Showing metabocard for PC(22:4(7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)) (LMDB00518)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:38 UTC
Update Date2016-07-20 21:01:46 UTC
LmdbLMDB00518
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(22:4(7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z))
DescriptionPC(22:4(7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:4(7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z)), in particular, consists of one chain of adrenic acid at the C-1 position and one chain of mead acid at the C-2 position. The adrenic acid moiety is derived from animal fats, while the mead acid moiety is derived from fish oils, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Adrenoyl-2-meadoyl-sn-glycero-3-phosphocholineHMDB
GPCho(42:7)HMDB
Phosphatidylcholine(22:4/20:3)HMDB
PC(42:7)HMDB
LecithinHMDB
GPCho(22:4/20:3)HMDB
PC(22:4/20:3)HMDB
1-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(42:7)HMDB
PC(22:4(7Z,10Z,13Z,16Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC50H86NO8P
Average Molecular Weight860.1935
Monoisotopic Molecular Weight859.609105245
IUPAC Name(2-{[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C50H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-28-30-32-34-36-38-40-42-49(52)56-46-48(47-58-60(54,55)57-45-44-51(3,4)5)59-50(53)43-41-39-37-35-33-31-29-26-23-21-19-17-15-13-11-9-7-2/h14,16,20-23,25,27,29-32,35,37,48H,6-13,15,17-19,24,26,28,33-34,36,38-47H2,1-5H3/b16-14-,22-20-,23-21-,27-25-,31-29-,32-30-,37-35-/t48-/m1/s1
InChI KeyTVFZCOGIQILUFS-LNKIIHJVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP6.21ALOGPS
logP10.03ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity269.69 m³·mol⁻¹ChemAxon
Polarizability102.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-15b1c1efeca130176d72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-1bf9301d22c51cce565fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-1900041030-221cb4f12581689432f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-f962fc94dcc7517ba6beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000090-026be09b385c4028e7e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0100197030-a5ebc075f3188a032f34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-175d4e9cdcb782cbd5e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019004370-7d86d9162507a89c677dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-5109300000-abb4a45c7e943a4ea866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-313e864a8a4543f87d7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-21723311ec5e149bb2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041030-8f4a4cafc5bbde0664d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-781e4cb18f413ae935feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0003000090-32b40efeb851bdd8a67eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a66-0009000040-f3057d437fce536d7317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-df576825f79d2a98cfa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-4bcfbb1cefe522c6780bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900179030-cb411b00431bf1c9681bSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0008638
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53479253
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available