| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 19:49:47 -0600 |
| Update Date |
2013-02-08 17:21:33 -0700 |
| HMDB ID |
HMDB09195 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) |
| Description |
PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines 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. PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)), in particular, consists of two chains of stearidonic acid at the C-1 and C-2 positions. The stearidonic acid moieties are derived from seed oils. 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. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1,2-Distearidonoyl-rac-glycero-3-phosphoethanolamine
- GPEtn(18:4/18:4)
- GPEtn(18:4n3/18:4n3)
- GPEtn(18:4w3/18:4w3)
- GPEtn(36:8)
- PE(18:4/18:4)
- PE(18:4n3/18:4n3)
- PE(18:4w3/18:4w3)
- PE(36:8)
- Phophatidylethanolamine(18:4/18:4)
- Phophatidylethanolamine(18:4n3/18:4n3)
- Phophatidylethanolamine(18:4w3/18:4w3)
- Phophatidylethanolamine(36:8)
|
| Chemical Formula |
C41H66NO8P |
| Average Molecular Weight |
731.9384 |
| Monoisotopic Molecular Weight |
731.452604605 |
| IUPAC Name |
(2-aminoethoxy)[(2R)-2,3-bis[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxy]phosphinic acid |
| Traditional IUPAC Name |
2-aminoethoxy(2R)-2,3-bis[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxyphosphinic acid |
| CAS Registry Number |
Not Available |
| SMILES |
[H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC |
| InChI Identifier |
InChI=1S/C41H66NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,39H,3-4,9-10,15-16,21-22,27-38,42H2,1-2H3,(H,45,46)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-/t39-/m1/s1 |
| InChI Key |
XPVPRBUMVPRRIJ-FWANEPEWSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphoethanolamines |
| Other Descriptors |
- Aliphatic Acyclic Compounds
|
| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Organic Hypophosphite
- Organic Phosphite
- Phosphoethanolamine
- Phosphoric Acid Ester
- Primary Aliphatic Amine (Alkylamine)
|
| Direct Parent |
Phosphatidylethanolamines |
| Ontology |
|---|
| Status |
Expected and Not 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 |
Not Available
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
Predicted Concentrations
|
|---|
|
| Blood |
0.000009930 +/- 0.000008860 uM |
Adult (>18 years old) |
Both |
Normal (Most Probable) |
Calculated using MetaboAnalyst
|
| Blood |
0.033333333 +/- 0.028867513 uM |
Adult (>18 years old) |
Both |
Normal (Upper Limit) |
Calculated using MetaboAnalyst
|
|
| 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 |
FDB026385 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24768657  |
| KEGG Compound ID |
C00350 |
| BioCyc ID |
L-1-PHOSPHATIDYL-ETHANOLAMINE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB09195 |
| Metagene Link |
HMDB09195 |
| METLIN ID |
Not Available |
| PubChem Compound |
52924455 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
