| Record Information |
| Version |
3.5 |
| Creation Date |
2008-09-11 20:05:01 -0600 |
| Update Date |
2013-02-08 17:24:01 -0700 |
| HMDB ID |
HMDB10095 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
PIP2(18:1(9Z)/20:3(8Z,11Z,14Z)) |
| Description |
PIP2(18:1(9Z)/20:3(8Z,11Z,14Z)) 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(18:1(9Z)/20:3(8Z,11Z,14Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-(9Z-Octadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate)
- 1-Oleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoinositol-bisphosphate
- 1-Oleoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoinositol-bisphosphate
- 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate
- 1-Phosphatidyl-delta-myo-inositol 4,5-bisphosphate
- Phosphatidylinositol Diphosphate(18:1/20:3)
- Phosphatidylinositol Diphosphate(18:1n9/20:3n6)
- Phosphatidylinositol Diphosphate(18:1w9/20:3w6)
- Phosphatidylinositol Diphosphate(38:4)
- PIP2(18:1/20:3)
- PIP2(18:1n9/20:3n6)
- PIP2(18:1w9/20:3w6)
- PIP2(38:4)
- PIP2[3',4'](18:1(9Z)/20:3(8Z,11Z,14Z))
|
| Chemical Formula |
C47H85O19P3 |
| Average Molecular Weight |
1047.0877 |
| Monoisotopic Molecular Weight |
1046.489790074 |
| IUPAC Name |
{[(1S,3S)-2,4,5-trihydroxy-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(1S,3S)-2,4,5-trihydroxy-3-{[hydroxy(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(OP(=O)(O)O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC |
| InChI Identifier |
InChI=1S/C47H85O19P3/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)63-39(37-61-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)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/h11,13,17-19,21-22,24,39,42-47,50-52H,3-10,12,14-16,20,23,25-38H2,1-2H3,(H,59,60)(H2,53,54,55)(H2,56,57,58)/b13-11-,19-17-,21-18-,24-22-/t39-,42?,43?,44?,45+,46?,47+/m1/s1 |
| InChI Key |
FAOGFDQDHJJZBZ-ALXUALIDSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphoinositol Phosphates |
| Other Descriptors |
- Aliphatic Homomonocyclic Compounds
|
| Substituents |
- 1,2 Diol
- Carboxylic Acid Ester
- Cyclic Alcohol
- Cyclitol Derivative
- Cyclohexane
- Diacylglycerophosphoinositol
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Inositol Phosphate
- Organic Hypophosphite
- Organic Phosphite
- Phosphoric Acid Ester
- Secondary Alcohol
|
| Direct Parent |
Phosphatidylinositol Phosphates |
| Ontology |
| Status |
Expected and Not Quantified |
| Origin |
|
| 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
|
| Cellular locations |
|
| 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 |
|
| Predicted Properties |
|
| Spectra |
|
Not Available
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|
Not Available |
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027278 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767972  |
| KEGG Compound ID |
C00626  |
| BioCyc ID |
Phosphatidylinositols  |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin  |
| NuGOwiki Link |
HMDB10095  |
| Metagene Link |
HMDB10095  |
| METLIN ID |
Not Available |
| PubChem Compound |
53480286  |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |