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| Identification |
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| YMDB ID | YMDB01170 |
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| Name | PA(18:1(9Z)/0:0) |
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| Species | Saccharomyces cerevisiae |
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| Strain | Brewer's yeast |
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| Description | PA(18:1(9Z)/0:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids 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. PA(18:1(9Z)/0:0), in particular, consists of two 9Z-octadecenoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
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| Structure | |
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| Synonyms | - 1-Acyl-sn-glycerol 3-phosphate
- 2-Lysophosphatidate
- LPA
- Lysophosphatidate
- 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphate
- 1-O-Oleoyl-sn-glycerol 3-phosphate
- 1-O-Oleyl-sn-glycerol 3-phosphate
- 1-Oleoyl lysophosphatidic acid
- 1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidic acid
- 1-Oleoyl-sn-glycero-3-phosphate
- 1-Oleoylglycerol 3-phosphate
- 1-Oleyl-2-lyso-sn-glycerol 3-phosphatidic acid
- 1-Oleyl-sn-glycerol 3-phosphate
- 1-Oleylglycerol 3-phosphate
- 1-Oleyllysophosphatidic acid
- 18:1 LPA
- LPA 18:1
- LPA(18:1(9Z)/0:0)
- LPA(18:1)
- LPA(18:1/0:0)
- LPA(18:1n9/0:0)
- LPA(18:1W9/0:0)
- LysoPA(18:1(9Z)/0:0)
- LysoPA(18:1)
- LysoPA(18:1W9/0:0)
- Lysophosphatidic acid(18:1)
- Lysophosphatidic acid(18:1/0:0)
- Lysophosphatidic acid(18:1n9/0:0)
- Lysophosphatidic acid(18:1W9/0:0)
- Monooleylphosphatidic acid
- PA(18:1/0:0)
- 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphoric acid
- 1-O-Oleoyl-sn-glycerol 3-phosphoric acid
- 1-O-Oleyl-sn-glycerol 3-phosphoric acid
- 1-Oleoyl lysophosphatidate
- 1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidate
- 1-Oleoyl-sn-glycero-3-phosphoric acid
- 1-Oleoylglycerol 3-phosphoric acid
- 1-Oleyl-2-lyso-sn-glycerol 3-phosphatidate
- 1-Oleyl-sn-glycerol 3-phosphoric acid
- 1-Oleylglycerol 3-phosphoric acid
- 1-Oleyllysophosphatidate
- Lysophosphatidate(18:1)
- Lysophosphatidate(18:1/0:0)
- Lysophosphatidate(18:1n9/0:0)
- Lysophosphatidate(18:1W9/0:0)
- Monooleylphosphatidate
- 1-O-Oleyllysophosphatidic acid
- 9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl ester
- 1-Oleoyl-lyso-phosphatidic acid
- Monooleylphosphatidic acid, sodium salt, (R)-isomer
- 1-Oleoyl-lysophosphatidic acid
- LPA (lysophosphatidic acid)
- Lysophosphatidic acid
- Monooleylphosphatidic acid, (R)-isomer
- MOPA
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| CAS number | 22002-87-5 |
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| Weight | Average: 436.5198
Monoisotopic: 436.258990178 |
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| InChI Key | WRGQSWVCFNIUNZ-GDCKJWNLSA-N |
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| InChI | InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1 |
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| IUPAC Name | [(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid |
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| Traditional IUPAC Name | 1-oleoyl lysophosphatidic acid |
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| Chemical Formula | C21H41O7P |
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| SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphates |
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| Direct Parent | 1-acylglycerol-3-phosphates |
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| Alternative Parents | |
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| Substituents | - 1-acylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organooxygen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondrion membrane
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | |
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| SMPDB Reactions | Not Available |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | |
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| References |
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| References: | - Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Oshiro, J., Han, G. S., Carman, G. M. (2003). "Diacylglycerol pyrophosphate phosphatase in Saccharomyces cerevisiae." Biochim Biophys Acta 1635:1-9.14642771
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| Synthesis Reference: | Not Available |
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| External Links: | |
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