| Identification |
|---|
| YMDB ID | YMDB13365 |
|---|
| Name | Lyso-PS(0:0/14:0) |
|---|
| Species | Saccharomyces cerevisiae |
|---|
| Strain | Brewer's yeast |
|---|
| Description | Lyso-PS(0:0/14:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PS(0:0/14:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylserines (LPSs) enhance glucose transport, lowering blood glucose levels while leaving secretion of insulin unaffected. LPSs have been known as a signaling phospholipid in mast cell biology. They enhance stimulated histamine release and eicosanoid production. LPSs also play a roles in the promotion of phagocytosis of apoptotic cells and resolution of inflammation. |
|---|
| Structure | |
|---|
| Synonyms | Not Available |
|---|
| CAS number | Not Available |
|---|
| Weight | Average: 468.504
Monoisotopic: 468.236792418 |
|---|
| InChI Key | TZPRMIGZGQOWBD-UHFFFAOYSA-M |
|---|
| InChI | InChI=1S/C20H40NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(23)30-17(14-22)15-28-31(26,27)29-16-18(21)20(24)25/h17-18,22H,2-16,21H2,1H3,(H,24,25)(H,26,27)/p-1 |
|---|
| IUPAC Name | 2-azaniumyl-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate |
|---|
| Traditional IUPAC Name | 2-ammonio-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate |
|---|
| Chemical Formula | C20H39NO9P |
|---|
| SMILES | CCCCCCCCCCCCCC(=O)OC(CO)COP([O-])(=O)OCC([NH3+])C([O-])=O |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as 2-acyl-glycerol-3-phosphoserines. These are monoacylglycerol-3-phosphoserines with a fatty acyl chain linked to the O2-atom of the glycerol moiety. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Glycerophospholipids |
|---|
| Sub Class | Glycerophosphoserines |
|---|
| Direct Parent | 2-acyl-glycerol-3-phosphoserines |
|---|
| Alternative Parents | |
|---|
| Substituents | - 2-monoacyl-glycerol-3-phosphoserine
- Alpha-amino acid or derivatives
- Alpha-amino acid
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Dicarboxylic acid or derivatives
- Amino acid
- Carboxylic acid ester
- Amino acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Alcohol
- Organic anion
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Charge | -1 |
|---|
| Melting point | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
|
|---|
| Predicted Properties | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Organoleptic Properties | Not Available |
|---|
| SMPDB Pathways | | Lysolipid incorporation into ER | PW002532 |    | | Lysolipid incorporation into ER PC(14:0/14:0) | PW002783 |    | | Lysolipid incorporation into Mitochondria | PW002531 |    | | Lysolipid incorporation into Mitochondria PC(14:0/14:0) | PW002792 |    |
|
|---|
| KEGG Pathways | Not Available |
|---|
| SMPDB Reactions | |
|---|
| KEGG Reactions | Not Available |
|---|
| Concentrations |
|---|
| Intracellular Concentrations | Not Available |
|---|
| Extracellular Concentrations | Not Available |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0gdl-1491800000-a63c22848279bd97add4 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fvi-2942100000-5a11ee2b14bbc068a6b5 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003r-9520000000-51d27c33bd9dcb3202f0 | JSpectraViewer |
|
|---|
| References |
|---|
| References: | - Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
|
|---|
| Synthesis Reference: | Not Available |
|---|
| External Links: | | Resource | Link |
|---|
| CHEBI ID | Not Available | | HMDB ID | Not Available | | Pubchem Compound ID | Not Available | | Kegg ID | Not Available | | ChemSpider ID | Not Available | | FOODB ID | Not Available | | Wikipedia ID | Not Available | | BioCyc ID | Not Available |
|
|---|
