LysoPC(18:2(9Z,12Z)) (CHEM022740)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:50:17 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022740
Identification
Common NameLysoPC(18:2(9Z,12Z))
ClassSmall Molecule
DescriptionLysopc(18:2(9Z,12Z)), also known as LPC 18:2(9Z,12Z)/0:0 or LPC(18:2n6/0:0), 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. Thus, lysopc(18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. Lysopc(18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lysopc(18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1-18:2-LysoPCChEBI
1-Linoleoyl-glycero-3-phosphocholineChEBI
1-Linoleoyl-GPCChEBI
1-Linoleoyl-GPC (18:2)ChEBI
1-LinoleoylglycerophosphocholineChEBI
GPC(18:2)ChEBI
GPC(18:2/0:0)ChEBI
LPC 18:2(9Z,12Z)/0:0ChEBI
LPC(18:2)ChEBI
LPC(18:2/0:0)ChEBI
LPC(18:2n6/0:0)ChEBI
LPC(18:2Omega6/0:0)ChEBI
LyPC(18:2)ChEBI
LyPC(18:2n6/0:0)ChEBI
LyPC(18:2omega6/0:0)ChEBI
LysoPC 18:2(9Z,12Z)/0:0ChEBI
LysoPC(18:2)ChEBI
LysoPC(18:2/0:0)ChEBI
LysoPC(18:2n6/0:0)ChEBI
LysoPC(18:2omega6/0:0)ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)ChEBI
Lysophosphatidylcholine(18:2)ChEBI
Lysophosphatidylcholine(18:2/0:0)ChEBI
Lysophosphatidylcholine(18:2n6/0:0)ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)ChEBI
PC 18:2(9Z,12Z)/0:0ChEBI
PC(18:2(9Z,12Z)/0:0)ChEBI
LyPC(18:2/0:0)HMDB
LysoPC(18:2(9Z,12Z))HMDB
1-Linoleoyl lysolecithinHMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Linoleoylglycerol-3-phosphorylcholineHMDB
1-LinoleoylphosphatidylcholineHMDB
LinoleoyllysolecithinHMDB
Linoleyl lysophosphatidylcholineHMDB
Lysophosphatidylcholine 18:2HMDB
1-Linoleoyl-lysophosphatidylcholineHMDB
1-Linoleoyl-sn-glycero-3-phosphocholineHMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2(9Z,12Z)/0:0)HMDB
GPC(18:2n6)HMDB
GPC(18:2n6/0:0)HMDB
GPC(18:2W6)HMDB
GPC(18:2W6/0:0)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2(9Z,12Z)/0:0)HMDB
LPC(18:2n6)HMDB
LPC(18:2W6)HMDB
LPC(18:2W6/0:0)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2W6)HMDB
LysoPC(18:2W6/0:0)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2W6)HMDB
Lysophosphatidylcholine(18:2W6/0:0)HMDB
LysoPC(18:2(9Z,12Z)/0:0)ChEBI
Chemical FormulaC26H50NO7P
Average Molecular Mass519.652 g/mol
Monoisotopic Mass519.332 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
SMILESCCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
InChI IdentifierInChI=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/b10-9-,13-12-/t25-/m1/s1
InChI KeySPJFYYJXNPEZDW-FTJOPAKQSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-3c86eb832bb0e5b457ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-61bb2de3bf360b7c5784Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-703f583c1dec34d85363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-971f1431e3c2228b9f5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-dd4dca9634d21e863fe4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-75b3d9cd99357a630043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-9b4f9f161f1e634d70b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-2378656ce1b1501e42dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-ed0e0c463537d6bd8f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-85bff21ad2f9c91a7447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-38c8f8d665d29a310286Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e08a75389116b197e774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7d81a037787f63d95855Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-6e0343e152dc3c713a98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-20568d21d5462d55a6c0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0010386
FooDB IDFDB030316
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-8347
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9181014
ChEBI ID28733
PubChem Compound ID11005824
Kegg Compound IDNot Available
YMDB IDYMDB02212
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
2. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
8. Phospholipids Handbook
9. The lipid handbook with CD-ROM