LysoPC(20:4(8Z,11Z,14Z,17Z)) (YMDB02214)

Identification
YMDB IDYMDB02214
NameLysoPC(20:4(8Z,11Z,14Z,17Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(20:4(8Z,11Z,14Z,17Z)) 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(20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicsoatetraenoic acid at the C-1 position. The eicsoatetraenoic acid moiety is derived from fish 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
MOLSDFPDBSMILESInChI
Synonyms
  • 1-eicsoate
  • 1-eicsoatetraenoyl-glycero-3-phosphocholine
  • 1-eicsoic acid
  • LPC(20:4)
  • LPC(20:4/0:0)
  • LPC(20:4n3/0:0)
  • LPC(20:4w3/0:0)
  • LyPC(20:4)
  • LyPC(20:4/0:0)
  • LyPC(20:4n3/0:0)
  • LyPC(20:4w3/0:0)
  • LysoPC(20:4)
  • LysoPC(20:4/0:0)
  • LysoPC(20:4n3/0:0)
  • Lysophosphatidylcholine(20:4)
  • Lysophosphatidylcholine(20:4/0:0)
  • Lysophosphatidylcholine(20:4n3/0:0)
  • Lysophosphatidylcholine(20:4w3/0:0)
  • LysoPC(20:4w3/0:0)
  • 1-Eicsoatetraenoyl-glycero-3-phosphocholine
  • LPC(20:4/0:0)
  • LysoPC(20:4(8Z,11Z,14Z,17Z))
  • LysoPC(20:4/0:0)
  • Lysophosphatidylcholine(20:4/0:0)
  • 1-Eicsoate
  • 1-Eicsoic acid
  • LPC(20:4)
  • LPC(20:4n3/0:0)
  • LPC(20:4W3/0:0)
  • LyPC(20:4)
  • LyPC(20:4/0:0)
  • LyPC(20:4n3/0:0)
  • LyPC(20:4W3/0:0)
  • LysoPC a C20:4
  • LysoPC(20:4)
  • LysoPC(20:4n3/0:0)
  • Lysophosphatidylcholine(20:4)
  • Lysophosphatidylcholine(20:4n3/0:0)
  • Lysophosphatidylcholine(20:4W3/0:0)
  • 1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-glycero-3-phosphocholine
  • 1-Eicsoatetraenoylglycerophosphocholine
CAS numberNot Available
WeightAverage: 543.6729
Monoisotopic: 543.332489471
InChI KeyGOMVPVRDBLLHQC-HHHXNRCGSA-N
InChIInChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h6-7,9-10,12-13,15-16,27,30H,5,8,11,14,17-26H2,1-4H3/t27-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC28H50NO7P
SMILESCCC=CCC=CCC=CCC=CCCCCCCC(=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 Solubility0.00029 g/LALOGPS
logP2.41ALOGPS
logP1.52ChemAxon
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
Refractivity165.14 m³·mol⁻¹ChemAxon
Polarizability61.24 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
0.033 ± 0.00165 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 (Non-derivatized) - 70eV, Positivesplash10-05a2-4950200000-5f3ea1281b366fbf0bf0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0h2u-9631002000-548020bf93f9ae06ef9bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9153130000-d52f673521111b5098b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9383010000-e6c78f8dd918cdfd3908JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9041000000-8835fa70061dabb71b87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-0079170000-3ec998bd7f23091d2628JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0059200000-8a262b7e1a3a9274ec32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-9288000000-824a302e9a9fcf612010JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-77ea54490e84a8b3b537JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udo-0002990000-bf882252024772103db4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4l-0309400000-b3d902f7c0961b2949cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-3472f30822b8e8601036JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0000090000-36674ea865affe2dc312JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609090000-dfdd3aa00d18d17c8130JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-0fde8b52b527d51cb487JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0009070000-40ae7eb8536816f65fefJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0039030000-a665ab26fc9f4e63275eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003090000-6ea8042d7f2a61358243JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1029010000-b64d2c578dde5bd000a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1009000000-235bb8cd3066c2669beaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000090000-b4c66c94aa69a4a40271JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0900060000-53fafe765bf1daa88e60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-0910040000-d12a6e3ffba0751a322dJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86259
HMDB IDHMDB10396
Pubchem Compound ID53480469
Kegg IDC04230
ChemSpider ID24766532
FOODB IDFDB027547
Wikipedia IDNot Available
BioCyc IDNot Available