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Identification |
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YMDB ID | YMDB01161 |
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Name | PA(16:0/16:0) |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | PA(16:0/16:0)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(16:0/16:0), in particular, consists of two hexadecanoyl 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 | - 1,2-dihexadecanoyl-rac-phosphatidic acid
- 1,2-dipalmitoyl-rac-glycero-3-phosphate
- PA(16:0/16:0)
- PA(32:0)
- Phosphatidic Acid(16:0/16:0)
- Phosphatidic Acid(32:0)
- 1,2-Dipalmitoyl-3-sn-phosphatidic acid
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphate
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid
- Dipalmitoyl phosphatidic acid
- 1,2-Dipalmitoyl-3-sn-phosphatidate
- Dipalmitoyl phosphatidate
- Phosphatidate(16:0/16:0)
- Phosphatidate(32:0)
- 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate
- 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid
- 1,2-Dipalmitoyl-sn-glycerol 3-phosphate
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate
- Dipalmitoyl-L-a-phosphatidate
- Dipalmitoyl-L-a-phosphatidic acid
- Dipalmitoyl-L-alpha-phosphatidate
- Dipalmitoyl-L-alpha-phosphatidic acid
- Dipalmitoylphosphatidate
- Dipalmitoylphosphatidic acid
- L-a-Dipalmitoyl-phosphatidate
- L-a-Dipalmitoyl-phosphatidic acid
- L-a-Dipalmitoylphosphatidate
- L-a-Dipalmitoylphosphatidic acid
- L-alpha-Dipalmitoyl-phosphatidate
- L-alpha-Dipalmitoyl-phosphatidic acid
- L-alpha-Dipalmitoylphosphatidate
- L-alpha-Dipalmitoylphosphatidic acid
- Dipalmitoylphosphatidic acid, calcium salt
- Dipalmitoylphosphatidic acid, ammonium salt
- 1,2-Dipalmitoyl-sn-glycero-3-phosphate
- Dipalmitoylphosphatidic acid, sodium salt
- Dipalmitoylphosphatidic acid, (+-)-isomer
- Dipalmitoylphosphatidic acid, (R)-isomer
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CAS number | 169051-60-9 |
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Weight | Average: 648.903 Monoisotopic: 648.47300618 |
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InChI Key | PORPENFLTBBHSG-MGBGTMOVSA-N |
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InChI | InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1 |
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IUPAC Name | [(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid |
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Traditional IUPAC Name | dipalmitoyl |
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Chemical Formula | C35H69O8P |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. |
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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 | 1,2-diacylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- 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 | Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:1(11Z)) | PW012433 | | Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:1(9Z)) | PW012434 | | Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/24:0) | PW012435 | | Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/24:1(11Z)) | PW012436 | | Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/24:1(9Z)) | PW012437 | |
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KEGG Pathways | Glycerophospholipid metabolism | ec00564 | |
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SMPDB Reactions |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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99500 ± 1750 umol/L | SD media with 2% raffinose | 37 oC | BY4741 | PMID: 19174513 | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-9236341000-d0296e5b3dd53599a39d | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0002-0000009000-b3b708036c56c15fec89 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-1492100000-5624ed03f664b67f79ec | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0a4i-1490000000-1ba8a217ef22599ee07c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0002-0002009000-7bdcaa7752c2e2970fdf | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000900000-42187062de8aa3a7fcef | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a71-4092103000-08a70ad05021be172e3b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9050000000-dc7f569f98cd450257d0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-f628227e9a0ceffbeaf0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0000009000-8e723670c2d6da7d1500 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0000099000-cef7e1d91751b702106e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xr-0000946000-9592d132939363ae4ad4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000009000-5d6932d42201ac99e40a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052e-1166109000-3a40d8a06827026e1331 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1191101000-55ca7d5b11a7d0030aea | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001j-0000009000-6c5d51790d44b8f28697 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f6t-0000059000-f0c15a320524af660ac4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udl-0006093000-7e3d155745f467b43ae7 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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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
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Synthesis Reference: | Not Available |
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External Links: | |
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