Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2017-09-09 03:43:14 UTC |
---|
Update Date | 2022-11-30 19:26:04 UTC |
---|
HMDB ID | HMDB0115141 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) |
---|
Description | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 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(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of mead acid at the C-1 position and one chain of clupanodonic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
---|
Structure | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C45H73O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,22,24-25,27-28,30-31,33,43H,3-4,6,8-10,12,14-16,21,23,26,29,32,34-42H2,1-2H3,(H2,48,49,50)/b7-5-,13-11-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t43-/m1/s1 |
---|
Synonyms | Value | Source |
---|
1-Meadoyl-2-clupanodonoyl-sn-glycero-3-phosphate | HMDB | 1-Meadoyl-2-clupanodonoyl-sn-phosphatidic acid | HMDB | PA(20:3/22:5) | HMDB | PA(20:3N9/22:5N3) | HMDB | PA(20:3W9/22:5W3) | HMDB | PA(42:8) | HMDB | Phosphatidic acid(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | HMDB | Phosphatidic acid(20:3/22:5) | HMDB | Phosphatidic acid(20:3n9/22:5n3) | HMDB | Phosphatidic acid(20:3W9/22:5W3) | HMDB | Phosphatidic acid(42:8) | HMDB | Phosphatidate(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | HMDB | Phosphatidate(20:3/22:5) | HMDB | Phosphatidate(20:3N9/22:5N3) | HMDB | Phosphatidate(20:3W9/22:5W3) | HMDB | Phosphatidate(42:8) | HMDB | [(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoyloxy]-3-[(8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphonate | HMDB | 1-meadoyl-2-clupanodonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-meadoyl-2-clupanodonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:3/22:5) | SMPDB, HMDB | PA(20:3n9/22:5n3) | SMPDB, HMDB | PA(20:3w9/22:5w3) | SMPDB, HMDB | PA(42:8) | SMPDB, HMDB | Phosphatidic acid(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidic acid(20:3/22:5) | SMPDB, HMDB | Phosphatidic acid(20:3n9/22:5n3) | SMPDB, HMDB | Phosphatidic acid(20:3w9/22:5w3) | SMPDB, HMDB | Phosphatidic acid(42:8) | SMPDB, HMDB | Phosphatidate(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidate(20:3/22:5) | SMPDB, HMDB | Phosphatidate(20:3n9/22:5n3) | SMPDB, HMDB | Phosphatidate(20:3w9/22:5w3) | SMPDB, HMDB | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB |
|
---|
Chemical Formula | C45H73O8P |
---|
Average Molecular Weight | 773.045 |
---|
Monoisotopic Molecular Weight | 772.504306309 |
---|
IUPAC Name | [(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphonic acid |
---|
Traditional Name | (2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphonic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
---|
InChI Identifier | InChI=1S/C45H73O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,22,24-25,27-28,30-31,33,43H,3-4,6,8-10,12,14-16,21,23,26,29,32,34-42H2,1-2H3,(H2,48,49,50)/b7-5-,13-11-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t43-/m1/s1 |
---|
InChI Key | HAJRGNHBJYXQSV-NLJKXUEXSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphates |
---|
Direct Parent | 1,2-diacylglycerol-3-phosphates |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0067939)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0067940)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0) (PathBank: SMP0076688)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) (PathBank: SMP0067942)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0023369)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:1(13Z)) (PathBank: SMP0023370)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0023372)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0023373)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0023374)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:2(13Z,16Z)) (PathBank: SMP0023375)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0023376)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0023377)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0023378)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0023379)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0023380)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0023381)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)) (PathBank: SMP0034936)
- De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0034937)
|
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
---|
PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5821.4 | Standard polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 4803.4 | Standard non polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5523.0 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5573.1 | Semi standard non polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4891.5 | Standard non polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5324.0 | Standard polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5783.9 | Semi standard non polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5008.6 | Standard non polar | 33892256 | PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5354.3 | Standard polar | 33892256 |
|
---|
| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-022l-1169802600-8c3343ca717a0b271261 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-01p2-2297402100-afeddc74564e13ac0569 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-01p2-1198001100-c57bc680e71d50437003 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-05dr-5049400300-5bf280e8a5dfaa06a7d1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004i-9023000000-af736d7817bd502cf76c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-9000000000-b002f5529fef0a58c8e0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0ab9-0000000900-bb363daa0f3f6a82a5b3 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-00fr-0000005900-25cb0078d2d3f9216052 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-00ou-0000906200-172acf62cb2084b355a7 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0002-0000000900-cbc1cd56af332dabbc21 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0002-0000009900-9a87808e159835245062 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-00kk-0000922400-5dafc7be3c93a6b7a2dc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-00di-0000000900-71d326626d4a2c53022f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-062f-0006900400-28fb017203bb642c8913 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-0a6r-0009300000-96acb20bb32345bbf71c | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|