i-0010490000-78228db3f0e06f9d298c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOFsplash10-0ar0-2160920000-56a3704799b8868294e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOFsplash10-00or-9280000000-a127711d12f38e9034132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Positive-QTOFsplash10-001i-0000090000-92389686f000bb55e1132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOFsplash10-001i-0000090000-92389686f000bb55e1132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOFsplash10-00di-0000930000-3fa7cb0f3d40c52c6b6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOFsplash10-0a4i-0000090000-0092c5cfc59f1e835b622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOFsplash10-0a4i-0020290000-1cacf188cd006762529a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOFsplash10-004i-9210100000-3e2f6987fc891e79e2c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Negative-QTOFsplash10-0006-0000090000-ac3949a1bc7527be80e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Negative-QTOFsplash10-0006-0110690000-b1a4faf5ff77d30fbafc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Negative-QTOFsplash10-0006-0110910000-2f268286db3bc04e9cec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 10V, Positive-QTOFsplash10-0il0-1900160000-4dc04f9d727b989bed342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 20V, Positive-QTOFsplash10-0ik9-1710190000-87893f3898856e238ceb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(O-18:0/0:0) 40V, Positive-QTOFsplash10-0ik9-0710190000-487f87885e45a61ac64d2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027924
KNApSAcK IDNot Available
Chemspider ID2015318
KEGG Compound IDC04317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2733532
PDB IDNot Available
ChEBI ID75216
Food Biomarker OntologyNot Available
VMH IDAK2LGCHOL_HS
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 26 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
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 phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
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 phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1

Only showing the first 10 proteins. There are 26 proteins in total.