| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 20:02:28 -0600 |
| Update Date |
2013-02-08 17:23:39 -0700 |
| HMDB ID |
HMDB09945 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PIP(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)) |
| Description |
PIP(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates 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 phosphates 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. PIP(16:2(9Z,12Z)/22:3(10Z,13Z,16Z)), in particular, consists of one chain of (9Z,12Z-hexadecadienoate) at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The (9Z,12Z-hexadecadienoate) moiety is derived from fish oils, while the (10Z,13Z,16Z-docosatrienoyl) moiety is derived from fish oils. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. 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,12Z-Hexadecadienoate
- 1-(9Z,12Z-Hexadecadienoate)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)
- 1-(9Z,12Z-Hexadecadienoate)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-phosphoinositol-phosphate
- 1-(9Z,12Z-Hexadecadienoic acid
- 1-Phosphatidyl-1D-myo-inositol-4-phosphate
- Phosphatidylinositol Phosphate(16:2/22:3)
- Phosphatidylinositol Phosphate(16:2n4/22:3n6)
- Phosphatidylinositol Phosphate(16:2w4/22:3w6)
- Phosphatidylinositol Phosphate(38:5)
- PIP(16:2/22:3)
- PIP(16:2n4/22:3n6)
- PIP(16:2w4/22:3w6)
- PIP(38:5)
- PIP[3'](16:2(9Z,12Z)/22:3(10Z,13Z,16Z))
|
| Chemical Formula |
C47H82O16P2 |
| Average Molecular Weight |
965.0919 |
| Monoisotopic Molecular Weight |
964.5078096 |
| IUPAC Name |
{[(1R,3S)-3-({[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2,4,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(1R,3S)-3-{[(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2,4,5,6-tetrahydroxycyclohexyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCC\C=C/C\C=C/C\C=C/CCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCC)COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O |
| InChI Identifier |
InChI=1S/C47H82O16P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(49)61-39(37-59-40(48)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)38-60-65(57,58)63-47-44(52)42(50)43(51)46(45(47)53)62-64(54,55)56/h8,10-11,13-14,16-18,20-21,39,42-47,50-53H,3-7,9,12,15,19,22-38H2,1-2H3,(H,57,58)(H2,54,55,56)/b10-8-,13-11-,16-14-,18-17-,21-20-/t39-,42?,43?,44?,45?,46-,47+/m1/s1 |
| InChI Key |
XDPWHDYPIVOSGA-CNKIVFCLSA-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
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| 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 |
FDB027132 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24767826  |
| KEGG Compound ID |
C00626 |
| BioCyc ID |
Phosphatidylinositols |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB09945 |
| Metagene Link |
HMDB09945 |
| METLIN ID |
Not Available |
| PubChem Compound |
53480140 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
