Showing metabocard for PC(o-20:0/22:0) (LMDB00612)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:44 UTC
Update Date2016-07-19 23:08:20 UTC
LmdbLMDB00612
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-20:0/22:0)
DescriptionPC(o-20:0/22:0) 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-20:0/22:0), in particular, consists of one chain of Arachidyl alcohol at the C-1 position and one chain of behenic acid at the C-2 position. The Arachidyl alcohol moiety is derived from corn oil, while the behenic acid moiety is derived from groundnut oil. 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-Arachidyl-2-behenoyl-sn-glycero-3-phosphocholineChEBI
Phosphatidylcholine(20:0/22:0)Lipid Annotator, HMDB
GPCho(42:0)Lipid Annotator, HMDB
GPCho(20:0/22:0)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(42:0)Lipid Annotator, HMDB
PC(42:0)Lipid Annotator, HMDB
PC(o-20:0/22:0)Lipid Annotator
1-eicosanyl-2-docosanoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(20:0/22:0)Lipid Annotator, HMDB
PC Ae C42:0HMDB
PC(O-42:0)HMDB
Chemical FormulaC50H102NO7P
Average Molecular Weight860.3211
Monoisotopic Molecular Weight859.739391135
IUPAC Name(2-{[(2R)-2-(docosanoyloxy)-3-(icosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(docosanoyloxy)-3-(icosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C50H102NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-27-29-31-33-35-37-39-41-43-50(52)58-49(48-57-59(53,54)56-46-44-51(3,4)5)47-55-45-42-40-38-36-34-32-30-28-25-23-21-19-17-15-13-11-9-7-2/h49H,6-48H2,1-5H3/t49-/m1/s1
InChI KeyBJUWREINODTBMO-ANFMRNGASA-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
logP6.9ALOGPS
logP12.94ChemAxon
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 Count50ChemAxon
Refractivity262.12 m³·mol⁻¹ChemAxon
Polarizability112.55 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, Positivesplash10-0079-9116032130-204506cfe86b1373615fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008i-6369031100-a3521964bfa727a24b16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-9048004300-3415ad89e17df784d5a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0027000390-9169a75fbbccbdc08f93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ads-2076200920-2a9e8e0d3e08fddeaf28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bj-7079300000-70f8b824f31668106c21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-9e95a190798e57dd3197Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000090-9e95a190798e57dd3197Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1900061070-5219789a31a898d7b2eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-cf06f03957c29f24974aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0003001390-48bc13b9125463a73698Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3009200000-9fc6d61b76c1e3940171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-3c9cd775dbc40c83e334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000000090-3c9cd775dbc40c83e334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-0006120190-ef40abdb460485f523a8Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected and Quantified0.3899 +/- 0.0266-0.3521+/-0.0266 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.4187 +/- 0.0288-0.3121+/-0.0288 uMNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0013443
FooDB IDFDB029443
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24822916
ChEBI ID86253
PubChem Compound ID24779354
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available