Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-09-12 02:03:16 UTC |
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Update Date | 2022-11-30 19:03:45 UTC |
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HMDB ID | HMDB0009992 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) |
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Description | PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols phosphates 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 18 and 20 carbons are the most common. PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. |
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Structure | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C47H82O16P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)61-39(37-59-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-60-65(57,58)63-47-44(52)42(50)43(51)46(45(47)53)62-64(54,55)56/h11-14,17-19,21-22,24,39,42-47,50-53H,3-10,15-16,20,23,25-38H2,1-2H3,(H,57,58)(H2,54,55,56)/b13-11-,14-12-,19-17-,21-18-,24-22-/t39-,42?,43?,44?,45?,46-,47+/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate) | HMDB | 1-Linoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoinositol-phosphate | HMDB | 1-Linoleoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoinositol-phosphate | HMDB | 1-Phosphatidyl-1D-myo-inositol-4-phosphate | HMDB | Phosphatidylinositol phosphate(18:2/20:3) | HMDB | Phosphatidylinositol phosphate(18:2n6/20:3n6) | HMDB | Phosphatidylinositol phosphate(18:2W6/20:3W6) | HMDB | Phosphatidylinositol phosphate(38:5) | HMDB | PIP(18:2/20:3) | HMDB | PIP(18:2n6/20:3n6) | HMDB | PIP(18:2W6/20:3W6) | HMDB | PIP(38:5) | HMDB | PIP[3'](18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) | HMDB | 1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoinositol-phosphate | HMDB | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonate | HMDB | PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) | Lipid Annotator |
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Chemical Formula | C47H82O16P2 |
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Average Molecular Weight | 965.0919 |
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Monoisotopic Molecular Weight | 964.5078096 |
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IUPAC Name | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C47H82O16P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)61-39(37-59-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-60-65(57,58)63-47-44(52)42(50)43(51)46(45(47)53)62-64(54,55)56/h11-14,17-19,21-22,24,39,42-47,50-53H,3-10,15-16,20,23,25-38H2,1-2H3,(H,57,58)(H2,54,55,56)/b13-11-,14-12-,19-17-,21-18-,24-22-/t39-,42?,43?,44?,45?,46-,47+/m1/s1 |
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InChI Key | SCAYNZFOGSGBQW-HPSOQNNGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety. |
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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 | Glycerophosphoinositol phosphates |
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Direct Parent | Glycerophosphoinositol phosphates |
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Alternative Parents | |
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Substituents | - Glycerophosphoinositol phosphate
- Diacylglycerophosphoinositol
- Glycerophosphoinositol
- Inositol phosphate
- Cyclohexanol
- Fatty acid ester
- Dialkyl phosphate
- Monoalkyl phosphate
- Cyclitol or derivatives
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Fatty acyl
- Alkyl phosphate
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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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 IndicesNot Available |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-13 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-014i-7310002149-e359d672ee75e25161f9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-056v-8003012095-c27974ac5b0526744b7c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-001s-3698403000-43d8d44f3cf2b144c35a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-03di-0000001009-e1d861d86c320981d5fc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-01t9-7095007307-f97fec5194cf044a8f59 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PIP(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9011000002-91c03ab00cb51f854e8c | 2021-09-22 | Wishart Lab | View Spectrum |
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