Showing metabocard for PC(18:0/18:3(6Z,9Z,12Z)) (LMDB00496)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:51:09 UTC
Update Date2016-07-20 21:01:39 UTC
LmdbLMDB00496
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(18:0/18:3(6Z,9Z,12Z))
DescriptionPC(18:0/18:3(6Z,9Z,12Z)) 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(18:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the g-linolenic acid moiety is derived from animal fats. 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-Stearoyl-2-g-linolenoyl-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholineChEBI
GPCho(18:0/18:3)ChEBI
GPCho(18:0/18:3n6)ChEBI
GPCho(18:0/18:3W6)ChEBI
PC(18:0/18:3)ChEBI
PC(18:0/18:3n6)ChEBI
PC(18:0/18:3W6)ChEBI
Phosphatidylcholine(18:0/18:3)ChEBI
Phosphatidylcholine(18:0/18:3n6)ChEBI
Phosphatidylcholine(18:0/18:3W6)ChEBI
1-Stearoyl-2-γ-linolenoyl-sn-glycero-3-phosphocholineGenerator
GPCho(36:3)Lipid Annotator, HMDB
PC(36:3)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(36:3)Lipid Annotator, HMDB
PC(18:0/18:3(6Z,9Z,12Z))Lipid Annotator
1-octadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Chemical FormulaC44H82NO8P
Average Molecular Weight784.0975
Monoisotopic Molecular Weight783.577805117
IUPAC Nametrimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H82NO8P/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/h15,17,21,23,27,29,42H,6-14,16,18-20,22,24-26,28,30-41H2,1-5H3/b17-15-,23-21-,29-27-/t42-/m1/s1
InChI KeyKJVJKBRMUDGTKA-NZXQIXPOSA-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
logP5.79ALOGPS
logP8.81ChemAxon
logS-7.5ALOGPS
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 Count41ChemAxon
Refractivity237.62 m³·mol⁻¹ChemAxon
Polarizability95 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-9081052400-cbc1cf6b4a37d1de9214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u9-4292021100-7ad04a2c895103b74843Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8095020100-960b863245c4e225be89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000300-1a468679a6149dbc6b3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0090001000-5393c0a85c1250350a89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pr-3090100000-426f104bf5b1d72503ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-f44acebd42271f9d37feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-d39b20e156e47b15fe77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200498400-f75dff37980d754872c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-02472e506be910245a7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000090-4a8a30d711ba5dbcbc6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0090000040-d4a837443937b0025ddeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-016fbc06bd6c36a12e4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-7ba4362bb833d26b28b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041300-914319d13a6e3e697365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-f313232611c4c0c71d38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090020700-793d4965b69e11e425b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4190000000-1f42c3349b3c512805aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-1db30625399fdea6b457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-671ed31d83ec847480a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0900369110-2786bfbce693bc75f64fSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Bile acid
  • Liver
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Bile acidDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0008040
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 ID24766705
ChEBI ID86117
PubChem Compound ID52922655
Kegg Compound IDNot Available
YMDB IDYMDB01892
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available