Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 04:36:11 UTC |
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Update Date | 2022-11-30 19:26:11 UTC |
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HMDB ID | HMDB0115399 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) |
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Description | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 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(22:5(7Z,10Z,13Z,16Z,19Z)/24:0), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
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Structure | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C49H87O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-28-30-32-34-36-38-40-42-44-49(51)57-47(46-56-58(52,53)54)45-55-48(50)43-41-39-37-35-33-31-29-27-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,25,27,31,33,47H,3-5,7,9-11,13,15-17,19,21-24,26,28-30,32,34-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,20-18-,27-25-,33-31-/t47-/m1/s1 |
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Synonyms | Value | Source |
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1-clupanodonoyl-2-lignoceroyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-clupanodonoyl-2-lignoceroyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:5/24:0) | SMPDB, HMDB | PA(22:5n3/24:0) | SMPDB, HMDB | PA(22:5w3/24:0) | SMPDB, HMDB | PA(46:5) | SMPDB, HMDB | Phosphatidic acid(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | SMPDB, HMDB | Phosphatidic acid(22:5/24:0) | SMPDB, HMDB | Phosphatidic acid(22:5n3/24:0) | SMPDB, HMDB | Phosphatidic acid(22:5w3/24:0) | SMPDB, HMDB | Phosphatidic acid(46:5) | SMPDB, HMDB | Phosphatidate(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | SMPDB, HMDB | Phosphatidate(22:5/24:0) | SMPDB, HMDB | Phosphatidate(22:5n3/24:0) | SMPDB, HMDB | Phosphatidate(22:5w3/24:0) | SMPDB, HMDB | Phosphatidate(46:5) | SMPDB, HMDB | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | SMPDB | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoyloxy]-2-(tetracosanoyloxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C49H87O8P |
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Average Molecular Weight | 835.201 |
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Monoisotopic Molecular Weight | 834.613856759 |
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IUPAC Name | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(tetracosanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(tetracosanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C49H87O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-28-30-32-34-36-38-40-42-44-49(51)57-47(46-56-58(52,53)54)45-55-48(50)43-41-39-37-35-33-31-29-27-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,25,27,31,33,47H,3-5,7,9-11,13,15-17,19,21-24,26,28-30,32,34-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,20-18-,27-25-,33-31-/t47-/m1/s1 |
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InChI Key | PJDKNNWVKKWYRY-XSTMBPSBSA-N |
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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 | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0026093)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0026094)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:0) (PathBank: SMP0068391)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z)) (PathBank: SMP0068392)
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5635.6 | Standard polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5303.9 | Standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5956.8 | Semi standard non polar | 33892256 |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 10V, Positive-QTOF | splash10-0hg9-1009310240-300e265341fc965da2b4 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 20V, Positive-QTOF | splash10-11os-1119210100-5fcdef87473ff2b1b7ed | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 40V, Positive-QTOF | splash10-00dr-0029100100-ca303c56af81c328f8de | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 10V, Negative-QTOF | splash10-02e9-3009200020-ec0e722ce590b6250623 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 20V, Negative-QTOF | splash10-004i-9005000000-f8bdf9103333db666fe1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 40V, Negative-QTOF | splash10-004i-9000000000-d1710cacb9af745e5b55 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 10V, Negative-QTOF | splash10-001i-0000000090-28c52e887a47347da2b4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 20V, Negative-QTOF | splash10-0ge9-1109750060-5f87ec4c9025a606ca39 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 40V, Negative-QTOF | splash10-00or-0009110000-bef0534e89b21ef29cf0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 10V, Positive-QTOF | splash10-014r-0000000090-37b962ab656bd6de090c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 20V, Positive-QTOF | splash10-000i-0000000590-ceaf67056691155e4756 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 40V, Positive-QTOF | splash10-05n0-0000660930-653421c56c5c132691ba | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 10V, Positive-QTOF | splash10-0a4i-0000000090-6588047845a33c245ea2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 20V, Positive-QTOF | splash10-0a4i-0000000990-6dff0f00a47691a04507 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:0) 40V, Positive-QTOF | splash10-0a4r-0000390340-bae9a3040bdf74cc469d | 2021-09-23 | Wishart Lab | View Spectrum |
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