Identification
YMDB IDYMDB02212
NameLysoPC(18:2(9Z,12Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(18:2(9Z,12Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. 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.
Structure
Thumb
Synonyms
  • 1-linoleoyl-glycero-3-phosphocholine
  • LPC(18:2)
  • LPC(18:2/0:0)
  • LPC(18:2n6/0:0)
  • LPC(18:2w6/0:0)
  • LyPC(18:2)
  • LyPC(18:2/0:0)
  • LyPC(18:2n6/0:0)
  • LyPC(18:2w6/0:0)
  • LysoPC(18:2)
  • LysoPC(18:2/0:0)
  • LysoPC(18:2n6/0:0)
  • LysoPC(18:2w6/0:0)
  • Lysophosphatidylcholine(18:2/0:0)
  • Lysophosphatidylcholine(18:2n6/0:0)
  • Lysophosphatidylcholine(18:2w6/0:0)
  • Lysophosphatidylcholine(18:2)
  • 1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholine
  • 1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholine
  • 1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholine
  • 1-18:2-LysoPC
  • 1-Linoleoyl-glycero-3-phosphocholine
  • 1-Linoleoyl-GPC
  • 1-Linoleoyl-GPC (18:2)
  • 1-Linoleoylglycerophosphocholine
  • GPC(18:2)
  • GPC(18:2/0:0)
  • LPC 18:2(9Z,12Z)/0:0
  • LPC(18:2)
  • LPC(18:2/0:0)
  • LPC(18:2n6/0:0)
  • LPC(18:2Omega6/0:0)
  • LyPC(18:2)
  • LyPC(18:2n6/0:0)
  • LyPC(18:2omega6/0:0)
  • LysoPC 18:2(9Z,12Z)/0:0
  • LysoPC(18:2)
  • LysoPC(18:2/0:0)
  • LysoPC(18:2n6/0:0)
  • LysoPC(18:2omega6/0:0)
  • Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)
  • Lysophosphatidylcholine(18:2/0:0)
  • Lysophosphatidylcholine(18:2n6/0:0)
  • Lysophosphatidylcholine(18:2omega6/0:0)
  • PC 18:2(9Z,12Z)/0:0
  • PC(18:2(9Z,12Z)/0:0)
  • LyPC(18:2/0:0)
  • LysoPC(18:2(9Z,12Z))
  • 1-Linoleoyl lysolecithin
  • 1-Linoleoyl-sn-glycero-3-phosphorylcholine
  • 1-Linoleoylglycerol-3-phosphorylcholine
  • 1-Linoleoylphosphatidylcholine
  • Linoleoyllysolecithin
  • Linoleyl lysophosphatidylcholine
  • Lysophosphatidylcholine 18:2
  • 1-Linoleoyl-lysophosphatidylcholine
  • 1-Linoleoyl-sn-glycero-3-phosphocholine
  • GPC(18:2(9Z,12Z))
  • GPC(18:2(9Z,12Z)/0:0)
  • GPC(18:2n6)
  • GPC(18:2n6/0:0)
  • GPC(18:2W6)
  • GPC(18:2W6/0:0)
  • LPC(18:2(9Z,12Z))
  • LPC(18:2(9Z,12Z)/0:0)
  • LPC(18:2n6)
  • LPC(18:2W6)
  • LPC(18:2W6/0:0)
  • LysoPC(18:2n6)
  • LysoPC(18:2W6)
  • LysoPC(18:2W6/0:0)
  • Lysophosphatidylcholine(18:2(9Z,12Z))
  • Lysophosphatidylcholine(18:2n6)
  • Lysophosphatidylcholine(18:2W6)
  • Lysophosphatidylcholine(18:2W6/0:0)
  • LysoPC(18:2(9Z,12Z)/0:0)
CAS numberNot Available
WeightAverage: 519.6515
Monoisotopic: 519.332489471
InChI KeySPJFYYJXNPEZDW-RUZDIDTESA-N
InChIInChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/t25-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC26H50NO7P
SMILESCCCCCC=CCC=CCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-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
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00026 g/LALOGPS
logP2.22ALOGPS
logP1.36ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.137 ± 0.00685 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-3c86eb832bb0e5b457ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-61bb2de3bf360b7c5784JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-703f583c1dec34d85363JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-971f1431e3c2228b9f5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-dd4dca9634d21e863fe4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-75b3d9cd99357a630043JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-9b4f9f161f1e634d70b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-2378656ce1b1501e42dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-ed0e0c463537d6bd8f93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-85bff21ad2f9c91a7447JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-38c8f8d665d29a310286JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e08a75389116b197e774JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7d81a037787f63d95855JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-6e0343e152dc3c713a98JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-20568d21d5462d55a6c0JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28733
HMDB IDHMDB10386
Pubchem Compound ID11005824
Kegg IDC04230
ChemSpider ID24823010
FOODB IDFDB030316
Wikipedia IDNot Available
BioCyc IDNot Available