Showing metabocard for PC(20:4(8Z,11Z,14Z,17Z)/14:0) (LMDB00513)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:32 UTC
Update Date2016-07-20 20:43:51 UTC
LmdbLMDB00513
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(20:4(8Z,11Z,14Z,17Z)/14:0)
DescriptionPC(20:4(8Z,11Z,14Z,17Z)/14:0) 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(20:4(8Z,11Z,14Z,17Z)/14:0), in particular, consists of one chain of eicsoatetraenoic acid at the C-1 position and one chain of myristic acid at the C-2 position. The eicsoatetraenoic acid moiety is derived from fish oils, while the myristic acid moiety is derived from nutmeg and butter. 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
GPCho(34:4)HMDB
PC(20:4/14:0)HMDB
Phosphatidylcholine(20:4/14:0)HMDB
PC(34:4)HMDB
LecithinHMDB
GPCho(20:4/14:0)HMDB
1-Eicsoatetraenoyl-2-myristoyl-sn-glycero-3-phosphocholineHMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-tetradecanoyl-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(34:4)HMDB
PC(20:4(8Z,11Z,14Z,17Z)/14:0)Lipid Annotator
Chemical FormulaC42H76NO8P
Average Molecular Weight754.0285
Monoisotopic Molecular Weight753.530854925
IUPAC Name(2-{[(2R)-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-24-17-15-13-11-9-7-2/h8,10,14,16,19-20,22-23,40H,6-7,9,11-13,15,17-18,21,24-39H2,1-5H3/b10-8-,16-14-,20-19-,23-22-/t40-/m1/s1
InChI KeyZSYMQFVRTIVMFA-JAHIUHDMSA-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 Descriptors
Ontology
StatusDetected and 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
logP5.32ALOGPS
logP7.56ChemAxon
logS-7.4ALOGPS
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 Count38ChemAxon
Refractivity229.53 m³·mol⁻¹ChemAxon
Polarizability90 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, Positivesplash10-000i-9181141300-122966da1187e9f13469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4491020100-868c384e7b84e81230adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q0-9364020000-8b4b6da7d56c6c0a3b5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0095001400-a23fbc877e3fc85c30a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098002000-0cd42575640e807a89ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-5193100000-113df020108793c2fa5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-5b7a290fc7c8d4534f13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0085043900-3a58a596fc3cfeafedd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-8396500000-2b870ae82e66245047dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-fb17bd89e0dbf4476c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-d42a6dc7b67679b57a97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fir-0101490300-6b9d45f785fcfcbac104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-b98e9d2d756a1104b321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-d92091f9cf400c110537Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-f0a2e10786ef89689e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-fd248ad900d1f4236853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000900-5dd296d2b9d56fc4c0f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uii-0099000900-def7911c65c8a1611846Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-117f3fc6982fc425d794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000900-e0182f758af441932884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0008-0600490200-9ff7dff4fe3789e17d14Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified0.009 +/- 0.003 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected and Quantified0.3 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.3 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.18 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.32 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0008459
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 ID88897
PubChem Compound ID53479057
Kegg Compound IDNot Available
YMDB IDYMDB02132
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available