Showing metabocard for PC(18:0/20:4(5Z,8Z,11Z,14Z)) (LMDB00498)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:12 UTC
Update Date2016-07-20 21:01:40 UTC
LmdbLMDB00498
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(18:0/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(18:0/20:4(5Z,8Z,11Z,14Z)) 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(18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the arachidonic acid moiety is derived from animal fats and eggs. 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
(2R)-2-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-C18:0-2-C20:4(Omega-6)-phosphatidylcholineChEBI
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-2-arachidonoyl-GPCChEBI
1-Stearoyl-2-arachidonoyl-GPC (18:0/20:4)ChEBI
1-Stearoyl-2-arachidonoylphosphatidylcholineChEBI
GPC(18:0/20:4)ChEBI
PC(18:0/20:4)ChEBI
PC(18:0/20:4n6)ChEBI
PC(18:0/20:4omega6)ChEBI
PC(18:0/20:4W6)ChEBI
PC(38:4)ChEBI
Phosphatidylcholine(18:0/20:4)ChEBI
Phosphatidylcholine(18:0/20:4n6)ChEBI
Phosphatidylcholine(18:0/20:4omega6)ChEBI
Phosphatidylcholine(18:0/20:4W6)ChEBI
Phosphatidylcholine(38:4)ChEBI
(2R)-2-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyloxy]-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineHMDB
GPCho(18:0/20:4)HMDB
GPCho(38:4)HMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
1-Octadecanoyl-2-arachidonyl-sn-glycero-3-phosphocholineHMDB
1-Stearoyl-2-arachidonoyl phosphatidylcholineHMDB
1-Stearoyl-2-arachidonoyl-3-phosphorylcholineHMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholineHMDB
1-Stearoyl-2-arachidonoyl-sn-glycero-phosphatidylcholineHMDB
1-Stearoyl-2-archidonyl-3-sn-phosphatidylcholineHMDB
18:0/20:4 phosphatidylcholineHMDB
GPC(18:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPC(18:0/20:4n6)HMDB
GPC(18:0/20:4W6)HMDB
GPC(38:4)HMDB
GPCho(18:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPCho(18:0/20:4n6)HMDB
GPCho(18:0/20:4W6)HMDB
Phosphatidylcholine(18:0/20:4(5Z,8Z,11Z,14Z))HMDB
PC(18:0/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC46H84NO8P
Average Molecular Weight810.1348
Monoisotopic Molecular Weight809.593455181
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,44H,6-13,15,17-19,21,23-24,26,28-30,32,34-43H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t44-/m1/s1
InChI KeyPSVRFUPOQYJOOZ-QNPWAGBNSA-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 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
logP6.07ALOGPS
logP9.33ChemAxon
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 Count42ChemAxon
Refractivity247.94 m³·mol⁻¹ChemAxon
Polarizability98.69 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-0000000090-192ed45188cac140e1edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-027d9ab618ed6e32122cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1900041210-94ec561a3288cc08361bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-bd4db731926b5d2cbe56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000190-c053420ce1420abe1479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-9ce17a305cd08da2878dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-20235538cb799e7cb64eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-58feaf75d511d75d6599Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uf6-0099000090-7f1ec3fec9e8c6930b32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-12f7c14a559d8169eb4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000090-4e1c9c4510d5cf1106a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-fe32dc17f26ba414e09eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-fa334b794ce842b59d7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0074004390-c2dd779ebfe244586a1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-5192000000-95fabc301687f9015dcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000090-b25dca7fc1b5373b3809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000190-58e0c5d29433cc0e7cdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0200498220-9ec01b331a44705e5c2cSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0008048
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 ID74965
PubChem Compound ID16219824
Kegg Compound IDNot Available
YMDB IDYMDB01897
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available