Record Information |
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Version | 1.0 |
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Created at | 2022-05-12 08:24:48 UTC |
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Updated at | 2022-05-12 08:24:48 UTC |
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NP-MRD ID | NP0122383 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | LPA(22:1(13Z)/0:0) |
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Description | LysoPA(22:1(13Z)/0:0), Also known as lpa(22:1) Or lpa(22:1(13Z)/0:0), Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Fatty acids containing 16 and 18 carbons are the most common. LysoPA(22:1(13Z)/0:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). It is the biosynthetic precursor of phosphatidic acid. LysoPA(22:1(13Z)/0:0) Is a lysophosphatidic acid. LysoPA(22:1(13Z)/0:0), In particular, consists of one chain of erucic acid at the C-1 position. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. It was first documented in 1992 (PMID: 1313792). Lysophosphatidic acid is the simplest possible glycerophospholipid (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
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Structure | CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O InChI=1S/C25H49O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h9-10,24,26H,2-8,11-23H2,1H3,(H2,28,29,30)/b10-9- |
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Synonyms | Value | Source |
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1-Erucoyl-glycero-3-phosphate | HMDB | 1-Erucoyl-lysophosphatidic acid | HMDB | LPA(22:1) | HMDB | LPA(22:1(13Z)) | HMDB | LPA(22:1n9/0:0) | HMDB | LPA(22:1W9/0:0) | HMDB | LPA(22:1n9) | HMDB | LPA(22:1W9) | HMDB | Lysophosphatidic acid(22:1(13Z)/0:0) | HMDB | Lysophosphatidic acid(22:1) | HMDB | Lysophosphatidic acid(22:1(13Z)) | HMDB | Lysophosphatidic acid(22:1n9/0:0) | HMDB | Lysophosphatidic acid(22:1W9/0:0) | HMDB | Lysophosphatidic acid(22:1n9) | HMDB | Lysophosphatidic acid(22:1W9) | HMDB | LPA(22:1(13Z)/0:0) | HMDB | LPA(22:1/0:0) | HMDB | Lysophosphatidic acid(22:1/0:0) | HMDB | 1-(13Z-Docosenoyl)-glycero-3-phosphate | HMDB | 1-(13Z-Docosenoyl)-phosphatidic acid | HMDB | 1-erucoyl-glycero-3-phosphate | SMPDB, HMDB | 1-erucoyl-lysophosphatidic acid | SMPDB, HMDB | LPA(22:1) | SMPDB, HMDB | LPA(22:1(13Z)) | SMPDB, HMDB | LPA(22:1n9/0:0) | SMPDB, HMDB | LPA(22:1w9/0:0) | SMPDB, HMDB | LPA(22:1n9) | SMPDB, HMDB | LPA(22:1w9) | SMPDB, HMDB | Lysophosphatidic acid(22:1(13Z)/0:0) | SMPDB, HMDB | Lysophosphatidic acid(22:1) | SMPDB, HMDB | Lysophosphatidic acid(22:1(13Z)) | SMPDB, HMDB | Lysophosphatidic acid(22:1n9/0:0) | SMPDB, HMDB | Lysophosphatidic acid(22:1w9/0:0) | SMPDB, HMDB | Lysophosphatidic acid(22:1n9) | SMPDB, HMDB |
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Chemical Formula | C25H49O7P |
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Average Mass | 492.6340 Da |
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Monoisotopic Mass | 492.32159 Da |
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IUPAC Name | {3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxy}phosphonic acid |
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Traditional Name | 3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O |
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InChI Identifier | InChI=1S/C25H49O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h9-10,24,26H,2-8,11-23H2,1H3,(H2,28,29,30)/b10-9- |
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InChI Key | UXYLIEZFFBAJAG-KTKRTIGZSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. |
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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-acylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1-acylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Alcohol
- 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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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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