Record Information
Version1.0
Creation date2011-09-21 01:55:58 UTC
Update date2019-11-27 17:44:26 UTC
Primary IDFDB029446
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(o-22:0/18:3(9Z,12Z,15Z))
DescriptionPC(o-22:0/18:3(9Z,12Z,15Z)) 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(o-22:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of Behenyl alcohol at the C-1 position and one chain of a-linolenic acid at the C-2 position. The Behenyl alcohol moiety is derived from Rice bran, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Behenyl-2-a-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Behenyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:0/18:3)HMDB
Gpcho(22:0/18:3n3)HMDB
Gpcho(22:0/18:3W3)HMDB
Gpcho(40:3)HMDB
LecithinHMDB
PC Ae C40:3HMDB
PC(22:0/18:3)HMDB
PC(22:0/18:3n3)HMDB
PC(22:0/18:3W3)HMDB
PC(40:3)HMDB
PC(O-40:3)HMDB
Phosphatidylcholine(22:0/18:3)HMDB
Phosphatidylcholine(22:0/18:3n3)HMDB
Phosphatidylcholine(22:0/18:3W3)HMDB
Phosphatidylcholine(40:3)HMDB
1-Docosanyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholineHMDB
PC(o-22:0/18:3(9Z,12Z,15Z))Lipid Annotator
1-Behenyl-2-a-linolenoyl-sn-glycero-3-ocholineHMDB
1-Behenyl-2-alpha-linolenoyl-sn-glycero-3-ocholineHMDB
Predicted Properties
PropertyValueSource
Water Solubility2.5e-05 g/LALOGPS
logP6.71ALOGPS
logP10.97ChemAxon
logS-7.5ALOGPS
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 Count45ChemAxon
Refractivity256.27 m³·mol⁻¹ChemAxon
Polarizability104.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H92NO7P
IUPAC name(2-{[(2R)-3-(docosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C48H92NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-28-30-32-34-36-38-40-43-53-45-47(46-55-57(51,52)54-44-42-49(3,4)5)56-48(50)41-39-37-35-33-31-29-27-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,27,47H,6-8,10,12-14,16,18-20,22-26,28-46H2,1-5H3/b11-9-,17-15-,27-21-/t47-/m1/s1
InChI KeyCPEAXNSICHTTDR-BKMBJBKQSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
Average Molecular Weight826.2203
Monoisotopic Molecular Weight825.661140815
Classification
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
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-9152032130-df4444cd642e27437597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0913-6398022210-fd17b5968acff7d979b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-9067002200-3d2ca3e75349c5bd90e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0082000390-76a696d5cac59a2c9512View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2085200920-313d9c8609c6b4a73d5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5092200000-c81ededefaa94295aeffView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481747
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13446
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phospholipase D2PLD2O14939
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Lecithin retinol acyltransferaseLRATO95237
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference