Showing metabocard for PC(o-22:0/20:1(11Z)) (LMDB00615)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:48 UTC
Update Date2016-07-19 23:33:19 UTC
LmdbLMDB00615
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-22:0/20:1(11Z))
DescriptionPC(o-22:0/20:1(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(o-22:0/20:1(11Z)), in particular, consists of one chain of Behenyl alcohol at the C-1 position and one chain of eicosenoic acid at the C-2 position. The Behenyl alcohol moiety is derived from Rice bran, while the eicosenoic acid moiety is derived from vegetable oils and cod 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-Behenyl-2-eicosenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:0/20:1)HMDB
Gpcho(22:0/20:1n9)HMDB
Gpcho(22:0/20:1W9)HMDB
Gpcho(42:1)HMDB
LecithinHMDB
PC Ae C42:1HMDB
PC(22:0/20:1)HMDB
PC(22:0/20:1n9)HMDB
PC(22:0/20:1W9)HMDB
PC(42:1)HMDB
PC(O-42:1)HMDB
Phosphatidylcholine(22:0/20:1)HMDB
Phosphatidylcholine(22:0/20:1n9)HMDB
Phosphatidylcholine(22:0/20:1W9)HMDB
Phosphatidylcholine(42:1)HMDB
1-Docosanyl-2-(11-eicosenoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-22:0/20:1(11Z))Lipid Annotator
Chemical FormulaC50H100NO7P
Average Molecular Weight858.3053
Monoisotopic Molecular Weight857.723741071
IUPAC Name(2-{[(2R)-3-(docosyloxy)-2-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(docosyloxy)-2-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C50H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-28-30-32-34-36-38-40-42-45-55-47-49(48-57-59(53,54)56-46-44-51(3,4)5)58-50(52)43-41-39-37-35-33-31-29-27-23-21-19-17-15-13-11-9-7-2/h21,23,49H,6-20,22,24-48H2,1-5H3/b23-21-/t49-/m1/s1
InChI KeyXKPLZICHJPNOFR-WIEGMJJDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • 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
logP6.93ALOGPS
logP12.58ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count49ChemAxon
Refractivity263.24 m³·mol⁻¹ChemAxon
Polarizability111.37 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, Negativesplash10-0006-0000000090-656bc5fb5ee8977d19e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000000090-656bc5fb5ee8977d19e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0006120190-fecfe15aec927569ef78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-0d9c4fe61ea03c749608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000090-0d9c4fe61ea03c749608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-1900061160-6d0664d7d471183576adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-9e6b8f53a60370b7a9f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0051001390-bbda392ad04c0813dc84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4019400000-7a510af11edac9168d4bSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified0.017 +/- 0.002 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected and Quantified0.15 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.16 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.13 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.19 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013447
FooDB IDFDB029447
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 ID53481749
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available