| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2010-03-18 10:07:38 -0600 |
| Update Date |
2013-02-08 17:30:14 -0700 |
| HMDB ID |
HMDB13440 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PC(o-20:0/18:3(9Z,12Z,15Z)) |
| Description |
PC(o-20:0/18:3(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-20:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of Arachidyl alcohol at the C-1 position and one chain of a-linolenic acid at the C-2 position. The Arachidyl alcohol moiety is derived from corn oil, 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Arachidyl-2-a-linolenoyl-sn-glycero-3-phosphocholine
- 1-Arachidyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholine
- GPCho(20:0/18:3)
- GPCho(20:0/18:3n3)
- GPCho(20:0/18:3w3)
- GPCho(38:3)
- Lecithin
- PC ae C38:3
- PC(20:0/18:3)
- PC(20:0/18:3n3)
- PC(20:0/18:3w3)
- PC(38:3)
- PC(O-38:3)
- Phosphatidylcholine(20:0/18:3)
- Phosphatidylcholine(20:0/18:3n3)
- Phosphatidylcholine(20:0/18:3w3)
- Phosphatidylcholine(38:3)
|
| Chemical Formula |
C46H88NO7P |
| Average Molecular Weight |
798.1672 |
| Monoisotopic Molecular Weight |
797.629840687 |
| IUPAC Name |
(2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
| Traditional IUPAC Name |
(2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC |
| InChI Identifier |
InChI=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 Key |
APWUUZRAVVATRC-GBRUYZQDSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphocholines |
| Other Descriptors |
- Aliphatic Acyclic Compounds
|
| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Choline
- Dialkyl Ether
- Fatty Acid Ester
- Organic Hypophosphite
- Organic Phosphite
- Phosphocholine
- Phosphoethanolamine
- Phosphoric Acid Ester
- Quaternary Ammonium Salt
|
| Direct Parent |
Other Glycerophosphocholines |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Urine |
Detected and Quantified |
|
0.002 (0.0012-0.0028) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by DFI-MS/MS (Biocrates kit)
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB029440 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB13440  |
| Metagene Link |
HMDB13440 |
| METLIN ID |
Not Available |
| PubChem Compound |
52923836 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
