| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 01:19:53 UTC |
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| Update date | 2015-07-21 06:59:00 UTC |
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| Primary ID | FDB027108 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | PI(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) |
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| Description | PI(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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. PI(22:5(7Z,10Z,13Z,16Z,19Z)/16:0), in particular, consists of one chain of docosapentaenoic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The docosapentaenoic acid moiety is derived from fish oils, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be 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 by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and 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.
While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. [HMDB] |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C47H81O13P |
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| IUPAC name | [(2R)-3-(docosa-7,10,13,16,19-pentaenoyloxy)-2-(hexadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid |
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| InChI Identifier | InChI=1S/C47H81O13P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(48)57-37-39(38-58-61(55,56)60-47-45(53)43(51)42(50)44(52)46(47)54)59-41(49)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,39,42-47,50-54H,3-4,6,8-10,12,14-16,19,22-23,26-38H2,1-2H3,(H,55,56)/t39-,42?,43-,44?,45?,46?,47-/m1/s1 |
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| InChI Key | YNZSTCIWFMYXJU-OXRHWTJRSA-N |
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| Isomeric SMILES | [H][C@@](COC(=O)CCCCCC=CCC=CCC=CCC=CCC=CCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(O)C1O)OC(=O)CCCCCCCCCCCCCCC |
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| Average Molecular Weight | 885.112 |
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| Monoisotopic Molecular Weight | 884.54147919 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids. |
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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 | Glycerophosphoinositols |
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| Direct Parent | Phosphatidylinositols |
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| Alternative Parents | |
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| Substituents | - Diacylglycerophosphoinositol
- Inositol phosphate
- Cyclohexanol
- Dialkyl phosphate
- Fatty acid ester
- Cyclitol or derivatives
- Fatty acyl
- Alkyl phosphate
- Dicarboxylic acid or derivatives
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Cyclic alcohol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 24767803 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C00626 |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB09918 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Lecithin |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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