PC(o-20:0/18:3(9Z,12Z,15Z)) (CHEM041236)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:17:25 UTC
Update Date2016-11-09 01:22:26 UTC
Accession NumberCHEM041236
Identification
Common NamePC(o-20:0/18:3(9Z,12Z,15Z))
ClassSmall Molecule
DescriptionPC(O-20:0/18:3(9Z,12Z,15Z)), also known as phosphatidylcholine(20:0/18:3) or gpcho(20:0/18:3), 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. Thus, PC(O-20:0/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-20:0/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidyl-2-a-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Arachidyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(20:0/18:3)HMDB
Gpcho(20:0/18:3n3)HMDB
Gpcho(20:0/18:3W3)HMDB
Gpcho(38:3)HMDB
LecithinHMDB
PC Ae C38:3HMDB
PC(20:0/18:3)HMDB
PC(20:0/18:3n3)HMDB
PC(20:0/18:3W3)HMDB
PC(38:3)HMDB
PC(O-38:3)HMDB
Phosphatidylcholine(20:0/18:3)HMDB
Phosphatidylcholine(20:0/18:3n3)HMDB
Phosphatidylcholine(20:0/18:3W3)HMDB
Phosphatidylcholine(38:3)HMDB
1-Eicosanyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-20:0/18:3(9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC46H88NO7P
Average Molecular Mass798.167 g/mol
Monoisotopic Mass797.630 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
SMILESCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI IdentifierInChI=1S/C46H88NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-26-28-30-32-34-36-38-41-51-43-45(44-53-55(49,50)52-42-40-47(3,4)5)54-46(48)39-37-35-33-31-29-27-25-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,25,45H,6-8,10,12-14,16,18-20,22-24,26-44H2,1-5H3/b11-9-,17-15-,25-21-/t45-/m1/s1
InChI KeyAPWUUZRAVVATRC-GBRUYZQDSA-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
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 Solubility2.4e-05 g/LALOGPS
logP6.42ALOGPS
logP10.08ChemAxon
logS-7.6ALOGPS
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 Count43ChemAxon
Refractivity247.07 m³·mol⁻¹ChemAxon
Polarizability100.32 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, Positivesplash10-000i-9161032400-1b2569324de032e5a481Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-4292011100-4740f5173d2b51a4e850Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-8095003100-4bf89c39d5a8bfce1e2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0080000900-aeafab806820f908355cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-1090202400-faae1fb01e108325e062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090100000-9db6d029afea25b4f35dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-e880c2b27fa01dea7aebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0040001900-0dd08a94717ba758ae90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090200000-59c41facdf2ce5c005aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-3bbd72b5162d82d6f10cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000090-3bbd72b5162d82d6f10cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-0060120910-f788e189dffdf2635527Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-2639f7db82cbebc00840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-2639f7db82cbebc00840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001s-1900061700-1333bc4aa195ef81d42bSpectrum
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 IDHMDB0013440
FooDB IDFDB029440
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID89852
PubChem Compound ID52923836
Kegg Compound IDNot Available
YMDB IDNot Available
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)
2. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Phospholipids Handbook
8. The lipid handbook with CD-ROM