Showing metabocard for PC(o-18:0/20:0) (LMDB00597)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:23 UTC
Update Date2016-07-20 20:46:04 UTC
LmdbLMDB00597
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-18:0/20:0)
DescriptionPC(o-18:0/20:0) 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-18:0/20:0), in particular, consists of one chain of Stearyl alcohol at the C-1 position and one chain of arachidic acid at the C-2 position. The Stearyl alcohol moiety is derived from beef fat, fish oil, while the arachidic acid moiety is derived from peanut 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-Octadecyl-2-eicosanoyl-sn-glycero-3-phosphocholineChEBI
1-Stearyl-2-arachidoyl-sn-glycero-3-phosphocholineChEBI
GPCho O-18:0/20:0ChEBI
GPCho(O-18:0/20:0)ChEBI
PC O-18:0/20:0ChEBI
Phosphatidylcholine(O-18:0/20:0)ChEBI
1-Stearyl-2-arachidonyl-sn-glycero-3-phosphocholineHMDB
Gpcho(18:0/20:0)HMDB
Gpcho(38:0)HMDB
LecithinHMDB
PC Ae C38:0HMDB
PC(18:0/20:0)HMDB
PC(38:0)HMDB
PC(O-38:0)HMDB
Phosphatidylcholine(18:0/20:0)HMDB
Phosphatidylcholine(38:0)HMDB
1-Octadecanyl-2-eicosanoyl-sn-glycero-3-phosphocholineHMDB
PC(o-18:0/20:0)Lipid Annotator
Chemical FormulaC46H94NO7P
Average Molecular Weight804.2148
Monoisotopic Molecular Weight803.676790879
IUPAC Name(2-{[(2R)-2-(icosanoyloxy)-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(icosanoyloxy)-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C46H94NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h45H,6-44H2,1-5H3/t45-/m1/s1
InChI KeyBVCZSMAYNCVQDT-WBVITSLISA-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
logP6.47ALOGPS
logP11.16ChemAxon
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 Count46ChemAxon
Refractivity243.72 m³·mol⁻¹ChemAxon
Polarizability104.47 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, Positivesplash10-0f79-9152212130-18b694ff72196dedd9f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2j-5293011200-f44acea79241c8ba59feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-9085004200-f2bda74a7be0fe21584dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-0045001190-d20e77e0ee78cf1804e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-2093203420-f1327e98bbd4a6d938dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02bf-5094200000-b36f77363836d8eead18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-c7590354f89a4640c45aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0021001390-a43aeef5bc579834dbabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-4029201000-7f5eed55d0fde17b8f7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-e90bb2ed62a6f09effdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000090-e90bb2ed62a6f09effdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900141160-7699ba8c98b3d367f7e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-7a733192d1b6cff2fdb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000090-7a733192d1b6cff2fdb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0006300910-f535fd5c0712e038ba7eSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected and Quantified0.65 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.68 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.64 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.89 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
DrugBank IDNot Available
HMDB IDHMDB0013419
FooDB IDFDB029419
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24822893
ChEBI ID74482
PubChem Compound ID24779329
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available