Showing metabocard for LysoPC(22:5(4Z,7Z,10Z,13Z,16Z)) (LMDB00537)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:03 UTC
Update Date2016-07-20 21:04:13 UTC
LmdbLMDB00537
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(22:5(4Z,7Z,10Z,13Z,16Z))
DescriptionLysoPC(22:5(4Z,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(22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of docosapentaenoic acid at the C-1 position. The docosapentaenoic acid moiety is derived from animal fats and brain. 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-Docosapentaenoyl-glycero-3-phosphocholineChEBI
1-Docosapentaenoyl-GPCChEBI
1-Docosapentaenoyl-GPC (22:5n6)ChEBI
1-Osbondoyl-glycero-3-phosphocholineChEBI
GPC(22:5n6)ChEBI
LPC 22:5(4Z,7Z,10Z,13Z,16Z)/0:0ChEBI
LPC(22:5(4Z,7Z,10Z,13Z,16Z)/0:0)ChEBI
LysoPC 22:5(4Z,7Z,10Z,13Z,16Z)/0:0ChEBI
Lysophosphatidylcholine(22:5(4Z,7Z,10Z,13Z,16Z)/0:0)ChEBI
PC 22:5(4Z,7Z,10Z,13Z,16Z)/0:0ChEBI
PC(22:5(4Z,7Z,10Z,13Z,16Z)/0:0)ChEBI
PC(22:5n6)ChEBI
LPC(22:5)HMDB
LPC(22:5/0:0)HMDB
LPC(22:5n6/0:0)HMDB
LPC(22:5W6/0:0)HMDB
LyPC(22:5)HMDB
LyPC(22:5/0:0)HMDB
LyPC(22:5n6/0:0)HMDB
LyPC(22:5W6/0:0)HMDB
LysoPC(22:5)HMDB
LysoPC(22:5/0:0)HMDB
LysoPC(22:5n6/0:0)HMDB
LysoPC(22:5W6/0:0)HMDB
Lysophosphatidylcholine(22:5)HMDB
Lysophosphatidylcholine(22:5/0:0)HMDB
Lysophosphatidylcholine(22:5n6/0:0)HMDB
Lysophosphatidylcholine(22:5W6/0:0)HMDB
LysoPC(22:5(4Z,7Z,10Z,13Z,16Z))HMDB
1-(4Z,7Z,10Z,13Z,16Z-Docosapentaenoyl)-glycero-3-phosphocholineHMDB
1-DocosapentaenoylglycerophosphocholineHMDB
1-OsbondoylglycerophosphocholineHMDB
LysoPC(22:5(4Z,7Z,10Z,13Z,16Z)/0:0)ChEBI
Chemical FormulaC30H52NO7P
Average Molecular Weight569.7101
Monoisotopic Molecular Weight569.348139535
IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C30H52NO7P/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/h9-10,12-13,15-16,18-19,21-22,29,32H,5-8,11,14,17,20,23-28H2,1-4H3/b10-9-,13-12-,16-15-,19-18-,22-21-/t29-/m1/s1
InChI KeyYBUXFQUGNPBZPS-YNBHEIDWSA-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
logP2.86ALOGPS
logP2.05ChemAxon
logS-6.5ALOGPS
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 Count25ChemAxon
Refractivity175.46 m³·mol⁻¹ChemAxon
Polarizability63.59 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, Positivesplash10-008a-5952200000-3d72414a722a859e2abaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03ki-9432012000-4efc58ed8a3f1b3ecd20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(22:5(4Z,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, Positivesplash10-000i-9125130000-0dfca3f14d1c38ab69d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9357010000-a087fc3ba06af81c74c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9032000000-ac70dbd3eaa65fee169aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02vi-0009140000-43898f3935d98efbefd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0019100000-14b2479d10abb614d47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5129000000-f059575cf85aba53b54dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-d3a448ba125a1d0c601bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-679d7ca4b87c9ad34b9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-822ce24804b35ab1bc67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-9157bb4ea7537c0f0d37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0001090000-577f31cecd946342d9d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309040000-5fa1f20139316d5e9d40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-d19ac52f6fdee18f18baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000090000-6e5cfc43d4f6c4170e27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1601790000-6b8abe8133d3bcfb94f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000039000-0db65398a1e2c7312322Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0009016000-591393aae2d684545397Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0039011000-0f2b69851f9700bff3f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0003090000-8a59119df0de9c85c570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1009010000-ba11d5cd6b364aef6f5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1009000000-bfdb63fe967da11007c8Spectrum
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 IDHMDB0010402
FooDB IDFDB027553
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID PHOSPHATIDYLCHOLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766537
ChEBI ID74348
PubChem Compound ID53480473
Kegg Compound IDC04230
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available