Showing metabocard for PC(18:2(9Z,12Z)/18:0) (LMDB00503)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:18 UTC
Update Date2016-07-20 21:01:41 UTC
LmdbLMDB00503
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(18:2(9Z,12Z)/18:0)
DescriptionPC(18:2(9Z,12Z)/18:0) 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(18:2(9Z,12Z)/18:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame 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-Linoleoyl-2-stearoyl-sn-glycero-3-phosphocholineChEBI
GPCho(18:2/18:0)ChEBI
GPCho(18:2n6/18:0)ChEBI
GPCho(18:2W6/18:0)ChEBI
PC(18:2/18:0)ChEBI
PC(18:2n6/18:0)ChEBI
PC(18:2W6/18:0)ChEBI
Phosphatidylcholine(18:2/18:0)ChEBI
Phosphatidylcholine(18:2n6/18:0)ChEBI
Phosphatidylcholine(18:2W6/18:0)ChEBI
PC(36:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(36:2)Lipid Annotator, HMDB
PC(18:2(9Z,12Z)/18:0)Lipid Annotator
1-(9Z,12Z-octadecadienoyl)-2-octadecanoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(36:2)Lipid Annotator, HMDB
Chemical FormulaC44H84NO8P
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
IUPAC Nametrimethyl(2-{[(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14,16,20,22,42H,6-13,15,17-19,21,23-41H2,1-5H3/b16-14-,22-20-/t42-/m1/s1
InChI KeyDZPKSVTWWIZUMS-FPUNCOTOSA-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 but not 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
logP5.8ALOGPS
logP9.17ChemAxon
logS-7.6ALOGPS
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
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability95.83 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, Negativesplash10-001i-0090001800-b3a1972611ea3769fa43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-1090103300-a72fcd04de0cb44cf0a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pi-3090100000-b54c6a4dd6b6fcfff840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-23df8d3c4971511f3b91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0081030900-336842a235f9ccd697d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4090300000-0657ea1e487e8af6e0c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-683d2aaf9f12a9d08614Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0030000090-ceb91fadb205f9c1b737Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ji-0090000040-f6fcdf71c4ae55cc490bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9061052400-679dfe0e14e38cdf9f16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-5293022100-3c936433f50aedc64014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9075021100-adfb6088014ebf04dee3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-53a8e01f33b2af13f226Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-64f46bdfe255d6a5b5e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0900369110-8282d7071a7afc84c25dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-64c382f846ba04194d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6c06686879d9f7790e62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200498400-bfcef54bcce75991df2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-e54f4b7d729e27672b37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-3a2440aaca7e87ec13a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900041300-d3ccf7461dac2d683004Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0008135
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 ID24766798
ChEBI ID86112
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDYMDB01958
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available