Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:00:13 -0600 |
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Update Date | 2015-09-13 12:56:08 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | PA(16:0/16:0) |
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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 one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). |
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Structure | |
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Synonyms: | - 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphate
- 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate
- 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid
- 1,2-Dihexadecanoyl-rac-phosphatidate
- 1,2-Dihexadecanoyl-rac-phosphatidic acid
- 1,2-Dipalmitoyl-3-sn-phosphatidate
- 1,2-Dipalmitoyl-3-sn-phosphatidic acid
- 1,2-Dipalmitoyl-sn-glycerol 3-phosphate
- 1,2-Dipalmitoyl-sn-glycerol 3-phosphoric acid
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphate
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate
- 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid
- A 1,2-diacylglycerol-3-phosphate
- a 1,2-Diacylglycerol-3-phosphoric acid
- A 3-sn-phosphatidate
- a 3-sn-Phosphatidate
- a 3-sn-Phosphatidic acid
- A diacyl-glycerol-3p
- A diacyl-glycerol-p
- A diacylglycerol-3-phosphate
- a Diacylglycerol-3-phosphoric acid
- A phosphatidate
- A phosphatidic acid
- A phosphatidylglycerol
- An L-phosphatidate
- An L-phosphatidic acid
- DGP
- Diacylglycerol phosphate
- Diacylglycerol phosphoric acid
- Dipalmitoyl phosphatidate
- Dipalmitoyl-L-a-phosphatidate
- Dipalmitoyl-L-a-phosphatidic acid
- Dipalmitoyl-L-alpha-phosphatidate
- Dipalmitoyl-L-alpha-phosphatidic acid
- Dipalmitoyl-L-α-phosphatidate
- Dipalmitoyl-L-α-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
- L-α-Dipalmitoyl-phosphatidate
- L-α-Dipalmitoyl-phosphatidic acid
- L-α-Dipalmitoylphosphatidate
- L-α-Dipalmitoylphosphatidic acid
- PA(32:0)
- Phosphatidate(16:0/16:0)
- Phosphatidate(32:0)
- Phosphatidic acid(16:0/16:0)
- Phosphatidic acid(32:0)
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Chemical Formula: | C35H69O8P |
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Weight: | Average: 648.8913 Monoisotopic: 648.473005696 |
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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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CAS number: | 7091-44-3 |
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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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SMILES: | CCCCCCCCCCCCCCCC(=O)OC[C@H](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: | -2 |
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Melting point: | 161-165 °C |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-didodecanoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadec-9-enoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadecanoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dioctadec-11-enoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-Dioctadecanoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradec-7-enoylglycerol + PyrophosphateCytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradecanoylglycerol + PyrophosphateAdenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0)Adenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0)Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dioctadecanoyl, n-C18:0) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + PhosphateWater + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Phosphate1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoyl-ACP (n-C12:0ACP) > acyl carrier protein + PA(16:0/16:0)1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) > acyl carrier protein + PA(16:0/16:0)1-hexadecanoyl-sn-glycerol 3-phosphate + Palmitoyl-ACP (n-C16:0ACP) > acyl carrier protein + PA(16:0/16:0)1-Octadec-11-enoyl-sn-glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > acyl carrier protein + PA(16:0/16:0)1-Octadecanoyl-sn-glycerol 3-phosphate + Octadecanoyl-ACP (n-C18:0ACP) > acyl carrier protein + PA(16:0/16:0)1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1) > acyl carrier protein + PA(16:0/16:0)1-Tetradecanoyl-sn-glycerol 3-phosphate + Myristoyl-ACP (n-C14:0ACP) > acyl carrier protein + PA(16:0/16:0)Water + PA(16:0/16:0) > 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) + Hydrogen ionWater + PA(16:0/16:0) > 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Hexadecenoate (n-C16:1) Water + PA(16:0/16:0) > 1-hexadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Palmitic acidWater + PA(16:0/16:0) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)Water + PA(16:0/16:0) > 1-Octadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0)Water + PA(16:0/16:0) > 1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Tetradecenoate (N-C14:1)Water + PA(16:0/16:0) > 1-Tetradecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + tetradecanoate (n-C14:0)Water + PA(16:0/16:0) > 2-dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0)Water + PA(16:0/16:0) > 2-hexadec-9-enoyl-sn-glycerol 3-phosphate + Hexadecenoate (n-C16:1)Water + PA(16:0/16:0) > 2-hexadecanoyl-sn-glycerol 3-phosphate + Palmitic acidWater + PA(16:0/16:0) > 2-octadec-11-enoyl-sn-glycerol 3-phosphate + Octadecenoate (N-C18:1)Water + PA(16:0/16:0) > 2-octadecanoyl-sn-glycerol 3-phosphate + Octadecanoate (N-C18:0)Water + PA(16:0/16:0) > 2-tetradec-7-enoyl-sn-glycerol 3-phosphate + Tetradecenoate (N-C14:1)Water + PA(16:0/16:0) > 2-tetradecanoyl-sn-glycerol 3-phosphate + tetradecanoate (n-C14:0)CDP-1,2-didodecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-dihexadec-9-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-dihexadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-dioctadec-11-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-Dioctadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-ditetradec-7-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)CDP-1,2-ditetradecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (dioctadecanoyl, n-C18:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)CDP-diacylglycerol + Water <> Cytidine monophosphate + PA(16:0/16:0)Cytidine triphosphate + PA(16:0/16:0) <> Pyrophosphate + CDP-diacylglycerolAdenosine triphosphate + 1,2-Diacyl-sn-glycerol + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0)PA(16:0/16:0) + Coenzyme A + Acyl-CoA + 1-Acyl-sn-glycerol 3-phosphate <> 1-Acyl-sn-glycerol 3-phosphate + Acyl-CoAAcyl-[acyl-carrier protein] + 1-Acyl-sn-glycerol 3-phosphate <> Acyl-carrier protein + PA(16:0/16:0)a 1,2-diacyl-<i>sn</i>-glycerol 3-diphosphate + Water PA(16:0/16:0) + Phosphate + Hydrogen iona CDP-diacylglycerol + Water <> PA(16:0/16:0) + Cytidine monophosphate + Hydrogen ionCytidine triphosphate + PA(16:0/16:0) + Hydrogen ion > Pyrophosphate + a CDP-diacylglycerolAdenosine triphosphate + a 1,2-diacylglycerol <> Hydrogen ion + PA(16:0/16:0) + ADPa 1-acyl-<i>sn</i>-glycerol-3-phosphate + a long-chain acyl-CoA > Coenzyme A + PA(16:0/16:0)Adenosine triphosphate + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0)Cytidine triphosphate + PA(16:0/16:0) <> Pyrophosphate + CDP-diacylglycerolAdenosine triphosphate + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0) More...
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | |
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-9236341000-d0296e5b3dd53599a39d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0002-0000009000-b3b708036c56c15fec89 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-1492100000-5624ed03f664b67f79ec | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0a4i-1490000000-1ba8a217ef22599ee07c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0002-0002009000-7bdcaa7752c2e2970fdf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000900000-42187062de8aa3a7fcef | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a71-4092103000-08a70ad05021be172e3b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9050000000-dc7f569f98cd450257d0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-f628227e9a0ceffbeaf0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0000009000-8e723670c2d6da7d1500 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0000099000-cef7e1d91751b702106e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xr-0000946000-9592d132939363ae4ad4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000009000-5d6932d42201ac99e40a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052e-1166109000-3a40d8a06827026e1331 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1191101000-55ca7d5b11a7d0030aea | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001j-0000009000-6c5d51790d44b8f28697 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f6t-0000059000-f0c15a320524af660ac4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udl-0006093000-7e3d155745f467b43ae7 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Niedernberg, A., Tunaru, S., Blaukat, A., Ardati, A., Kostenis, E. (2003). "Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63." Cell Signal 15:435-446. Pubmed: 12618218
- Park KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26. Pubmed: 16185776
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Ando, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya. Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho (2001), 8 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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