Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2008-09-12 02:04:23 UTC |
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Update Date | 2022-11-30 19:03:47 UTC |
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HMDB ID | HMDB0010058 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PIP2(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)) |
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Description | PIP2(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)) is a phosphatidylinositol bisphosphate. Phosphatidylinositol bisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a bisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol bisphosphates 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 bisphosphates 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. PIP2(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)), in particular, consists of one chain of (9Z,12Z-hexadecadienoate) at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The (9Z,12Z-hexadecadienoate) moiety is derived from fish oils, while the (10Z,13Z,16Z-docosatrienoyl) moiety is derived from fish oils. The most important phosphatidylinositol bisphosphate in both quantitative and biological terms is phosphatidylinositol 4,5-bisphosphate. 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/C\C=C/CCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCC)COP(O)(=O)O[C@H]1C(O)C(O)C(OP(=O)(O)O)[C@@H](OP(=O)(O)O)C1O InChI=1S/C47H83O19P3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(49)63-39(37-61-40(48)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58/h8,10-11,13-14,16-18,20-21,39,42-47,50-52H,3-7,9,12,15,19,22-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58)/b10-8-,13-11-,16-14-,18-17-,21-20-/t39-,42?,43?,44?,45+,46?,47+/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z,12Z-Hexadecadienoate | HMDB | 1-(9Z,12Z-Hexadecadienoate)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate) | HMDB | 1-(9Z,12Z-Hexadecadienoate)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phosphoinositol-bisphosphate | HMDB | 1-(9Z,12Z-Hexadecadienoic acid | HMDB | 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate | HMDB | Phosphatidylinositol diphosphate(16:2/22:3) | HMDB | Phosphatidylinositol diphosphate(16:2n4/22:3n6) | HMDB | Phosphatidylinositol diphosphate(16:2W4/22:3W6) | HMDB | Phosphatidylinositol diphosphate(38:5) | HMDB | PIP2(16:2/22:3) | HMDB | PIP2(16:2n4/22:3n6) | HMDB | PIP2(16:2W4/22:3W6) | HMDB | PIP2(38:5) | HMDB | PIP2[3',4'](16:2(9Z,12Z)/22:3(10Z,13Z,16Z)) | HMDB | {[(1S,3S)-3-({[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2,4,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonate | HMDB |
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Chemical Formula | C47H83O19P3 |
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Average Molecular Weight | 1045.0718 |
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Monoisotopic Molecular Weight | 1044.47414001 |
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IUPAC Name | {[(4S,6S)-4-({[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(4S,6S)-4-{[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2,3,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C\C=C/C\C=C/CCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCC)COP(O)(=O)O[C@H]1C(O)C(O)C(OP(=O)(O)O)[C@@H](OP(=O)(O)O)C1O |
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InChI Identifier | InChI=1S/C47H83O19P3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(49)63-39(37-61-40(48)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)38-62-69(59,60)66-45-42(50)43(51)46(64-67(53,54)55)47(44(45)52)65-68(56,57)58/h8,10-11,13-14,16-18,20-21,39,42-47,50-52H,3-7,9,12,15,19,22-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58)/b10-8-,13-11-,16-14-,18-17-,21-20-/t39-,42?,43?,44?,45+,46?,47+/m1/s1 |
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InChI Key | SJLOPHYYGZLTGX-OWFBGLHDSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol 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 | Phosphatidylinositol-4,5-bisphosphates |
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Alternative Parents | |
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Substituents | - Diacylglycerophosphoinositol-4,5-bisphosphate
- 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
- Carboxylic acid ester
- Secondary alcohol
- 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 | Not Available |
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Disposition | |
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Process | Not Available |
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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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