Showing metabocard for LysoPC(22:4(7Z,10Z,13Z,16Z)) (LMDB00536)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:02 UTC
Update Date2016-07-20 21:04:13 UTC
LmdbLMDB00536
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(22:4(7Z,10Z,13Z,16Z))
DescriptionLysoPC(22:4(7Z,10Z,13Z,16Z)) 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(22:4(7Z,10Z,13Z,16Z)), in particular, consists of one chain of adrenic acid at the C-1 position. The adrenic acid moiety is derived from animal fats. 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-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-glycero-3-phosphocholineChEBI
1-Adrenoyl-glycero-3-phosphocholineChEBI
1-Adrenoyl-GPCChEBI
1-Adrenoyl-GPC (22:4)ChEBI
1-Adrenoyl-sn-glycero-3-phosphocholineChEBI
GPC(22:4)ChEBI
GPC(22:4/0:0)ChEBI
LPC(22:4(7Z,10Z,13Z,16Z)/0:0)ChEBI
LPC(22:4)ChEBI
LPC(22:4/0:0)ChEBI
LPC(22:4n6/0:0)ChEBI
LPC(22:4W6/0:0)ChEBI
LyPC(22:4)ChEBI
LyPC(22:4/0:0)ChEBI
LyPC(22:4n6/0:0)ChEBI
LyPC(22:4W6/0:0)ChEBI
LysoPC(22:4)ChEBI
LysoPC(22:4/0:0)ChEBI
LysoPC(22:4n6/0:0)ChEBI
LysoPC(22:4W6/0:0)ChEBI
Lysophosphatidylcholine(22:4)ChEBI
Lysophosphatidylcholine(22:4/0:0)ChEBI
Lysophosphatidylcholine(22:4n6/0:0)ChEBI
Lysophosphatidylcholine(22:4W6/0:0)ChEBI
PC(22:4(7Z,10Z,13Z,16Z)/0:0)ChEBI
LysoPC(22:4(7Z,10Z,13Z,16Z))HMDB
1-AdrenoylglycerophosphocholineHMDB
Chemical FormulaC30H54NO7P
Average Molecular Weight571.726
Monoisotopic Molecular Weight571.363789599
IUPAC Name(2-{[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C30H54NO7P/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/h9-10,12-13,15-16,18-19,29,32H,5-8,11,14,17,20-28H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t29-/m1/s1
InChI KeyZOJBSSVHFSBHMP-JJJSWPRASA-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
logP3.03ALOGPS
logP2.41ChemAxon
logS-6.6ALOGPS
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 Count26ChemAxon
Refractivity174.35 m³·mol⁻¹ChemAxon
Polarizability65.17 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, Positivesplash10-024u-9432012000-c1ea4b26504c04725c4eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(22:4(7Z,10Z,13Z,16Z)/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, Positivesplash10-004i-0000090000-9c2f07cddacd37b638c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0001090000-9cf5b92d1aeab3b5a936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frj-0309040000-11f90b2843a2cd4891b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-01fe2ec9d7eb15d6b4aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0000090000-48a51bbd4b5e4e7b0f4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1601790000-1947090a55dc8278ef51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0003090000-359626919977f632df6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1009010000-7718609651953c03c652Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1009000000-78b6d8058c705b640de4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-7282f84bb93138814d4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-31c3e53929caab2772acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-b41159c5d6a65ee1049fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000039000-aa4234fa1ba784c6332fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0009016000-261cd04940c1d0331f90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0039011000-c029b676a207f32d2a6cSpectrum
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 IDHMDB0010401
FooDB IDFDB027552
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID PHOSPHATIDYLCHOLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766536
ChEBI ID133657
PubChem Compound ID52924039
Kegg Compound IDC04230
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available