Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 13:36:05 UTC |
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Updated at | 2022-09-09 13:36:05 UTC |
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NP-MRD ID | NP0285432 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid |
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Description | PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as PA(18:0/22:6), 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. Thus, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphate lipid molecule. PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions. In particular, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from lpa(18:0/0:0) And docosahexaenoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In addition, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); Which is mediated by the enzyme phosphatidate phosphatase. (2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid is found in Trypanosoma brucei. In humans, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway. |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3,(H2,46,47,48)/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1 |
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Synonyms | Value | Source |
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(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate | ChEBI | 1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphate | ChEBI | 1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate | ChEBI | PA(18:0/22:6) | ChEBI | (2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid | Generator | 1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphoric acid | Generator | 1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoric acid | Generator | 1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-stearoyl-2-docosahexaenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:0/22:6) | SMPDB, ChEBI | PA(18:0/22:6n3) | SMPDB, HMDB | PA(18:0/22:6w3) | SMPDB, HMDB | PA(40:6) | SMPDB, HMDB | Phosphatidic acid(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidic acid(18:0/22:6) | SMPDB, HMDB | Phosphatidic acid(18:0/22:6n3) | SMPDB, HMDB | Phosphatidic acid(18:0/22:6w3) | SMPDB, HMDB | Phosphatidic acid(40:6) | SMPDB, HMDB | Phosphatidate(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidate(18:0/22:6) | SMPDB, HMDB | Phosphatidate(18:0/22:6n3) | SMPDB, HMDB | Phosphatidate(18:0/22:6w3) | SMPDB, HMDB | Phosphatidate(40:6) | SMPDB, HMDB | PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB |
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Chemical Formula | C43H73O8P |
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Average Mass | 749.0230 Da |
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Monoisotopic Mass | 748.50431 Da |
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IUPAC Name | [(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3,(H2,46,47,48)/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1 |
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InChI Key | SFHGEOGVGJYLEK-USQBYQOHSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 | |
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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 | |
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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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