Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2017-09-09 02:48:30 UTC |
---|
Update Date | 2022-11-30 19:25:55 UTC |
---|
HMDB ID | HMDB0114821 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | PA(15:0/20:4(5Z,8Z,11Z,14Z)) |
---|
Description | PA(15:0/20:4(5Z,8Z,11Z,14Z)) 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(15:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of arachidonic 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)CCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C38H67O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-38(40)46-36(35-45-47(41,42)43)34-44-37(39)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,25,27,36H,3-10,12,14-16,19,22-24,26,28-35H2,1-2H3,(H2,41,42,43)/b13-11-,18-17-,21-20-,27-25-/t36-/m1/s1 |
---|
Synonyms | Value | Source |
---|
1-pentadecanoyl-2-arachidonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-pentadecanoyl-2-arachidonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(15:0/20:4) | SMPDB, HMDB | PA(15:0/20:4n6) | SMPDB, HMDB | PA(15:0/20:4w6) | SMPDB, HMDB | PA(35:4) | SMPDB, HMDB | Phosphatidic acid(15:0/20:4(5Z,8Z,11Z,14Z)) | SMPDB, HMDB | Phosphatidic acid(15:0/20:4) | SMPDB, HMDB | Phosphatidic acid(15:0/20:4n6) | SMPDB, HMDB | Phosphatidic acid(15:0/20:4w6) | SMPDB, HMDB | Phosphatidic acid(35:4) | SMPDB, HMDB | Phosphatidate(15:0/20:4(5Z,8Z,11Z,14Z)) | SMPDB, HMDB | Phosphatidate(15:0/20:4) | SMPDB, HMDB | Phosphatidate(15:0/20:4n6) | SMPDB, HMDB | Phosphatidate(15:0/20:4w6) | SMPDB, HMDB | Phosphatidate(35:4) | SMPDB, HMDB | PA(15:0/20:4(5Z,8Z,11Z,14Z)) | SMPDB |
|
---|
Chemical Formula | C38H67O8P |
---|
Average Molecular Weight | 682.92 |
---|
Monoisotopic Molecular Weight | 682.457356115 |
---|
IUPAC Name | [(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(pentadecanoyloxy)propoxy]phosphonic acid |
---|
Traditional Name | (2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-(pentadecanoyloxy)propoxyphosphonic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
---|
InChI Identifier | InChI=1S/C38H67O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-38(40)46-36(35-45-47(41,42)43)34-44-37(39)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,25,27,36H,3-10,12,14-16,19,22-24,26,28-35H2,1-2H3,(H2,41,42,43)/b13-11-,18-17-,21-20-,27-25-/t36-/m1/s1 |
---|
InChI Key | BEPRYOCGOJPVSH-BMMUJZTPSA-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 | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | Not Available |
---|
Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/15:0) (PathBank: SMP0017354)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/16:0) (PathBank: SMP0017355)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:0) (PathBank: SMP0017356)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:0) (PathBank: SMP0017357)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0017358)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:0) (PathBank: SMP0017359)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/14:1(9Z)) (PathBank: SMP0017360)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0017361)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0017362)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0017363)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:1(11Z)) (PathBank: SMP0017364)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0017365)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0017366)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z)) (PathBank: SMP0017367)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0017368)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0017369)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0017370)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)) (PathBank: SMP0017371)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0017372)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0017373)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0017374)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0017375)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0017376)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0017377)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0017378)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0017379)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:2(11Z,14Z)) (PathBank: SMP0032705)
- De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0032706)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0098204)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098205)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0098206)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0098207)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098208)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0098209)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0098210)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/22:0/22:0) (PathBank: SMP0098211)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z)) (PathBank: SMP0098212)
- Cardiolipin Biosynthesis CL(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0098213)
|
---|
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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4835.0 | Semi standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4304.5 | Standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5526.9 | Standard polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4801.5 | Semi standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4282.0 | Standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4796.2 | Standard polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5053.4 | Semi standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4414.1 | Standard non polar | 33892256 | PA(15:0/20:4(5Z,8Z,11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5508.8 | Standard polar | 33892256 |
|
---|
| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-005i-1195215000-804ba00d0876b42ccaf2 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-005j-2392111000-7ca311889c069a7cfafa | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-000t-1390011000-1894474312db5f11697f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0fiu-4095002000-078ab06c48b8c0ecb7cb | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-004i-9040000000-ac60769620ca8457dda3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-665e29644cb53b78372d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0159-0000009000-d84dab4b7e3e59ed157b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-001r-0000059000-9bda4195cec1de516415 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-002u-0006693000-139197130afcf20a0b7d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-001i-0000009000-1ce6be7a6c4d1a76be7f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0fcc-0039404000-299ac3a38bfe4a076b25 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-0f6x-1189301000-c4d91e0a5a30f83cc55b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0a4i-0000000900-c67867f070d20afed706 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-0a4i-0000009900-b880114dd8e71a8deef9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(15:0/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0r00-0000902300-ca9876c2be4408cbf8aa | 2021-09-24 | Wishart Lab | View Spectrum |
|
---|