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 02:02:47 UTC |
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Update Date | 2022-11-30 19:03:44 UTC |
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HMDB ID | HMDB0009964 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PIP(18:1(11Z)/18:3(6Z,9Z,12Z)) |
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Description | PIP(18:1(11Z)/18:3(6Z,9Z,12Z)) 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)/18:3(6Z,9Z,12Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the g-linolenic acid moiety is derived from animal fats. 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 | CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COC[C@](O)([H])COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C48H86O18P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(50)62-38-40(64-42(51)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)37-61-35-39(49)36-63-68(59,60)66-48-45(54)43(52)44(53)47(46(48)55)65-67(56,57)58/h12-15,18,20,24,26,39-40,43-49,52-55H,3-11,16-17,19,21-23,25,27-38H2,1-2H3,(H,59,60)(H2,56,57,58)/b14-12-,15-13-,20-18-,26-24-/t39-,40+,43?,44?,45?,46?,47-,48+/m1/s1 |
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Synonyms | Value | Source |
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1-(11Z-Octadecenoyl)-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate) | HMDB | 1-Phosphatidyl-1D-myo-inositol-4-phosphate | HMDB | 1-Vaccenoyl-2-g-linolenoyl-sn-glycero-3-phosphoinositol-phosphate | HMDB | 1-Vaccenoyl-2-gamma-linolenoyl-sn-glycero-3-phosphoinositol-phosphate | HMDB | Phosphatidylinositol phosphate(18:1/18:3) | HMDB | Phosphatidylinositol phosphate(18:1n7/18:3n6) | HMDB | Phosphatidylinositol phosphate(18:1W7/18:3W6) | HMDB | Phosphatidylinositol phosphate(36:4) | HMDB | PIP(18:1/18:3) | HMDB | PIP(18:1n7/18:3n6) | HMDB | PIP(18:1W7/18:3W6) | HMDB | PIP(36:4) | HMDB | PIP[3'](18:1(11Z)/18:3(6Z,9Z,12Z)) | HMDB | 1-(11Z-Octadecenoyl)-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphoinositol-phosphate | HMDB | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-hydroxy-3-[(2S)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonate | HMDB | PIP(18:1(11Z)/18:3(6Z,9Z,12Z)) | Lipid Annotator |
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Chemical Formula | C48H86O18P2 |
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Average Molecular Weight | 1013.1332 |
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Monoisotopic Molecular Weight | 1012.528938972 |
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IUPAC Name | {[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-hydroxy-3-[(2S)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid |
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Traditional Name | [(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-hydroxy-3-[(2S)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COC[C@](O)([H])COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C48H86O18P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(50)62-38-40(64-42(51)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)37-61-35-39(49)36-63-68(59,60)66-48-45(54)43(52)44(53)47(46(48)55)65-67(56,57)58/h12-15,18,20,24,26,39-40,43-49,52-55H,3-11,16-17,19,21-23,25,27-38H2,1-2H3,(H,59,60)(H2,56,57,58)/b14-12-,15-13-,20-18-,26-24-/t39-,40+,43?,44?,45?,46?,47-,48+/m1/s1 |
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InChI Key | ARAXYXFWZUUGJF-WDTHDBMJSA-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
- Monoalkylglycerophosphoinositol
- Glycerophosphoinositol
- Inositol phosphate
- Alkyldiacylglycerol
- Cyclohexanol
- Fatty acid ester
- Glycerol ether
- Monoalkyl phosphate
- Dialkyl phosphate
- Glycerolipid
- Alkyl phosphate
- Cyclitol or derivatives
- Fatty acyl
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Dicarboxylic acid or derivatives
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organooxygen compound
- 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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