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 04:12:30 UTC |
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Update Date | 2022-11-30 19:26:07 UTC |
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HMDB ID | HMDB0115274 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:1(13Z)/16:1(9Z)) |
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Description | PA(22:1(13Z)/16:1(9Z)) 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(22:1(13Z)/16:1(9Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of palmitoleic 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)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C41H77O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h14,16-18,39H,3-13,15,19-38H2,1-2H3,(H2,44,45,46)/b16-14-,18-17-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-erucoyl-2-palmitoleoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-erucoyl-2-palmitoleoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:1/16:1) | SMPDB, HMDB | PA(22:1n9/16:1n7) | SMPDB, HMDB | PA(22:1w9/16:1w7) | SMPDB, HMDB | PA(38:2) | SMPDB, HMDB | Phosphatidic acid(22:1(13Z)/16:1(9Z)) | SMPDB, HMDB | Phosphatidic acid(22:1/16:1) | SMPDB, HMDB | Phosphatidic acid(22:1n9/16:1n7) | SMPDB, HMDB | Phosphatidic acid(22:1w9/16:1w7) | SMPDB, HMDB | Phosphatidic acid(38:2) | SMPDB, HMDB | Phosphatidate(22:1(13Z)/16:1(9Z)) | SMPDB, HMDB | Phosphatidate(22:1/16:1) | SMPDB, HMDB | Phosphatidate(22:1n9/16:1n7) | SMPDB, HMDB | Phosphatidate(22:1w9/16:1w7) | SMPDB, HMDB | Phosphatidate(38:2) | SMPDB, HMDB | PA(22:1(13Z)/16:1(9Z)) | SMPDB | [(2R)-3-[(13Z)-Docos-13-enoyloxy]-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C41H77O8P |
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Average Molecular Weight | 729.033 |
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Monoisotopic Molecular Weight | 728.535606437 |
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IUPAC Name | [(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-hexadec-9-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC |
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InChI Identifier | InChI=1S/C41H77O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h14,16-18,39H,3-13,15,19-38H2,1-2H3,(H2,44,45,46)/b16-14-,18-17-/t39-/m1/s1 |
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InChI Key | CNYMPPYTQKSGDS-HNNDRFCVSA-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(22:1(13Z)/16:1(9Z)/22:1(13Z)) (PathBank: SMP0023511)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/24:1(15Z)) (PathBank: SMP0023512)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0023513)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0023514)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0023515)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/22:2(13Z,16Z)) (PathBank: SMP0023516)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0023517)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0023518)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0023519)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0023520)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0023521)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0023522)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0023523)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0023524)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/20:2(11Z,14Z)) (PathBank: SMP0036835)
- De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/16:1(9Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0036836)
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:1(13Z)/16:1(9Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5156.5 | Semi standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4520.7 | Standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5836.6 | Standard polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5080.0 | Semi standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4494.5 | Standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5060.4 | Standard polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5395.9 | Semi standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4613.0 | Standard non polar | 33892256 | PA(22:1(13Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\CCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5821.2 | Standard 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(22:1(13Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-004r-1179403500-27bc8661be29714d686a | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-00bj-3298213100-7334dc9da4272fedcf19 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-002b-1298034000-d8f464a7cd56cf25f1cf | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 10V, Negative-QTOF | splash10-00p0-4039300300-d30008e7131d1eaf2d32 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 20V, Negative-QTOF | splash10-004i-9014000000-692db74ecb4234cdb4d3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 40V, Negative-QTOF | splash10-004i-9000000000-42f9387129f20f6e9a17 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-0udi-0000000900-f0b905cf11c47200d7a6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-0udi-0000009900-288397fd57e3bf8c6948 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-0w31-0000922400-79c5f1fa38f26ab242ff | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 10V, Negative-QTOF | splash10-004i-0000000900-78de2b4b1a87619ed0a4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 20V, Negative-QTOF | splash10-0fg9-1149900600-ead608531b5a248c3ee2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 40V, Negative-QTOF | splash10-0f79-1159300100-41ff6845cb0dfc3547ae | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-03fr-0000000900-d2b1917d92b4e8adf248 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-0059-0000005900-f502046e66db245b43b1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:1(13Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-003u-0006609300-8e94beb786b9415785a2 | 2021-09-25 | Wishart Lab | View Spectrum |
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