| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 19:50:08 -0600 |
| Update Date |
2013-02-08 17:21:36 -0700 |
| HMDB ID |
HMDB09215 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PE(18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)) |
| Description |
PE(18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)) 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)/P-18:1(11Z)), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. 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. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-Stearidonoyl-2-(1-enyl-vaccenoyl)-sn-glycero-3-phosphoethanolamine
- GPEtn(18:4/18:1)
- GPEtn(18:4n3/18:1n7)
- GPEtn(18:4w3/18:1w7)
- GPEtn(36:5)
- PE(18:4/18:1)
- PE(18:4n3/18:1n7)
- PE(18:4w3/18:1w7)
- PE(36:5)
- Phophatidylethanolamine(18:4/18:1)
- Phophatidylethanolamine(18:4n3/18:1n7)
- Phophatidylethanolamine(18:4w3/18:1w7)
- Phophatidylethanolamine(36:5)
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| Chemical Formula |
C41H72NO7P |
| Average Molecular Weight |
721.9866 |
| Monoisotopic Molecular Weight |
721.504640175 |
| IUPAC Name |
(2-aminoethoxy)[(2R)-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxy]phosphinic acid |
| Traditional IUPAC Name |
2-aminoethoxy(2R)-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]-3-[(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)O\C=C/CCCCCCCC\C=C/CCCCCC |
| InChI Identifier |
InChI=1S/C41H72NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-36-46-40(39-49-50(44,45)48-37-35-42)38-47-41(43)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12-15,18,20,24,26,33,36,40H,3-5,7,9-11,16-17,19,21-23,25,27-32,34-35,37-39,42H2,1-2H3,(H,44,45)/b8-6-,14-12-,15-13-,20-18-,26-24-,36-33-/t40-/m1/s1 |
| InChI Key |
ZKHZGLULXDLLMK-KQNMAQKCSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Organophosphorus Compounds |
| Class |
Organic Phosphoric Acids and Derivatives |
| Sub Class |
Organophosphate Esters |
| Other Descriptors |
- Aliphatic Acyclic Compounds
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| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Enol Ether
- Fatty Acid Ester
- Organic Hypophosphite
- Organic Phosphite
- Primary Aliphatic Amine (Alkylamine)
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| Direct Parent |
Phosphoethanolamines |
| Ontology |
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| Status |
Expected and Not Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| 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 |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
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Not Available |
| Abnormal Concentrations |
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Not Available |
| Associated Disorders and Diseases |
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| 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 |
FDB026405 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24768677  |
| KEGG Compound ID |
C00350 |
| BioCyc ID |
L-1-PHOSPHATIDYL-ETHANOLAMINE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB09215 |
| Metagene Link |
HMDB09215 |
| METLIN ID |
Not Available |
| PubChem Compound |
53479707 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available
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| Enzymes |
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| Name: |
Cytosolic phospholipase A2
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| Reactions: |
- 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
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| Gene Name: |
PLA2G4A |
| Uniprot ID: |
P47712 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase A2
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| Reactions: |
- phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
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| Gene Name: |
PLA2G1B |
| Uniprot ID: |
P04054 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase D2
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| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
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| Gene Name: |
PLD2 |
| Uniprot ID: |
O14939 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase D1
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| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
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| Gene Name: |
PLD1 |
| Uniprot ID: |
Q13393 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase D3
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| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
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| Gene Name: |
PLD3 |
| Uniprot ID: |
Q8IV08 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase D4
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| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
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| Gene Name: |
PLD4 |
| Uniprot ID: |
Q96BZ4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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