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 02:02:45 UTC |
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Update Date | 2022-11-30 19:03:44 UTC |
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HMDB ID | HMDB0009962 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PIP(18:1(11Z)/18:1(9Z)) |
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Description | PIP(18:1(11Z)/18:1(9Z)) 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(18:1(11Z)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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 | CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O InChI=1S/C45H84O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h13,15,18,20,37,40-45,48-51H,3-12,14,16-17,19,21-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b15-13-,20-18-/t37-,40?,41?,42?,43?,44-,45+/m1/s1 |
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Synonyms | Value | Source |
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Phosphatidylinositol phosphate(36:2) | HMDB | Phosphatidylinositol phosphate(18:1/18:1) | HMDB | 1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate) | HMDB | PIP(36:2) | HMDB | PIP[3'](18:1(11Z)/18:1(9Z)) | HMDB | PIP(18:1/18:1) | HMDB | 1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoinositol-phosphate | HMDB | 1-Vaccenoyl-2-oleoyl-sn-glycero-3-phosphoinositol-phosphate | HMDB | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonate | HMDB | PIP(18:1(11Z)/18:1(9Z)) | Lipid Annotator |
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Chemical Formula | C45H84O16P2 |
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Average Molecular Weight | 943.0864 |
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Monoisotopic Molecular Weight | 942.523459664 |
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IUPAC Name | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O |
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InChI Identifier | InChI=1S/C45H84O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h13,15,18,20,37,40-45,48-51H,3-12,14,16-17,19,21-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b15-13-,20-18-/t37-,40?,41?,42?,43?,44-,45+/m1/s1 |
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InChI Key | NJFASERGTLSFTB-DFWRKXRISA-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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