Analog of PIP3 containing saturated C6 fatty acid chains
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PtdIns-(3,4,5)-P3 (1,2-dihexanoyl) (ammonium salt)

Item No. 10008390

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(1,2R-dihexanoylphosphatidyl)inositol-3,4,5-triphosphate, tetraammonium salt
CAS Number
799268-62-5
Synonyms
  • DHPI-3,4,5-P3
  • Phosphatidylinositol-3,4,5-triphosphate C-6
  • PI(3,4,5)P3 (6:0/6:0)
  • PIP3[3',4',5'](6:0/6:0)
  • PIP3C-16
Molecular Formula
C21H42O22P4 • 4NH3
Formula Weight
838.6
Purity
≥98%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Water: 10 mg/ml
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
InChI=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
Side Chain Carbon Sum
12:0
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    PtdIns-(3,4,5)-P3, also known as PIP3, is resistant to cleavage by PI-specific phospholipase C (PLC).1 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.23 Protein binding to PIP3 is important for cytoskeletal rearrangement and membrane trafficking.4 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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. The Journal of Biological Chemisty 264(30), 17809-17815 (1989).

    2. 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(2), 512-519 (1997).

    3. 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. The Journal of Biological Chemisty 274(27), 18973-18980 (1999).

    4. 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(2), 270-275 (2007).