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 06:23:17 UTC |
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Update Date | 2022-11-30 19:26:23 UTC |
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HMDB ID | HMDB0115902 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(i-22:0/8:0) |
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Description | PA(i-22:0/8:0) 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(i-22:0/8:0), in particular, consists of one chain of isodocosanoic acid at the C-1 position and one chain of caprylic 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)CCCCCCCCCCCCCCCCCCC(C)C)(COP(O)(O)=O)OC(=O)CCCCCCC InChI=1S/C33H65O8P/c1-4-5-6-19-24-27-33(35)41-31(29-40-42(36,37)38)28-39-32(34)26-23-21-18-16-14-12-10-8-7-9-11-13-15-17-20-22-25-30(2)3/h30-31H,4-29H2,1-3H3,(H2,36,37,38)/t31-/m1/s1 |
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Synonyms | Value | Source |
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1-isodocosanoyl-2-capryloyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-isodocosanoyl-2-capryloyl-sn-phosphatidic acid | SMPDB, HMDB | PA(i-22:0/8:0) | SMPDB | PA(30:0) | SMPDB, HMDB | Phosphatidic acid(i-22:0/8:0) | SMPDB, HMDB | Phosphatidic acid(30:0) | SMPDB, HMDB | Phosphatidate(i-22:0/8:0) | SMPDB, HMDB | Phosphatidate(30:0) | SMPDB, HMDB | [(2R)-3-[(20-Methylhenicosanoyl)oxy]-2-(octanoyloxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C33H65O8P |
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Average Molecular Weight | 620.849 |
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Monoisotopic Molecular Weight | 620.441706051 |
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IUPAC Name | [(2R)-3-[(20-methylhenicosanoyl)oxy]-2-(octanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(20-methylhenicosanoyl)oxy]-2-(octanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)(COP(O)(O)=O)OC(=O)CCCCCCC |
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InChI Identifier | InChI=1S/C33H65O8P/c1-4-5-6-19-24-27-33(35)41-31(29-40-42(36,37)38)28-39-32(34)26-23-21-18-16-14-12-10-8-7-9-11-13-15-17-20-22-25-30(2)3/h30-31H,4-29H2,1-3H3,(H2,36,37,38)/t31-/m1/s1 |
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InChI Key | HDKMBQANZGEWRP-WJOKGBTCSA-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 | |
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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(i-22:0/8:0),1TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 4264.4 | Semi standard non polar | 33892256 | PA(i-22:0/8:0),1TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 3808.7 | Standard non polar | 33892256 | PA(i-22:0/8:0),1TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 5269.9 | Standard polar | 33892256 | PA(i-22:0/8:0),2TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4266.9 | Semi standard non polar | 33892256 | PA(i-22:0/8:0),2TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3839.0 | Standard non polar | 33892256 | PA(i-22:0/8:0),2TMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4586.2 | Standard polar | 33892256 | PA(i-22:0/8:0),1TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4490.9 | Semi standard non polar | 33892256 | PA(i-22:0/8:0),1TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 3938.6 | Standard non polar | 33892256 | PA(i-22:0/8:0),1TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5269.9 | Standard polar | 33892256 | PA(i-22:0/8:0),2TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4749.1 | Semi standard non polar | 33892256 | PA(i-22:0/8:0),2TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4050.9 | Standard non polar | 33892256 | PA(i-22:0/8:0),2TBDMS,isomer #1 | CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4682.6 | 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(i-22:0/8:0) 10V, Positive-QTOF | splash10-00fr-3936536000-70892cd39a5d5272286d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 20V, Positive-QTOF | splash10-00c1-9846220000-15903173684a447f58b3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 40V, Positive-QTOF | splash10-0002-9235020000-1ed422c7541a16dd79ca | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 10V, Negative-QTOF | splash10-00vu-4309303000-5b4c785666cf5f380ccd | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 20V, Negative-QTOF | splash10-004i-9104000000-9aef60b72102a82af7d8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 40V, Negative-QTOF | splash10-004i-9000000000-7c2b6f90d654078ecd43 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 10V, Positive-QTOF | splash10-0uk9-0000009000-70aa8e33cde77745a7a5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 20V, Positive-QTOF | splash10-00di-0000059000-ead56966e85a342e7135 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 40V, Positive-QTOF | splash10-00gi-0060693000-ffd86175d2d4c18ed579 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 10V, Negative-QTOF | splash10-014i-0000009000-7034fdc92b1f97d5a103 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 20V, Negative-QTOF | splash10-00or-1665907000-ec4431d262460404b171 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 40V, Negative-QTOF | splash10-002u-1739301000-ddfe068158f5ec81fbc1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 10V, Positive-QTOF | splash10-0006-0000009000-0fced86a21500373c9c1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 20V, Positive-QTOF | splash10-0008-0000099000-69ae50cbbe469c0137f9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-22:0/8:0) 40V, Positive-QTOF | splash10-0fdn-0009586000-93b77017fe251ca12d5b | 2021-09-25 | Wishart Lab | View Spectrum |
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