| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2009-06-16 12:12:37 -0600 |
| Update Date |
2013-02-08 17:29:05 -0700 |
| HMDB ID |
HMDB12423 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PS(20:3(8Z,11Z,14Z)/18:1(9Z)) |
| Description |
PS(20:3(8Z,11Z,14Z)/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines 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. PS(20:3(8Z,11Z,14Z)/18:1(9Z)), in particular, consists of one chain of homo-g-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The homo-g-linolenic acid moiety is derived from fish oils, liver and kidney, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. 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. Phosphatidylserines typically carry a net charge of -1 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. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Homo-g-linolenoyl-2-oleoyl-sn-glycero-3-phosphoserine
- 1-Homo-gamma-linolenoyl-2-oleoyl-sn-glycero-3-phosphoserine
- Phosphatidylserine(20:3/18:1)
- Phosphatidylserine(20:3n6/18:1n9)
- Phosphatidylserine(20:3w6/18:1w9)
- Phosphatidylserine(38:4)
- PS(20:3/18:1)
- PS(20:3n6/18:1n9)
- PS(20:3w6/18:1w9)
- PS(38:4)
- PSer(20:3/18:1)
- PSer(20:3n6/18:1n9)
- PSer(20:3w6/18:1w9)
- PSer(38:4)
|
| Chemical Formula |
C44H78NO10P |
| Average Molecular Weight |
812.0646 |
| Monoisotopic Molecular Weight |
811.536334233 |
| IUPAC Name |
(2S)-2-amino-3-({hydroxy[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid |
| Traditional IUPAC Name |
(2S)-2-amino-3-{[hydroxy(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphoryl]oxy}propanoic acid |
| CAS Registry Number |
Not Available |
| SMILES |
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)C(O)=O |
| InChI Identifier |
InChI=1S/C44H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-42(46)52-37-40(38-53-56(50,51)54-39-41(45)44(48)49)55-43(47)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11,13,17-19,21-23,40-41H,3-10,12,14-16,20,24-39,45H2,1-2H3,(H,48,49)(H,50,51)/b13-11-,19-17-,21-18-,23-22-/t40-,41+/m1/s1 |
| InChI Key |
GXKSIBMRXCMFJL-HVMMZRTESA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphoserines |
| Other Descriptors |
- Aliphatic Acyclic Compounds
|
| Substituents |
- Acyclic Alkene
- Alpha Amino Acid Or Derivative
- Carboxylic Acid
- Carboxylic Acid Ester
- Fatty Acid Ester
- Organic Hypophosphite
- Organic Phosphite
- Phosphoethanolamine
- Phosphoric Acid Ester
- Primary Aliphatic Amine (Alkylamine)
- Tricarboxylic Acid Derivative
|
| Direct Parent |
Phosphatidylserines |
| 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 |
- All Tissues
- Kidney
- Liver
- Brain
- Heart
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.481 +/- 0.083 uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| 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 |
FDB029039 |
| 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 |
HMDB12423  |
| Metagene Link |
HMDB12423 |
| METLIN ID |
Not Available |
| PubChem Compound |
52925711 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
| Enzymes |
|---|
| Name: |
Group 10 secretory phospholipase A2
|
| Reactions: |
- Phosphatidylcholine + Water unknown 1-acylglycerophosphocholine + a carboxylate
- Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Fatty acid
- Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid
- Phosphatidylethanolamine + Water unknown 1-Acyl-sn-glycero-3-phosphoethanolamine + Fatty acid
- Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Linoleic acid
- O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water unknown 1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Carboxylate
- 1-Radyl-2-acyl-sn-glycero-3-phosphocholine + Water unknown 1-Organyl-2-lyso-sn-glycero-3-phosphocholine + Carboxylate
- Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Alpha-Linolenic acid
|
| Gene Name: |
PLA2G10 |
| Uniprot ID: |
O15496 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
2-acylglycerol O-acyltransferase 2
|
| Reactions: |
- Acyl-CoA + 2-acylglycerol unknown Coenzyme A + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
|
| Gene Name: |
MOGAT2 |
| Uniprot ID: |
Q3SYC2 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
| Name: |
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2
|
| Reactions: |
- 1-phosphatidyl-1D-myo-inositol 3,4,5-triphosphate + Water unknown 1-phosphatidyl-1D-myo-inositol 3,4-diphosphate + Phosphoric acid
- Phosphatidylinositol-3,4,5-trisphosphate + Water unknown 1-Phosphatidyl-1D-myo-inositol 3,4-bisphosphate + Phosphoric acid
|
| Gene Name: |
INPPL1 |
| Uniprot ID: |
O15357 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3
|
| Reactions: |
- 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + Water unknown Inositol 1,4,5-trisphosphate + DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
- 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate + Water unknown Inositol 1,4,5-trisphosphate + 1,2-Diacyl-sn-glycerol
|
| Gene Name: |
PLCD3 |
| Uniprot ID: |
Q8N3E9 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Sphingomyelin phosphodiesterase 3
|
| Reactions: |
- Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine
- Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine
|
| Gene Name: |
SMPD3 |
| Uniprot ID: |
Q9NY59 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
Sphingomyelin phosphodiesterase 4
|
| Reactions: |
- Sphingomyelin + Water unknown N-acylsphingosine + Phosphorylcholine
- Sphingomyelin + Water unknown N-Acylsphingosine + Phosphorylcholine
|
| Gene Name: |
SMPD4 |
| Uniprot ID: |
Q9NXE4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
