PtdIns-(3,4,5)-P3 (1,2-dihexanoyl) (ammonium salt) • PIP3C-<wbr/>16; DHPI-<wbr/>3,4,5-<wbr/>P<sub>3</sub>; Phosphatidylinositol-<wbr/>3,4,5-<wbr/>triphosphate C-<wbr/>6 (CAS 799268-62-5) (Inchi key OTVQICSZDVCXQJ-PKNPMILWSA-J) || Cayman Chemical | Supplier
PtdIns-(3,4,5)-P3 (1,2-dihexanoyl) (ammonium salt)
Item № 10008390
CAS № 799268-62-5
Purity ≥98%
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100 µg $40.00 $0.00
500 µg $180.00 $0.00
1 mg $320.00 $0.00

Pricing updated 2015-08-31. Prices are subject to change without notice.

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Description
Synonyms
  • PIP3C-16
  • DHPI-3,4,5-P3
  • Phosphatidylinositol-3,4,5-triphosphate C-6

The phosphatidylinositol (PtdIns) phosphates represent a small percentage of total membrane phospholipids. However, they play a critical role in the generation and transmission of cellular signals.1,2 PtdIns-(3,4,5)-P3, also known as PIP3, is resistant to cleavage by PI-specific phospholipase C (PLC).3 Thus, it is likely to function in signal transduction as a modulator in its own right, rather than as a source of inositol tetraphosphates. PIP3 can serve as an anchor for the binding of signal transduction proteins bearing pleckstrin homology (PH) domains.45 Protein binding to PIP3 is important for cytoskeletal rearrangement and membrane trafficking.6 PtdIns-(3,4,5)-P3 (1,2-dihexanoyl) is a synthetic analog of natural PIP3 with C6:0 fatty acids at the sn-1 and sn-2 positions. The compound features the same inositol and diacylglycerol (DAG) stereochemistry as that of the natural compound. The short fatty acid chains of this analog give it different physical properties from naturally-occurring PIP3, including higher solubility in aqueous media.

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Technical Information
Formal Name 1-​(1,​2R-​dihexanoylphosphatidyl)inositol-​3,​4,​5-​triphosphate,​ tetraammonium salt
CAS Number 799268-62-5
Synonyms
  • PIP3C-16
  • DHPI-3,4,5-P3
  • Phosphatidylinositol-3,4,5-triphosphate C-6
Molecular Formula C21H54N4O22P4 · 4NH4
Formula Weight 838.6
Purity ≥98%
Formulation A lyophilized powder
SMILES O[C@@H]​1[C@@H]​(OP([O-]​)​(O)​=O)​[C@H]​(OP([O-]​)​(O)​=O)​[C@@H]​(OP([O-]​)​(O)​=O)​[C@@H]​(O)​[C@H]​1OP([O-]​)​(OC[C@H]​(OC(CCCCC)​=O)​COC(CCCCC)​=O)​=O
InChI Code ​1S/C21H42O22P4/c1-3-5-7-9-14(22)​37-11-13(39-15(23)​10-8-6-4-2)​12-38-47(35,36)​43-18-16(24)​19(40-44(26,27)​28)​21(42-46(32,33)​34)​20(17(18)​25)​41-45(29,30)​31/h13,16-21,24-25H,3-12H2,1-2H3,(H,35,36)​(H2,26,27,28)​(H2,29,30,31)​(H2,32,33,34)​/p-4/t13-,16+,1
InChI Key OTVQICSZDVCXQJ-PKNPMILWSA-J

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
Stability 1 year
Product Downloads & Resources
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Download Product Insert 91 Kb PDF

Download Safety Data Sheet (SDS) 23 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. Guan, X., and Wenk, M.R. Biochemistry of inositol lipids. Front Biosci 13 3239-3251 (2008).

2. Kashiwada, M., Lu, P., and Rothman, P.B. PIP3 pathway in regulatory T cells and autoimmunity. Immunol Res 39 194-224 (2007).

3. Serunian, L.A., Haber, M.T., Fukui, T., et al. Polyphosphoinositides produced by phosphatidylinositol 3-kinase are poor substrates for phospholipases C from rat liver and bovine brain. J Biol Chem 264(30) 17809-17815 (1989).

4. Tanaka, K., Imajoh-Ohmi, S., Sawada, T., et al. A target of phosphatidylinositol 3,4,5-trisphosphate with a zinc finger motif similar to that of the ADP-ribosylation-factor GTPase-activating protein and two pleckstrin homology domains. Eur J Biochem 245 512-519 (1997).

5. Yang, X., Rudolf, M., Carew, M.A., et al. Inositol 1,3,4-trisphosphate acts in vivo as a specific regulator of cellular signaling by inositol 3,4,5,6-tetrakisphosphate. J Biol Chem 274 18973-18980 (1999).

6. Hamaguchi, N., Ihara, S., Ohdaira, T., et al. Pleckstrin-2 selectively interacts with phosphatidylinositol 3-kinase lipid products and regulates actin organization and cell spreading. Biochem Biophys Res Commun 361 270-275 (2007).

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