Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2017-09-09 03:37:30 UTC |
---|
Update Date | 2022-11-30 19:26:03 UTC |
---|
HMDB ID | HMDB0115106 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) |
---|
Description | PA(20:1(11Z)/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(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of eicosenoic 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)CCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C43H75O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,17-20,24,26,30,32,41H,3-11,13,15-16,21-23,25,27-29,31,33-40H2,1-2H3,(H2,46,47,48)/b14-12-,19-17-,20-18-,26-24-,32-30-/t41-/m1/s1 |
---|
Synonyms | Value | Source |
---|
1-eicosenoyl-2-arachidonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-eicosenoyl-2-arachidonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:1/20:4) | SMPDB, HMDB | PA(20:1n9/20:4n6) | SMPDB, HMDB | PA(20:1w9/20:4w6) | SMPDB, HMDB | PA(40:5) | SMPDB, HMDB | Phosphatidic acid(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) | SMPDB, HMDB | Phosphatidic acid(20:1/20:4) | SMPDB, HMDB | Phosphatidic acid(20:1n9/20:4n6) | SMPDB, HMDB | Phosphatidic acid(20:1w9/20:4w6) | SMPDB, HMDB | Phosphatidic acid(40:5) | SMPDB, HMDB | Phosphatidate(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) | SMPDB, HMDB | Phosphatidate(20:1/20:4) | SMPDB, HMDB | Phosphatidate(20:1n9/20:4n6) | SMPDB, HMDB | Phosphatidate(20:1w9/20:4w6) | SMPDB, HMDB | Phosphatidate(40:5) | SMPDB, HMDB | PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) | SMPDB |
|
---|
Chemical Formula | C43H75O8P |
---|
Average Molecular Weight | 751.039 |
---|
Monoisotopic Molecular Weight | 750.519956373 |
---|
IUPAC Name | [(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid |
---|
Traditional Name | (2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
---|
InChI Identifier | InChI=1S/C43H75O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,17-20,24,26,30,32,41H,3-11,13,15-16,21-23,25,27-29,31,33-40H2,1-2H3,(H2,46,47,48)/b14-12-,19-17-,20-18-,26-24-,32-30-/t41-/m1/s1 |
---|
InChI Key | CBPXLXSPDFLFBL-NRYPLOERSA-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(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0016011)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:1(11Z)) (PathBank: SMP0022835)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0022836)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0022837)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z)) (PathBank: SMP0022838)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0022839)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0022840)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)) (PathBank: SMP0022841)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0022842)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0022843)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0022844)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0022845)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0022846)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0022847)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0022848)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0022849)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:2(11Z,14Z)) (PathBank: SMP0034484)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0034485)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0067649)
- De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0) (PathBank: SMP0067656)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099991)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099992)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099993)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099994)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099995)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099996)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099997)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0/22:0) (PathBank: SMP0099998)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z)) (PathBank: SMP0099999)
- Cardiolipin Biosynthesis CL(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0100000)
|
---|
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(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5335.5 | Semi standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4692.1 | Standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5679.7 | Standard polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5316.9 | Semi standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4655.6 | Standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4972.1 | Standard polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5560.8 | Semi standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4793.2 | Standard non polar | 33892256 | PA(20:1(11Z)/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)CCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5671.2 | Standard polar | 33892256 |
|
---|
| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0udm-1152903600-48e502d931b4e5629575 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-0005-3295403100-040621663156f546a4c1 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0gba-1198105000-cfeadad11a829decaf60 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-054n-8089700600-64713d3862f273a678a8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-004i-9022000000-13cf9097d8052210d695 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-2c89ce43f471dbadbf4d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0002-0000000900-dccfdbdd55d97899a05d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0002-0006900400-13903e6f8d52af75ac12 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-0pb9-0009300000-7043f0b9fabc72735d04 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-00di-0000000900-4e68058f639f4a1afda3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-00i0-0000009900-b9a0e5abde079e70483b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-02pr-0000902300-5f86268efc3670bb9736 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0f89-0000000900-d8f32a3c09a28b1da180 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-0udi-0000005900-68faa2d50ad332a047a1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0udm-0000906200-ec6c067d3a914e3b5c81 | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|