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Showing Compound LysoPC(O-18:0) (FDB027924)

Record Information
Version1.0
Creation date2011-09-21 01:32:04 UTC
Update date2015-07-21 06:59:16 UTC
Primary IDFDB027924
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(O-18:0)
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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1-O-Octadecyl-sn-glycero-3-ocholineChEBI
1-O-Octadecylglycerol-3-atidylcholineChEBI
1-Octadecyl-sn-glycero-3-ocholineChEBI
LysoPC(18:0e/0:0)hmdb
LysoPC(dm18:0)HMDB
LysoPC(o-18:0)LysoPC(dm18:0)hmdb
LysoPC(o-18:0/0:0)hmdb
Predicted 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
Chemical FormulaC26H56NO6P
IUPAC name(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight509.6997
Monoisotopic Molecular Weight509.384525041
Classification
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

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(O-18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-5930000000-c002f9346ff27ec388a3Spectrum
Predicted GC-MSLysoPC(O-18:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9460000000-f8bf856a15fd2cd2fa22Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9123230000-9e5018d60ea3b2b28b322017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ugr-9455200000-0c72dc03f55ca1a4599e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-9231000000-adbce76401a5b20f74d52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0010490000-78228db3f0e06f9d298c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar0-2160920000-56a3704799b8868294e22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9280000000-a127711d12f38e9034132017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-92389686f000bb55e1132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000090000-92389686f000bb55e1132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000930000-3fa7cb0f3d40c52c6b6a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-0092c5cfc59f1e835b622021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0020290000-1cacf188cd006762529a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210100000-3e2f6987fc891e79e2c02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-ac3949a1bc7527be80e62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0110690000-b1a4faf5ff77d30fbafc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0110910000-2f268286db3bc04e9cec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il0-1900160000-4dc04f9d727b989bed342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1710190000-87893f3898856e238ceb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ik9-0710190000-487f87885e45a61ac64d2021-09-22View Spectrum
NMRNot Available
ChemSpider ID2015318
ChEMBL IDCHEMBL475587
KEGG Compound IDC04317
Pubchem Compound ID2733532
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11149
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
60 kDa lysophospholipaseASPGQ86U10
Eosinophil lysophospholipaseCLCQ05315
Platelet-activating factor acetylhydrolasePLA2G7Q13093
Platelet-activating factor acetylhydrolase IB subunit gammaPAFAH1B3Q15102
Platelet-activating factor acetylhydrolase IB subunit betaPAFAH1B2P68402
Platelet-activating factor acetylhydrolase 2, cytoplasmicPAFAH2Q99487
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference