1-18:3-2-18:2-phosphatidylcholine (CHEM041833)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:42:59 UTC
Update Date2016-11-09 01:22:33 UTC
Accession NumberCHEM041833
Identification
Common Name1-18:3-2-18:2-phosphatidylcholine
ClassSmall Molecule
DescriptionPC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)), also known as gpcho(18:3/18:2) or gpcho(36:5), 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(9Z,12Z,15Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-a-linolenoyl-2-linoleoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(18:3/18:2)Lipid Annotator, HMDB
GPCho(36:5)Lipid Annotator, HMDB
PC(18:3/18:2)Lipid Annotator, HMDB
Phosphatidylcholine(36:5)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(36:5)Lipid Annotator, HMDB
Phosphatidylcholine(18:3/18:2)Lipid Annotator, HMDB
1-(9Z,12Z,15Z-octadeatrienoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC44H78NO8P
Average Molecular Mass780.066 g/mol
Monoisotopic Mass779.547 g/mol
CAS Registry NumberNot Available
IUPAC Nametrimethyl(2-{[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
SMILESCCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C44H78NO8P/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/h8,10,14-17,20-23,42H,6-7,9,11-13,18-19,24-41H2,1-5H3/b10-8-,16-14-,17-15-,22-20-,23-21-/t42-/m1/s1
InChI KeyQFDYIDGUKXRPKH-VSLGLSMXSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.1e-05 g/LALOGPS
logP5.53ALOGPS
logP8.08ChemAxon
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 Count39ChemAxon
Refractivity239.85 m³·mol⁻¹ChemAxon
Polarizability92.68 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gx9-9061061400-0eccc65da0f1eb81d419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5293041100-556cd2052dc601ba2406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9066040100-91f2a6491a7bfc420094Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090002800-fef2269c143529d4c0a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090104200-5a0d44619d5562f8e125Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3090100000-4a1f2acb05a69649bfe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-d1fecbe733b4fab2e6fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000090-d2e447c62bdff081e2d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0090000040-a30e930ed397dcfebca4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-6ac0ce44c5d362b404abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0071030900-c264d4e92b83ab02a6f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3190300000-aba59906d7f85ced85a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-be732a4aa7f691f68131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-37d5d9b145362a874a18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900369110-afe8bff0cd7fe8179ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-11abb7219d74a5a60a04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-8b887b2cddb30aa5f84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900050300-d7be45ffcd3d54601b68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-82395bc23558c5e73383Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-d73ebce581a3424e67e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi1-0200498400-fb911a077623a696d58fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0008204
FooDB IDFDB030237
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766866
ChEBI IDNot Available
PubChem Compound ID52922845
Kegg Compound IDNot Available
YMDB IDYMDB02005
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)