Showing metabocard for PC(18:3(6Z,9Z,12Z)/18:1(9Z)) (BMDB0008170)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:15:18 UTC
Update Date2020-06-04 19:46:17 UTC
BMDB IDBMDB0008170
Secondary Accession Numbers
  • BMDB08170
Metabolite Identification
Common NamePC(18:3(6Z,9Z,12Z)/18:1(9Z))
DescriptionPC(18:3(6Z,9Z,12Z)/18:1(9Z)), also known as gpcho(18:3/18:1) or phosphatidylcholine(18:3/18:1), 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. Thus, PC(18:3(6Z,9Z,12Z)/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-gamma-Linolenoyl-2-oleoyl-sn-glycero-3-phosphocholineChEBI
GPCho(18:3/18:1)ChEBI
GPCho(18:3n6/18:1n9)ChEBI
GPCho(18:3W6/18:1W9)ChEBI
PC(18:3/18:1)ChEBI
PC(18:3n6/18:1n9)ChEBI
PC(18:3W6/18:1W9)ChEBI
Phosphatidylcholine(18:3/18:1)ChEBI
Phosphatidylcholine(18:3n6/18:1n9)ChEBI
Phosphatidylcholine(18:3W6/18:1W9)ChEBI
1-g-Linolenoyl-2-oleoyl-sn-glycero-3-phosphocholineGenerator
1-Γ-linolenoyl-2-oleoyl-sn-glycero-3-phosphocholineGenerator
GPCho(36:4)HMDB
Phosphatidylcholine(36:4)HMDB
LecithinHMDB
PC(36:4)HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineHMDB
PC(18:3(6Z,9Z,12Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC44H80NO8P
Average Molecular Weight782.0817
Monoisotopic Molecular Weight781.562155053
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C44H80NO8P/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/h14,16,20-23,26,28,42H,6-13,15,17-19,24-25,27,29-41H2,1-5H3/b16-14-,22-20-,23-21-,28-26-/t42-/m1/s1
InChI KeyNKQPOVROGSWLTO-NVPMBMBWSA-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 and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.71ALOGPS
logP8.44ChemAxon
logS-7.4ALOGPS
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 Count40ChemAxon
Refractivity238.74 m³·mol⁻¹ChemAxon
Polarizability93.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsr-9061061400-eaea0491be4f453e4023View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u9-5293041100-427da0e12a32551da2ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9075031100-02f3f6aedc2992ee9ad7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090001800-c7427e8f3ab348d25176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090104200-a92f8c359bca51cb28aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u0-3090100000-e94b821c4fcb6baf2792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-bc2a7ab6e102186d0c94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-1f8c8c5ddd6d8082b38dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0200498400-a8dc71ebc7b92d614bf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-3c72155bce4155773a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-064c081755895a2e4178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dk-0900369110-4a69111426c2037dbd2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-08d6fcb41388b1c681f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000090-8399757791cfdf95c0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0090000040-ea2d30f89ff61b7311bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2534b1e8e0eb889fbec2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0071030900-f3cd4bf8fadf1d1e57a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3190300000-dbec47a354f92984a580View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-440a71e9c384cc6f77ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-9035a7e163ecdf01e45fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900050300-d5c624f49dd16e4de5daView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified1.20 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.63 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.86 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.06 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.164 +/- 0.192 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922783
PDB IDNot Available
ChEBI ID86123
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.