Showing metabocard for Arachidonyl lysolecithin (LMDB01018)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-08-06 05:39:49 UTC
Update Date2016-08-06 20:10:47 UTC
LmdbLMDB01018
Secondary Accession NumbersNone
Metabolite Identification
Common NameArachidonyl lysolecithin
DescriptionLysoPC(20:4(5Z,8Z,11Z,14Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl chain. 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(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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
ValueSource
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Arachidonoyl-glycero-3-phosphocholineChEBI
1-Arachidonoyl-GPCChEBI
GPC(20:4n6)ChEBI
LPC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
LPC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
LysoPC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
Lysophosphatidylcholine(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
PC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
PC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
LPC(20:4)HMDB
LPC(20:4/0:0)HMDB
LPC(20:4n6/0:0)HMDB
LPC(20:4W6/0:0)HMDB
LyPC(20:4)HMDB
LyPC(20:4/0:0)HMDB
LyPC(20:4n6/0:0)HMDB
LyPC(20:4W6/0:0)HMDB
LysoPC a C20:4HMDB
LysoPC(20:4)HMDB
LysoPC(20:4/0:0)HMDB
LysoPC(20:4n6/0:0)HMDB
LysoPC(20:4W6/0:0)HMDB
Lysophosphatidylcholine(20:4)HMDB
Lysophosphatidylcholine(20:4/0:0)HMDB
Lysophosphatidylcholine(20:4n6/0:0)HMDB
Lysophosphatidylcholine(20:4W6/0:0)HMDB
LysoPC(20:4(5Z,8Z,11Z,14Z))HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycero-3-phosphocholineHMDB
1-ArachidonoylglycerophosphocholineHMDB
LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
Chemical FormulaC28H50NO7P
Average Molecular Weight543.6729
Monoisotopic Molecular Weight543.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=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/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t27-/m1/s1
InChI KeyLAXQYRRMGGEGOH-JXRLJXCWSA-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
logP2.45ALOGPS
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
Polarizability60.98 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 (Non-derivatized) - 70eV, Positivesplash10-05aj-5960300000-0ee5b67c6a037e94173aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0feu-9441012000-f0e3e2a8c8b160e8afdbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9153130000-d52f673521111b5098b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-8394010000-35345158b0e85dd92443Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9041000000-d2cf76f6124369da1f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-0079170000-3ec998bd7f23091d2628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0059200000-813e63ff71fa72c208d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-9288000000-186fc82c9c4a804dd090Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003090000-b80221808526fa6e94a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1019010000-00330118424346f5754bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1009000000-235bb8cd3066c2669beaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-77ea54490e84a8b3b537Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udo-0002990000-bf882252024772103db4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4l-0309400000-b3d902f7c0961b2949cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000090000-b4c66c94aa69a4a40271Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0900060000-53fafe765bf1daa88e60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-0910040000-d12a6e3ffba0751a322dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-3472f30822b8e8601036Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0000090000-36674ea865affe2dc312Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609090000-dfdd3aa00d18d17c8130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-0fde8b52b527d51cb487Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0009070000-40ae7eb8536816f65fefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0039030000-a665ab26fc9f4e63275eSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Sun Ming-Qian, Li...
 details
DrugBank IDNot Available
HMDB IDHMDB0010395
FooDB IDFDB027546
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID PHOSPHATIDYLCHOLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21403155
ChEBI ID74344
PubChem Compound ID24779476
Kegg Compound IDC04230
YMDB IDYMDB02213
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available