| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 20:06:03 -0600 |
| Update Date |
2013-02-08 17:24:11 -0700 |
| HMDB ID |
HMDB10157 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
PIP3(18:1(11Z)/20:3(8Z,11Z,14Z)) |
| Description |
PIP3(18:1(11Z)/20:3(8Z,11Z,14Z)) is a phosphatidylinositol trisphosphate. Phosphatidylinositol trisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a trisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol trisphosphates 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 trisphosphates 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. PIP3(18:1(11Z)/20:3(8Z,11Z,14Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. The most important phosphatidylinositol trisphosphate in both quantitative and biological terms is phosphatidylinositol 3,4,5-triphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signalling 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
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| Synonyms |
- 1-(11Z-Octadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4',5'-trisphosphate)
- 1-Vaccenoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoinositol-trisphosphate
- 1-Vaccenoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoinositol-trisphosphate
- Phosphatidylinositol Triphosphate(18:1/20:3)
- Phosphatidylinositol Triphosphate(18:1n7/20:3n6)
- Phosphatidylinositol Triphosphate(18:1w7/20:3w6)
- Phosphatidylinositol Triphosphate(38:4)
- PIP3(18:1/20:3)
- PIP3(18:1n7/20:3n6)
- PIP3(18:1w7/20:3w6)
- PIP3(38:4)
- PIP3[3',4',5'](18:1(11Z)/20:3(8Z,11Z,14Z))
|
| Chemical Formula |
C47H86O22P4 |
| Average Molecular Weight |
1127.0676 |
| Monoisotopic Molecular Weight |
1126.456120484 |
| IUPAC Name |
{[(1S,3s)-2,4-dihydroxy-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphoryl}oxy)-5,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(1S,3s)-2,4-dihydroxy-3-{[hydroxy(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphoryl]oxy}-5,6-bis(phosphonooxy)cyclohexyl]oxyphosphonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(OP(=O)(O)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/C47H86O22P4/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)65-39(37-63-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-64-73(61,62)69-44-42(50)45(66-70(52,53)54)47(68-72(58,59)60)46(43(44)51)67-71(55,56)57/h11,13-14,16-17,19,22,24,39,42-47,50-51H,3-10,12,15,18,20-21,23,25-38H2,1-2H3,(H,61,62)(H2,52,53,54)(H2,55,56,57)(H2,58,59,60)/b13-11-,16-14-,19-17-,24-22-/t39-,42?,43?,44-,45+,46?,47?/m1/s1 |
| InChI Key |
BECIVKAHRHVYFO-FSGBQTISSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
Glycerophosphoinositol Phosphates |
| Other Descriptors |
- Aliphatic Homomonocyclic Compounds
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| Substituents |
- Carboxylic Acid Ester
- Cyclic Alcohol
- Cyclohexane
- Diacylglycerophosphoinositol
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Inositol Phosphate
- Organic Hypophosphite
- Organic Phosphite
- Phosphoric Acid Ester
- Secondary Alcohol
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| Direct Parent |
Phosphatidylinositol Phosphates |
| Ontology |
|---|
| Status |
Expected and Not 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 |
Not Available
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
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Not Available |
| 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 |
FDB027340 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24768034  |
| KEGG Compound ID |
C00626 |
| BioCyc ID |
Phosphatidylinositols |
| BiGG ID |
Not Available |
| Wikipedia Link |
Lecithin |
| NuGOwiki Link |
HMDB10157 |
| Metagene Link |
HMDB10157 |
| 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 |
| 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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