| Record Information |
| Version |
3.5 |
| Creation Date |
2008-09-11 20:03:59 -0600 |
| Update Date |
2013-02-08 17:23:52 -0700 |
| HMDB ID |
HMDB10034 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
PIP2(16:0/16:2(9Z,12Z)) |
| Description |
PIP2(16:0/16:2(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(16:0/16:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of (9Z,12Z-hexadecadienoate) at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the (9Z,12Z-hexadecadienoate) moiety is derived from fish 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-Hexadecanoyl-2-(9Z,12Z-hexadecadienoate
- 1-Hexadecanoyl-2-(9Z,12Z-hexadecadienoate)-sn-glycero-3-phospho-(1'-myo-inositol-3',4'-bisphosphate)
- 1-Hexadecanoyl-2-(9Z,12Z-hexadecadienoic acid
- 1-Palmitoyl-2-(9Z,12Z-hexadecadienoate
- 1-Palmitoyl-2-(9Z,12Z-hexadecadienoate)-sn-glycero-3-phosphoinositol-bisphosphate
- 1-Palmitoyl-2-(9Z,12Z-hexadecadienoic acid
- 1-Phosphatidyl-D-myo-inositol 4,5-bisphosphate
- Phosphatidylinositol Diphosphate(16:0/16:2)
- Phosphatidylinositol Diphosphate(16:0/16:2n4)
- Phosphatidylinositol Diphosphate(16:0/16:2w4)
- Phosphatidylinositol Diphosphate(32:2)
- PIP2(16:0/16:2)
- PIP2(16:0/16:2n4)
- PIP2(16:0/16:2w4)
- PIP2(32:2)
- PIP2[3',4'](16:0/16:2(9Z,12Z))
|
| Chemical Formula |
C41H77O19P3 |
| Average Molecular Weight |
966.96 |
| Monoisotopic Molecular Weight |
966.427189818 |
| IUPAC Name |
{[(1S,3S)-3-({[(2R)-2-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(1S,3S)-3-{[(2R)-2-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,4,5-trihydroxy-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCCCCC(=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/CCC |
| InChI Identifier |
InChI=1S/C41H77O19P3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)55-31-33(57-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)32-56-63(53,54)60-39-36(44)37(45)40(58-61(47,48)49)41(38(39)46)59-62(50,51)52/h8,10,14,16,33,36-41,44-46H,3-7,9,11-13,15,17-32H2,1-2H3,(H,53,54)(H2,47,48,49)(H2,50,51,52)/b10-8-,16-14-/t33-,36?,37?,38?,39+,40?,41+/m1/s1 |
| InChI Key |
WIEOPUXGFYHYFE-SBVOMWEXSA-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 |
|
| 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 |
FDB027217 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767911  |
| KEGG Compound ID |
C00626  |
| BioCyc ID |
Phosphatidylinositols  |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin  |
| NuGOwiki Link |
HMDB10034  |
| Metagene Link |
HMDB10034  |
| METLIN ID |
Not Available |
| PubChem Compound |
53480225  |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |