| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 20:04:29 -0600 |
| Update Date |
2013-02-08 17:23:57 -0700 |
| HMDB ID |
HMDB10064 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PIP2(18:0/18:2(9Z,12Z)) |
| Description |
PIP2(18:0/18:2(9Z,12Z)) 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(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the linoleic acid moiety is derived from seed oils. 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-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate)
- 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate
- 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphoinositol-bisphosphate
- Phosphatidylinositol Diphosphate(18:0/18:2)
- Phosphatidylinositol Diphosphate(18:0/18:2n6)
- Phosphatidylinositol Diphosphate(18:0/18:2w6)
- Phosphatidylinositol Diphosphate(36:2)
- PIP2(18:0/18:2)
- PIP2(18:0/18:2n6)
- PIP2(18:0/18:2w6)
- PIP2(36:2)
- PIP2[3',4'](18:0/18:2(9Z,12Z))
|
| Chemical Formula |
C45H85O19P3 |
| Average Molecular Weight |
1023.0663 |
| Monoisotopic Molecular Weight |
1022.489790074 |
| IUPAC Name |
{[(1S,3S)-2,4,5-trihydroxy-3-({hydroxy[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(1S,3S)-2,4,5-trihydroxy-3-{[hydroxy(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCCCCCC(=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)CCCCCCC\C=C/C\C=C/CCCCC |
| InChI Identifier |
InChI=1S/C45H85O19P3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)59-35-37(61-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-60-67(57,58)64-43-40(48)41(49)44(62-65(51,52)53)45(42(43)50)63-66(54,55)56/h12,14,18,20,37,40-45,48-50H,3-11,13,15-17,19,21-36H2,1-2H3,(H,57,58)(H2,51,52,53)(H2,54,55,56)/b14-12-,20-18-/t37-,40?,41?,42?,43+,44?,45+/m1/s1 |
| InChI Key |
VSNVINGTNHGFPO-WAYLKQQQSA-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
|
| 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 |
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| 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 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027247 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767941  |
| KEGG Compound ID |
C00626 |
| BioCyc ID |
Phosphatidylinositols |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB10064 |
| Metagene Link |
HMDB10064 |
| METLIN ID |
Not Available |
| PubChem Compound |
53480255 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
