| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 20:00:47 -0600 |
| Update Date |
2013-02-08 17:23:24 -0700 |
| HMDB ID |
HMDB09847 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PI(18:2(9Z,12Z)/18:0) |
| Description |
PI(18:2(9Z,12Z)/18:0) 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(18:2(9Z,12Z)/18:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-(9Z,12Z-Octadecadienoyl)-2-octadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol)
- 1-Linoleoyl-2-stearoyl-sn-glycero-3-phosphoinositol
- Phosphatidylinositol(18:2/18:0)
- Phosphatidylinositol(18:2n6/18:0)
- Phosphatidylinositol(18:2w6/18:0)
- Phosphatidylinositol(36:2)
- PI(18:2/18:0)
- PI(18:2n6/18:0)
- PI(18:2w6/18:0)
- PI(36:2)
- PIno(18:2/18:0)
- PIno(18:2n6/18:0)
- PIno(18:2w6/18:0)
- PIno(36:2)
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| Chemical Formula |
C45H83O13P |
| Average Molecular Weight |
863.1065 |
| Monoisotopic Molecular Weight |
862.557129254 |
| IUPAC Name |
[(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-(octadecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid |
| Traditional IUPAC Name |
(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-(octadecanoyloxy)propoxy[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O |
| InChI Identifier |
InChI=1S/C45H83O13P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)55-35-37(36-56-59(53,54)58-45-43(51)41(49)40(48)42(50)44(45)52)57-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,37,40-45,48-52H,3-10,12,14-16,18,20-36H2,1-2H3,(H,53,54)/b13-11-,19-17-/t37-,40?,41-,42?,43?,44?,45-/m1/s1 |
| InChI Key |
AXGVJUACAGEWGQ-TYYHIVGOSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphoinositols |
| Other Descriptors |
- Aliphatic Homomonocyclic Compounds
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| Substituents |
- 1,2 Diol
- Carboxylic Acid Ester
- Cyclic Alcohol
- Cyclitol Derivative
- Cyclohexane
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Inositol Phosphate
- Organic Hypophosphite
- Organic Phosphite
- Phosphoric Acid Ester
- Secondary Alcohol
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| Direct Parent |
Phosphatidylinositols |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| 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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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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4.29 +/- 0.39 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
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Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027037 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767732  |
| KEGG Compound ID |
C00626 |
| BioCyc ID |
Phosphatidylinositols |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB09847 |
| Metagene Link |
HMDB09847 |
| METLIN ID |
Not Available |
| PubChem Compound |
Not Available |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
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| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available
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| Enzymes |
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| Name: |
Transmembrane protein 55A
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| Reactions: |
- 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H2O = 1-phosphatidyl-1D-myo-inositol 5-phosphate + phosphate [RN:R08981]
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| Gene Name: |
TMEM55A |
| Uniprot ID: |
Q8N4L2 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Transmembrane protein 55B
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| Reactions: |
- 1-phosphatidyl-1D-myo-inositol 4,5-bisphosphate + H2O = 1-phosphatidyl-1D-myo-inositol 5-phosphate + phosphate [RN:R08981]
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| Gene Name: |
TMEM55B |
| Uniprot ID: |
Q86T03 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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