Showing metabocard for PC(o-22:0/22:3(10Z,13Z,16Z)) (LMDB00617)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:51 UTC
Update Date2016-07-19 23:33:28 UTC
LmdbLMDB00617
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-22:0/22:3(10Z,13Z,16Z))
DescriptionPC(o-22:0/22:3(10Z,13Z,16Z)) 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-22:0/22:3(10Z,13Z,16Z)), in particular, consists of one chain of Behenyl alcohol at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The Behenyl alcohol moiety is derived from Rice bran, while the (10Z,13Z,16Z-docosatrienoyl) 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
GPCho(44:3)Lipid Annotator, HMDB
Phosphatidylcholine(44:3)Lipid Annotator, HMDB
PC(22:0/22:3)Lipid Annotator, HMDB
GPCho(22:0/22:3)Lipid Annotator, HMDB
PC(o-22:0/22:3(10Z,13Z,16Z))Lipid Annotator
1-Behenyl-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(44:3)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
1-docosanyl-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(22:0/22:3)Lipid Annotator, HMDB
gpcho(22:0/22:3n6)HMDB
gpcho(22:0/22:3W6)HMDB
PC Ae C44:3HMDB
PC(22:0/22:3n6)HMDB
PC(22:0/22:3W6)HMDB
PC(O-44:3)HMDB
Phosphatidylcholine(22:0/22:3n6)HMDB
Phosphatidylcholine(22:0/22:3W6)HMDB
Chemical FormulaC52H100NO7P
Average Molecular Weight882.3267
Monoisotopic Molecular Weight881.723741071
IUPAC Name(2-{[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-(docosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-(docosyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C52H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,27,29,51H,6-14,16,18-20,22,24-26,28,30-50H2,1-5H3/b17-15-,23-21-,29-27-/t51-/m1/s1
InChI KeyCQBVYLALIKLMGX-TYGMOWAISA-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
logP7.14ALOGPS
logP12.74ChemAxon
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
Refractivity274.67 m³·mol⁻¹ChemAxon
Polarizability112.71 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, Positivesplash10-00li-9117031130-ef3daa06b9a118f35051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067s-4229021100-9fcbe919e3f1f6d62fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-8039011110-812f6e183140e833262cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0008000290-a56f785a4651f3239bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1019200530-db725e714dfeb6f08532Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4029200000-f0dae503fce99371eeb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-bd09935a9e14a7e78d8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0004001090-29fff67691d686a23d2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4009300000-c236460793a0bf11ba1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-96e9e570336d9ee74713Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-96e9e570336d9ee74713Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900061070-fdd29e9fc6835fa2f62eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000009-ca3f7b3580cfc8035037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000000009-ca3f7b3580cfc8035037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0007120191-4611b7ade8684824e1a2Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified0.035 +/- 0.001 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
SerumDetected and Quantified0.042 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.051 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.041 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.048 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013449
FooDB IDFDB029449
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35032631
ChEBI ID86454
PubChem Compound ID53481753
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available