Showing metabocard for PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (LMDB00504)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:20 UTC
Update Date2021-04-30 20:57:46 UTC
LmdbLMDB00504
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(18:2(9Z,12Z)/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(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, 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
1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Linoleoyl-2-arachidonoyl-GPCChEBI
1-Linoleoyl-2-arachidonoyl-GPC (18:2/20:4n6)ChEBI
GPC(18:2/20:4n6)ChEBI
GPCho(18:2/20:4)ChEBI
GPCho(18:2n6/20:4n6)ChEBI
GPCho(18:2W6/20:4W6)ChEBI
PC(18:2/20:4)ChEBI
PC(18:2n6/20:4n6)ChEBI
PC(18:2W6/20:4W6)ChEBI
Phosphatidylcholine(18:2/20:4)ChEBI
Phosphatidylcholine(18:2n6/20:4n6)ChEBI
Phosphatidylcholine(18:2W6/20:4W6)ChEBI
1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(38:6)HMDB
LecithinHMDB
GPCho(38:6)HMDB
PC(38:6)HMDB
PC Aa C38:6HMDB
1-Linoleoyl-2-arachidonoyl-sn-glycero-phosphatidylcholineHMDB
GPC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))HMDB
GPC(18:2/20:4)HMDB
GPC(18:2n6/20:4n6)HMDB
GPC(18:2W6/20:4W6)HMDB
GPC(38:6)HMDB
GPCho(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))HMDB
Phosphatidylcholine(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))HMDB
PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC46H80NO8P
Average Molecular Weight806.1031
Monoisotopic Molecular Weight805.562155053
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=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/C46H80NO8P/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/h14-17,20-22,24-25,27,31,33,44H,6-13,18-19,23,26,28-30,32,34-43H2,1-5H3/b16-14-,17-15-,22-20-,24-21-,27-25-,33-31-/t44-/m1/s1
InChI KeyZZSZQATYGVHNLZ-PUMLCSCDSA-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
logP5.73ALOGPS
logP8.61ChemAxon
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 Count40ChemAxon
Refractivity250.17 m³·mol⁻¹ChemAxon
Polarizability95.63 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, Positivesplash10-0a4i-0000000090-ca3483f6dd540baaf891Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-0f04b1deeba14a94356fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041210-7535b3c0ca52eb410d47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-1e78e28c2730b5262b1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-f42482894aa2a9df4b6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0200498220-882e69f0546935966511Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-16b357af2387839179b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-3c2d12da68314bd9861cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ui6-0099000090-659059b54ab6c0df71cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-8b00eebc929d9a9097dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-71d714a518c51ee5a089Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-b70a47abc65e2e98867cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6dad79f01b1173c5421fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0064004390-a2e07e22be3f1a2bfb6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5191000000-50eb4d0b8a691e3a81efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-489803391fb15e1d23f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-e0c7549473f8627cae46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900041210-6a88b3160e1dd26f3b53Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Bile acid
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Bile acidDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified7.8418 +/- 2.3016 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.2744 +/- 2.3208 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified9.5418 +/- 2.8228 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified7.5842 +/- 3.4934 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.3775 +/- 2.5698 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.6223 +/- 3.2163 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified6.3918 +/- 1.8193 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.3557 +/- 2.3314 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified9.2211 +/- 5.335 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified7.1484 +/- 2.5622 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified4.39 +/- 2.12 uMNot AvailableOvine
    • Candidate serum m...
 details
SerumDetected and Quantified7.6936 +/- 3.5597 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.3885 +/- 3.2165 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
DrugBank IDNot Available
HMDB IDHMDB0008147
FooDB IDFDB025337
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766809
ChEBI ID84563
PubChem Compound ID24778979
Kegg Compound IDNot Available
YMDB IDYMDB01969
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available