Showing metabocard for PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (LMDB00499)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:13 UTC
Update Date2021-04-30 20:57:49 UTC
LmdbLMDB00499
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosahexaenoic acid moiety is derived from fish oils. 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-Stearoyl-2-docosahexaenoyl-GPCChEBI
1-Stearoyl-2-docosahexaenoyl-GPC (18:0/22:6)ChEBI
1-Stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholineChEBI
GPC(18:0/22:6)ChEBI
GPCho(18:0/22:6)ChEBI
GPCho(18:0/22:6n3)ChEBI
GPCho(18:0/22:6W3)ChEBI
PC(18:0/22:6)ChEBI
PC(18:0/22:6n3)ChEBI
Phosphatidylcholine(18:0/22:6)ChEBI
Phosphatidylcholine(18:0/22:6n3)ChEBI
Phosphatidylcholine(18:0/22:6W3)ChEBI
PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
GPCho(40:6)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(40:6)Lipid Annotator, HMDB
PC(40:6)Lipid Annotator, HMDB
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
1-SDGP CPDMeSH, HMDB
Chemical FormulaC48H84NO8P
Average Molecular Weight834.1562
Monoisotopic Molecular Weight833.593455181
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C48H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,29,31,35,37,46H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-34,36,38-45H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-,37-35-/t46-/m1/s1
InChI KeyFAUYAENFVCNTAL-PFFNLMTBSA-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
logP6.21ALOGPS
logP9.5ChemAxon
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
Refractivity259.37 m³·mol⁻¹ChemAxon
Polarizability99.54 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, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-a40775102b4d4f815a48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-d8c58c6fa3297db5857eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041120-721fc981a3b2eb2de080Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-984ea4236848a8ef68fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0054004390-97dd5572238142670832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3092000000-a27a95080a96f99a900aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-002c799c60fc4d73f51dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000090-95996a0eceb154950c1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0099000090-16f8aee1b2f1f1764802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-34edac6f4ace79854defSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-1e3aed1deea007ebddb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041120-e55f8251a338f6ee78eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-25d8a8b10dfd14fc7816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-70c32db1d1532dee3550Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0900179110-38584900c0b472da0b79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000090-69be100d9c131d43eb56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000190-4beaa04d4cbeaad3182cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200498220-374f7165d7cf8482e296Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified11.7906 +/- 5.6684 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified11.5759 +/- 5.2611 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified6.63 +/- 3.23 uMNot AvailableOvine
    • Candidate serum m...
 details
SerumDetected and Quantified10.868 +/- 4.0812 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified12.9962 +/- 4.3543 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified14.3261 +/- 5.3209 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified12.159 +/- 6.1592 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified12.416 +/- 5.1008 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified14.9724 +/- 6.4534 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified8.7993 +/- 3.1967 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified12.9395 +/- 4.9916 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified13.7334 +/- 7.9095 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected and Quantified10.1181 +/- 4.2773 uM
Normal		Ovine
    • Goldansaz et al.,...
 details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0008057
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 ID24766721
ChEBI ID84829
PubChem Compound ID24778876
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available