| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-12-09 19:05:57 -0700 |
| Update Date |
2013-02-08 17:25:56 -0700 |
| HMDB ID |
HMDB11228 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PC(P-16:0/22:5(7Z,10Z,13Z,16Z,19Z)) |
| Description |
Phosphatidylcholines are a class of phospholipids which incorporate choline as a headgroup. They are a major component of biological membranes and can be isolated from either egg yolk (in Greek lekithos) or soy beans from which they are mechanically extracted or chemically extracted using hexane. Phosphatidylcholines are such a major component of lecithin, that, in some contexts, the terms are sometime used as synonyms. However, lecithin extract consists of a mixture of phosphatidylcholine and other compounds. It is also used along with sodium taurocholate for simulating fed- and fasted-state biorelevant media in dissolution studies of highly-lipophilic drugs. Phosphatidylcholine is a major constituent of cell membranes, and also plays a role in membrane-mediated cell signalling. Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol. Some medical researchers are experimenting with using Phosphatidylcholine in a type of injection that will break down fat cells; to be used as an alternative to liposuction known as Injection lipolysis. (Wikipedia). 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. 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
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2D Structure |
3D Structure
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| Synonyms |
- Phosphatidylcholine(dm16:0/22:5(7Z,10Z,13Z,16Z,19Z))
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| Chemical Formula |
C46H82NO7P |
| Average Molecular Weight |
792.1195 |
| Monoisotopic Molecular Weight |
791.582890495 |
| IUPAC Name |
(2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
| Traditional IUPAC Name |
(2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(1Z)-hexadec-1-en-1-yloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
| InChI Identifier |
InChI=1S/C46H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-46(48)54-45(44-53-55(49,50)52-42-40-47(3,4)5)43-51-41-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,27,29,38,41,45H,6-7,9,11-13,15,17-19,21,23,26,28,30-37,39-40,42-44H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,29-27-,41-38-/t45-/m1/s1 |
| InChI Key |
YINHBRYJXSJGGB-BXFGBEPMSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphocholines |
| Other Descriptors |
- Aliphatic Acyclic Compounds
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| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Choline
- Enol Ether
- Fatty Acid Ester
- Organic Hypophosphite
- Organic Phosphite
- Phosphocholine
- Phosphoethanolamine
- Phosphoric Acid Ester
- Quaternary Ammonium Salt
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| Direct Parent |
Other Glycerophosphocholines |
| 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 |
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| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027983 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767503  |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB11228 |
| Metagene Link |
HMDB11228 |
| METLIN ID |
Not Available |
| PubChem Compound |
53480697 |
| 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 |
| 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: |
Lecithin retinol acyltransferase
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| Reactions: |
- phosphatidylcholine + retinol---[cellular-retinol-binding-protein] = 2-acylglycerophosphocholine + retinyl-ester---[cellular-retinol-binding-protein] [RN:R04514]
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| Gene Name: |
LRAT |
| Uniprot ID: |
O95237 |
| 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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| Name: |
Phospholipase D6
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| Reactions: |
- a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
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| Gene Name: |
PLD6 |
| Uniprot ID: |
Q8N2A8 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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