Showing metabocard for LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (LMDB00538)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:05 UTC
Update Date2018-04-30 21:14:53 UTC
LmdbLMDB00538
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionLysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position. The docosahexaenoic 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Docosahexaenoyl-glycero-3-phosphocholineChEBI
LPC 22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0ChEBI
LPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
Lyso(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
LysoPC 22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0ChEBI
Lysophosphatidylcholine(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)ChEBI
LPC(22:6)HMDB
LPC(22:6/0:0)HMDB
LPC(22:6n3/0:0)HMDB
LPC(22:6W3/0:0)HMDB
LyPC(22:6)HMDB
LyPC(22:6/0:0)HMDB
LyPC(22:6n3/0:0)HMDB
LyPC(22:6W3/0:0)HMDB
LysoPC(22:6)HMDB
LysoPC(22:6/0:0)HMDB
LysoPC(22:6n3/0:0)HMDB
LysoPC(22:6W3/0:0)HMDB
Lysophosphatidylcholine(22:6)HMDB
Lysophosphatidylcholine(22:6/0:0)HMDB
Lysophosphatidylcholine(22:6n3/0:0)HMDB
Lysophosphatidylcholine(22:6W3/0:0)HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-glycero-3-phosphocholineHMDB
LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
1-DocosahexaenoylglycerophosphocholineHMDB
1-Docosahexaenoyl-GPCHMDB
1-Docosahexaenoyl-lysophosphatidylcholineHMDB
1-Docosahexaenoyl-sn-glycero-3-phosphocholineHMDB
DHA lysophosphatidylcholineHMDB
GPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
GPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)HMDB
GPC(22:6)HMDB
GPC(22:6n3)HMDB
GPC(22:6n3/0:0)HMDB
GPC(22:6W3)HMDB
GPC(22:6W3/0:0)HMDB
LPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
LPC(22:6n3)HMDB
LPC(22:6W3)HMDB
LysoPC(22:6n3)HMDB
LysoPC(22:6W3)HMDB
Lysophosphatidylcholine(22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB
Lysophosphatidylcholine(22:6n3)HMDB
Lysophosphatidylcholine(22:6W3)HMDB
LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)HMDB
Chemical FormulaC30H50NO7P
Average Molecular Weight567.6943
Monoisotopic Molecular Weight567.332489471
IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C30H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h6-7,9-10,12-13,15-16,18-19,21-22,29,32H,5,8,11,14,17,20,23-28H2,1-4H3/b7-6-,10-9-,13-12-,16-15-,19-18-,22-21-/t29-/m1/s1
InChI KeyLSOWKZULVQWMLY-APPDJCNMSA-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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.53ALOGPS
logP1.69ChemAxon
logS-6.4ALOGPS
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
Refractivity176.58 m³·mol⁻¹ChemAxon
Polarizability63.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0230-9433002000-b5fd41e28ea4799a79c2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-e8bef32951c9eda16960Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01i0-0001090000-abe804b0d09d64c91508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309040000-3a407c5e1234e91b87afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-2b92165957071e6b3cb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1006190000-af60ed4bf75afc22985dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0109000000-2c24525447e59647ca0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-e0399259b48327bfbf18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000090000-ba3d2d750970a47570b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1601790000-94e057a242a4c7624eb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000039000-6a99405facca5a64946fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0009016000-ddefb625d8a0fb8adaa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0039011000-dd78aa05e305d8717a4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000090000-67d3c276526724465aa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900060000-263d51168fd28cd1c380Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-ede15eec0297df860927Spectrum
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Sergio Polakof, D...
 details
DrugBank IDNot Available
HMDB IDHMDB0010404
FooDB IDFDB027555
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID PHOSPHATIDYLCHOLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8590975
ChEBI ID73873
PubChem Compound ID10415542
Kegg Compound IDC04230
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available