D-myo-Inositol-2,4,5-triphosphate (sodium salt)

Cayman Chemical Item Number 10007779

Ins(2,4,5)P3 (sodium salt); 2,4,5-IP3 (sodium salt)

D-myo-Inositol-2,4,5-triphosphate (sodium salt)

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Description

The inositol phosphates (InsP) play a critical role as small, soluble second messengers in the transmission of cellular signals.1,2 The most studied InsP, D-myo-Inositol-2,4,5-triphosphate (sodium salt) (Ins(1,4,5)P3), more commonly referred to as IP3, is a second messenger produced in cells by phospholipase C (PLC)-mediated hydrolysis of phosphatidylinositol-4,5-biphosphate.3,4 Binding of Ins(1,4,5)P3 to its receptor on the endoplasmic reticulum results in opening of the calcium channels and an increase in intracellular calcium.4,5 Ins(2,4,5)P3 is a metabolically stable analog of Ins(1,4,5)P3 that is commonly used to study Ca2+ signaling pathways. Ins(2,4,5)P3 acts as a partial agonist at rat hepatic IP3 receptors, exhibiting 65% of the maximal Ca2+ response obtained with Ins(1,4,5)P3.6

1 Majerus, P.W. Inositol phosphate biochemistry. Annu Rev Biochem 61 225-250 (1992).

2 Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 361 315-325 (1993).

3 Streb, H., Irvine, R.F., Berridge, M.J., et al. Release of Ca2+ from a nonmitochondrial intracellular store in pancreatic acinar cells by inositol-1,4,5-trisphosphate. Nature 306 67-69 (1983).

4 Yoshida, Y., and Imai, S. Structure and function of inositol 1,4,5-triphosphate receptor. Jpn J Pharmacol 74 125-137 (1997).

5 Exton, J.H. Regulation of phosphoinositide phospholipases by hormones, neurotransmitters, and other agonists linked to G proteins. Annu Rev Pharmacol Toxicol 36 481-509 (1996).

6 Marchant, J.S., Chang, Y., Chung, S., et al. Rapid kinetic measurements of 45Ca2+ mobilization reveal that Ins(2,4,5)P3 is a partial agonist at hepatic InsP3 receptors. Biochem J 321 573-576 (1997).

Synonyms
  • Ins(2,4,5)P3 (sodium salt)
  • 2,4,5-IP3 (sodium salt)
Formal Name D-​myo-​inositol-​2,​4,​5-​tris(hydrogen phosphate),​ trisodium salt
Molecular Formula C6H12O15P3 · 3Na
Formula Weight 486.0
Formulation A lyophilized powder
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@H]​1[C@H]​(O)​[C@@H]​(OP([O-]​)​(O)​=O)​[C@H]​(OP([O-]​)​(O)​=O)​[C@@H]​(O)​[C@H]​1OP([O-]​)​(O)​=O.[Na+]​.[Na+]​.[Na+]​
InCHI Code
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​1S/C6H15O15P3.3Na/c7-1-2(8)​5(20-23(13,14)​15)​6(21-24(16,17)​18)​3(9)​4(1)​19-22(10,11)​12;;;/h1-9H,(H2,10,11,12)​(H2,13,14,15)​(H2,16,17,18)​;;;/q;3*+1/p-3/t1-,2-,3-,4?,5?,6?;;;/m0.../s1
InCHI Key
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ZVCVTWVBDIPWPZ-UIEDNGEDSA-K

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D-myo-Inositol-2,4,5-triphosphate (sodium salt) is available in the following screening library:

Size Price Quantity Subtotal
100 µg $49.00 $0.00
500 µg $221.00 $0.00
1 mg $392.00 $0.00
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Pricing updated 2014-04-24. Prices are subject to change without notice.

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